Here’s When First Date Sex Is A Mistake

Name: Bno_sex

Comment: Two questions.. How do I prevent myself from getting attached too fast, and do men care about their partner’s professional success?

A 45 yo recently contacted me online, and we proceeded to have long, intense conversations over the next two weeks, which he initiated. We were both overwhelmed with work, hence the delay in meeting.He was evolved, polite, intelligent, easy to talk to and considerate. He’d left his unhappy marriage and his next gf abruptly dumped him (who he deemed a narcissist) and he was blindsided. About a year later he posted his profile on a dating site, where he met his next two girlfriends, both 25. This gave me pause.

After googling him, to my surprise I discovered that he was a very well known in his field. He also teaches a class at an ivy league school. NYC is full of accomplished people but I’ve never encountered anyone like this. My immediate thought is that this person is WAY out of my league. That said, he was very grounded and we really connected on the phone and had SO much in common.I told him that I had graduated from a state school and he said ‘look, i’m 45, i’m past caring about such things’. WE both felt that we were an intellectual match despite the differential in our status.

We meet, he’s even more attractive, interesting and charismatic than I’d expected. I, on the other hand, was feeling a bit insecure (which I hadn’t on the phone) and was exhausted; I should have postponed the date. I didn’t put my best foot forward. We still had fun, he invited me up to his apt, which was impeccable. Amazing sex, in fact the best sex I had ever had. I contacted him a few times over the weekend, and we engaged in some idle chit chat, but I requested a call which was not returned. We then spoke again and he said he could speak the following day, and called me after I asked him if he was busy and could speak that day. I was in a state of high, high anxiety waiting to speak with him again.It was intolerable. I became way, way too attached far too fast, and I don’t know how to prevent this from happening. I understand that I have to chill out and leave the ball in his court, but until I heard from his I had horrid anxiety.

This is going to work against me, always and I don’t know how to control it. We spoke for a while, were disconnected, he called back and when I suggested meeting later this week he said he was far too busy over the next two weeks and would be for some time, and it was simply too late tonight. I know that he IS extraordinarily busy, I don’t doubt that. He’s working on another project, has two sons, and writing for another site, and I’ve verified this. So yes, I doubt he has time for any relationship. I was discussing dating online in general, and he was giving me tips. Clearly he’s not interested. I point blank ask him what he wants, and why he initiated a relationship that he couldn’t sustain, and he said he had just far extended himself professionally.

I apologized for putting him on the spot,I supposed that if i point blank asked maybe I’d get the answer I wanted to hear. He said it was healthy that we were having the conversation and that it was the adult thing to do, and that he simply couldn’t devote the time to me that he needed. He said he had no idea if we were a potential match since we had only met once. We then hung up, and I immediately sent him an email saying I get it, I can read between the lines, and apologized for backing him into a corner. I said that I know he was being kind and trying to spare my feelings, and that I would have handled it in a similar manner. I did borrow his mittens and leave my hat at his house (inadvertently) and he explained on the phone that we did need to exchange them.

I closed my email by letting me know what time was best to do the exchange and said that if we crossed paths again that would be great, and if not, so be it. No response. I have to go home tomorrow and told him I wouldn’t be home for a few weeks and that I couldn’t get his gloves to him until then (which he needs). I closed by saying we should go to a tapas bar (we’ve both been to spain several times) when his schedule loosens up. This was several hours ago. No response.

When he first contacted me, he had mentioned that even if there wasn’t a romantic connection, that he thought we could still have a valuable friendship. I feel horrible and depressed and can’t stop thinking about what he found wrong with me, why he didn’t want to move forward after we had had a great night. The day after our date, I thanked him for the date, said i had fun, and he replied that he had had fun too, and thanked me for coming out and staying over, but didn’t suggest a future date. At that point I should have just waited for him to contact me again, because the writing was on the wall, correct? I suspect that he would have been open to remaining friends, and I want to believe that I could, but the reality is that it would just be torture for me.

I’ve never, ever met someone who satisfied all my ‘requirements’, and I can’t stop torturing myself about where I went wrong on our date. Did I talk too much, was i boring, was he not attracted to me, was I awful in bed and I’m filled with self doubt. But he did reply to me that weekend, and call me two days later, but only after I ahd requested it.I tried to keep my last email casual and brief. I don’t know where I went wrong, and I don’t want to repeat the same mistakes, nor to I want to give in to this desire to speak to the guy for confirmation the next day that he had fun. The waiting in limbo is awful. And now I can’t stop thinking about him. I suppose I should start dating again to distract myself and remind myself that he’s not the only man in nyc, but I fear that everyone will pale in comparison which will make me feel worse. I just wish I could get out of my own head and move past this. I mean, it was only 2 weeks of intense conversation and one date! I wasn’t with this person for 6 mos.

I know this message is disjointed and probably contains irrelevant information, but I don’t want to sabotage the chance for a second date again, and I believe that would have been a possibility when his schedule relaxed had I not been such a spaz. Should I be dating several men at once to maintain perspective? when he said he had an unbelievably busy two weeks, should I have just said ok, let’s stay in touch and let me know when your schedule eases up? I did say that, but then I called back to ask him exactly where things stood, and as I mentioned, he did say it was a reasonable, healthy conversation and one that we should be having. I really have absolutely no idea what i’m doing when it comes to dating, because I simply haven’t had much practice. the ‘just be myself’ works over the phone, and very well via email,I’m not insecure about my physical attractiveness or personality, but then I freeze on dates. And drink to relax. I know dating requires a strategy, but I don’t know where to start.
Age: 41
City: NYC
State: NY


Yes, this guy recognized that you were way too invested and backed off. But he was probably going to do that any way. At the very least, given how busy his schedule is, he was never going to be able to offer you much in terms of time. You imploded here. You let your insecurity get the better of you and you looked to him to reassure you of his interest and that it was sincere. For that reason alone, you should avoid sleeping with men until you feel more secure in the direction of the relationship. You can’t do casual, which is not a short-coming or limitation. It’s just not for you. If you’re someone who plays scenarios over and over trying to pin  point the exact moment things went wrong, then casual sex or first date sex is not for you.

Here’s  a good rule of thumb. If someone you meet online or off falls well outside of what you typically pull, then approach with caution. You were out of your element and you let this guy and all of his accomplishments and status trip you up.  To compensate for your nerves, you drank. Which of course lowered your inhibitions. But let’s face it. You would have slept with him even if you were sober. You can’t let charm and charisma sway you. You’ve built this guy up in your head to be something he probably isn’t. Now you have to focus on moving on and letting go. Your desire to date this perfect guy says more about how you view yourself than anything else. You’re giving him far more credit than he has earned or that he deserves. That’s why you’re kicking yourself.  If I had to guess, what you sought was his approval more than anything else. You need to figure out why you needed that. Once you determine the source of your anxiety, you’ll be better able to manage it.

I don’t really have much to add here. You know where you went wrong. Now you’re beating yourself up which isn’t going to do you any good.  Forget about your hat. Buy another one. It’s a hat, not a bag of gold dubloons. He doesn’t care about his gloves, either. So don’t use those items as an excuse to stay in touch. I assure you, he is not attached to those gloves. He can buy a new pair.





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67 Responses to “Here’s When First Date Sex Is A Mistake”

  1. msM. Says:

    We’ve all been there. Sleep with the guy “but we had chemistry!” and fall hard for someone we’ve only just met…
    Things turned around for me once I realized it’s not “about the person” it’s about recognizing your needs and going for people who can meet them. We women have some kind of chemical attachment reaction when we sleep with a man, so judgements gets really cloudy….so before you sleep with someone, define what you are after in a relationship, not “how amazing” this guy is. He can’t meet your needs.
    I was in love with someone for years in a situation like that (casual sex for him, “falling in love” for me)…I thought he was “so amazing” and had an exciting career as a music producer…many years later I realized I liked his position in the world and I felt inferior to him at that time and that he was “way above” me…in the end I changed my life so that I no longer felt like I wanted to lead his life/gain his approval like Moxie said…but was living the life I wanted instead.

    • Nicole Says:

      ” it’s about recognizing your needs and going for people who can meet them…. define what you are after in a relationship, not “how amazing” this guy is. ”

      This is such good advice. It should be an obvious first step for all of us, but it’s easy to lose sight of this and get obsessed with “leagues” and who you can “pull”. When I first started dating again, I wasted a ton of time going out with guys who were good on paper, but not right for me. Making a gajillion dollars and running your own business is impressive but no guarantee we’ll have anything in common. Being tall, dark, and handsome is pointless if I’ll never get to see you because you’re busy every weekend.

      OP, we’ve all done the thing where we get attached too soon and it blows up on us. I agree with what you said below about limiting the pre-date texts and calls. Would at least reduce the false sense of familiarity. The first date is still the first date, no matter how much you’ve chatted before hand.

  2. nb1972 Says:

    I also thing that speaking SO much for 2 weeks created an attachment before I even met him. Next time I meet someone online, I’m going to limit phone conversation, even if we have to wait for two weeks, and just go out on the date. When I’ve met someone without all the preliminary phone calls, even when the date was fun and I liked the guy I was able to have casual sex.

  3. nb1972 Says:

    I didn’t feel out of my element with him intellectually, we both conceded that we were a match on that level, it was his level of accomplishment that intimidated me. but moot point.

  4. nb1972 Says:

    And when we spoke so extensively on the phone it very much seemed that he wanted a legit relationship. But it was always at 11pm at night, that’s the only time he actually had time.

    • Eliza Says:

      nb: 11pm at night?! That’s the ONLY time he was free – to what – chat all of 5-10 min. with you? Let’s be frank here–that alone should have been enough of a tip off – in terms of his level of interest. I have met/dated very “busy/successful” men, believe me…and any man reading this can argue or agree…that when a man is truly interested–they make the time – and don’t limit it to 11pm. Also, why are/were you so intimidated by this man?! Did he win the nobel peace prize or discover the cure for cancer. No need to be intimidated…you are placing too much importance on his “accomplishments”…Yes, it’s admirable…but what you need to place merit on is “how he treats you”…and his intentions. That’s if–you truly are more interested in a long-term commitment with someone mutually interested in YOU…not a one night bang…and by the way–if you are OK with the latter…fine, not a sin – to want that. As long as you can recognize the difference and accept it for what it is…and not torture yourself afterwards. You didn’t do/say/or not say or not do anything necessarily wrong. He just wasn’t blown over…next.

    • JulesP Says:

      any guy who only has time to call you at 11pm is basically making a booty call..

      • HammersAndNails Says:

        Get over yourselves ladies. There are plenty of people that work harder and longer than I do and there are certainly times when it’s 11pm by the time I’ve gotten home and eaten.

        You sound like a fool clucking about booty calls that don’t involve any attempt at booty just because of the time.

        • ATWYSingle Says:

          Can I just give an Amen to this? Jesus, the amount of humblebragging that occurs when stories like this pop up is ridiculous. Certain people can’t WAIT to demonstrate just how much better they handle these situations than other women. Please. And, yes, some people don’t have time to talk until 10 or 11 at night. Especially in a city like NYC. In their fervor to prove just how experienced and wise they are, they actually reveal the exact opposite.

        • Goldie Says:

          Yes. This. My ex teaches, not at an Ivy League school, but at a small college in the sticks, that does not have the publish or perish rule. And, in the two years I’ve known him, he was up till midnight on almost any given day, grading stuff, writing stuff up, or whatever it is he had to do for work. I have no problem believing that the guy in OP’s letter actually works as much as he says he does.

        • C Says:

          Its not a booty call until they ask you where you live. Lol.

        • LostSailor Says:

          I agree that in certain professions in NYC, it’s not unusual to work late hours, so it’s not an automatic red flag. OP also mentions he has two sons. Obviously I don’t know how old or what the living situation is, but it’s possible he also had to deal with his kids after work, which would make an 11 pm call all the more plausible.

          Yes, if a man is interested he’ll make the time, but this was before they’d even met in person, so his level of interest was preliminary at best…

        • JulesP Says:

          Not a fool Hammers and Nails… why you so quick to give labels?? Sorry luv but if he had time to speak with the OP at length prior to having sex (she states herself… lots of conversation for 2 whole weeks prior to their meeting up).

          OP then gets demoted to the 11 pm phone call…

          Anyone can find the time to call you if they are interested in doing so.

          Maybe you should get real, huh?

          • C Says:

            Hammer And Nails was gruff in his reply but I believe he is correct.

            The OPs date was calling her at 11pm before the sex. After the date, when she started acting clingy, he simply politely gave her excuses and stopped dating her.

            A booty call has the purpose of setting up a last minute sexual encounter. If he called her at 11pm and suggested he come over (or she come to him), then it would be a booty call.

            Several long conversations over 2 weeks leading up to a scheduled date is not a booty call. Its a date. He met with the OP without the expectation of sex happening. That by definition is not a booty call. The fact that he may have wanted sex or may not have been emotionally available for a relationship doesnt make a date a booty call. It makes it a one-night-stand.

            Calling a complete stranger at 11pm is weird and a little rude, but its not necessarily a booty call unless theres an invitation for sex at the end of the call.

            And its true. NYC is called “the city that never sleeps” for a reason. I had a friend I knew through work tell me to call him any time before 2am because he plays broadway shows until 11pm.

          • Goldie Says:

            Well, in a comment below the OP says that the 11 PM calls were her idea, because of her work schedule. Does it change your opinion re: booty call in any way?

  5. DrivingMeNutes Says:

    You can’t swing a dead cat in this town without hitting some girl who’s had an imaginary relationship with some famous rich guy. I know literally three women who have “dated” John Mayer.

    Sex isn’t causing the attachment. It never does. The OP was already fully invested, gulping the kool aid before sex was even suggested. So, avoiding sex, first date, casual or otherwise, is not gong to solve the problem.

    The good news is that it’s very likely nothing she did or didn’t do that drove him away. He just obviously has lots of options and enjoys exercising them. So, there was never any real potential there to begin with. That said, this behavior would drive anyone away, as a 41 year old adult should know.

  6. nb1972 Says:

    He wasn’t rich or a celebrity; I’m not starstruck by the John Mayers. He was well known in an intellectual field, but a layperson wouldn’t recognize him. And yes, when you have the best sex you’ve had in your life you do become more invested. Had the sex been bad, I wouldn’t have any incentive to see him again.

    • DrivingMeNutes Says:

      Well, the other nb1972 agrees with me: “I also thing [SIC] that speaking SO much for 2 weeks created an attachment before I even met him.”

    • Sarah Says:

      Way to miss DMN’s excellent point entirely. It doesn’t matter that he’s not a real celebrity; in your mind, he was. You clearly landed a bigger fish than you were looking for, front-loaded your date with expectations, made yourself too available, and then revealed your desperation via email. But by that point, he was already gone. There’s no point obsessing over what you did “wrong” to “drive him away.” HE WAS ALREADY AWAY.

    • Mandy Says:

      You’re deluding yourself if you think the reason you were so into him is because the sex was so good. You clearly weren’t just in it for some good sex. You clearly wanted a relationship with this “great catch”. It’s not doing yourself any good to lie to yourself like this.

      Also, most people who are successful intellectuals (ivy leaguers, etc.) have no interest in talking about if their intellect is a match for yours. The simple fact that you brought it up (he said he didn’t care you went to a state school…of course not!) is only going to make someone think you’re insecure.

  7. LostSailor Says:

    What Moxie said.

    B got way too invested in the idea of this guy and then obsessively over-analyzed every facet of the pre-date convos, the date, the sex, and a minute-by-minute analysis of his response times.

    Where I think she really went wrong–besides the obsession–is the “point blank” demand in the post-date call about where the “relationship” stood and “why [he] initiated a relationship that he couldn’t sustain. That, combined with the immediate email apology and essentially telling him she knew the “relationship” was over.

    The thing is, there never was any “relationship.” The guy said it himself: He said he had no idea if we were a potential match since we had only met once. Everything else was in B’s head. She came on too strong to a guy that she knew was out of her league and she knew it would probably backfire, but did it anyway. What I find interesting about B’s letter, though, is that while she gives detail on his relationship history, she reveals no clue about her relationship history, except that she doesn’t have a lot of dating experience. Has she had any long-term relationships? Ever married? I’m going to guess no to both. Which may be part of the problem. B needs to lighten up and chill out.

    But, as a public service, answers to some of the direct questions she poses:

    How do I prevent myself from getting attached too fast[?] See above. Chill. Don’t obsess. And like Moxie said, probably don’t have sex on the first date.

    do men care about their partner’s professional success? Care? perhaps somewhat, but ultimately not really. It’s not a primary element of what men find attractive.

    Did I talk too much, was i boring, was he not attracted to me, was I awful in bed[?] Maybe, no idea, probably he was attracted, and probably not.

    Should I be dating several men at once to maintain perspective? NO! if you can’t not obsess (and some of your comments indicate that you may have done this in the past) over one man, obsessing over two or more would be disaster. Down that road lies madness. And psychotherapy.

    when he said he had an unbelievably busy two weeks, should I have just said ok, let’s stay in touch and let me know when your schedule eases up? Yes. You say you did that, but then immediately called him to ask where things stood. Do the first part; don’t do the second part.

    Other than that. I don’t know what to suggest. Except maybe Xanax, since Quaaludes are illegal…

    • fuzzilla Says:

      **Should I be dating several men at once to maintain perspective? NO! if you can’t not obsess (and some of your comments indicate that you may have done this in the past) over one man, obsessing over two or more would be disaster. Down that road lies madness. And psychotherapy.**

      I agree with everything you said but this. I think being too busy going on dates to obsess about any one guy’s actions is exactly the right thing to do, particularly if she doesn’t have lots of dating experience and needs practice and a better sense of what she wants in a guy.

      Think about it, it’s pretty hard to obsess about four or five different people simultaneously, but I guess anything’s possible…

      • C Says:

        Exactly. Obsession is very singular in its focus.

        I’m ashamed to admit I went through the same thing last year with a super hot high powered guy. Fortunately, i was able to reel in my emotions and not act out my feelings so i’m actually still on friendly terms with ‘super hottie’. I can attest to the fact that you cant obsess about more then one guy at a time. Dating multiple guys doesnt necessarily help avoid fixating, but it couldnt hurt…aside from the fact that you know in your heart that that other guy who took you out on a nice date and is trying to impress you doesnt stand a chance and is just being used.

        Btw, OP, I can tell you how the story turns out when you do NOT ‘blow it’ with a super hottie you obsess about. Mine I think knew from the first or second date he didnt want anything serious but seemed to enjoy the attention and figured I might be down for some casual sex. i wasnt. We went out 5 times, made out, but I never felt comfortable enough to sleep with him because I never had the reassurance I’d ever see him again. Heres the key….I never asked him to reassure me, i just observed his behavior over time and listened to my gut.

        Super hottie still occassionally pings me although he hasnt asked me out since last spring. I friend zoned him the last time he blew me off. I really dont mind chatting with him. He is a nice guy. I now live with my awesome new boyfriend. And you know what….if I ever wound up single again, I wouldnt date super hottie…not even causally. He has nothing to offer me and belongs squarely in the friend-zone.

        Once you meet someone else who you develop feelings for, you will realize just as Moxie said, this guy has little to offer in terms of a relationship and can do much better as far as partners go.

        • fuzzilla Says:

          Right, the obsession doesn’t multiply by adding more options, but instead the whole concept of obsession kind of diffuses and crumbles.

          I do agree with what DMN often says that women dating a lot of guys usually have one favorite and several who fall into the, “Eh, he’s nice” category. I didn’t say dating a bunch of guys at once would solve all her problems, but it would definitely fix that one. She’d be too busy having fun to be fixated about what favorite guy is thinking and why didn’t he get back to her, and and and…

          • C Says:

            I think you are right. It wont solve the problem completely but it may help as you say “diffuse” the obsessive thoughts. I suppose its like any other obsessive thoughts (i.e. thinking about the ex after a breakup), having a friend distract you by taking you out doesnt remove the problem but it does offer enough of a distraction to give you a chance to get a grip and some perspective.

            DMN is right in my experience. I was only ever really interested in one guy at a time (if any at all) whether I was multi-dating or not. In retrospect, when I’ve tried multi-dating, I found myself dating a lot of guys largely to pad my ego (after a breakup). Slight side track….there is this growing contingent of men worried about being used by “dinner whores”. Those girls are few and far between. Lots of us will go out with “a nice guy” we are only marginally interested in to have someone make us feel desirable especially after a breakup.

          • Nicole Says:

            Totally agree with your last paragraph, C. I’ve never gone out with a guy I was “meh” about just because I wanted a fancy dinner or something to do on a Saturday… But I HAVE gone out with guys to take my mind off someone else. Either after a break up, or like Fuzzilla said, to keep from obsessing over a particular guy. I try not to do it anymore because it makes me feel like crap, but yeah, I imagine it’s way more common than girls just wanting a free meal.

        • Goldie Says:

          Agree! I had the same experience 2.5 years ago, well maybe not with a super-hot, high-powered guy, but he was definitely a cool guy who has always had a lot of options. And because he has a lot of options, he was always flaking on me. We both seemed super into each other after the first two dates, but then he messaged me saying “been thinking about you all day!!” and then I didn’t hear from him again for 24 hours. That’s when I knew, from previous experiences with this type, that I had to step back, cool off, and not get attached, unless I enjoyed being in a world of pain. We also had five dates (not counting a Saturday night one that he canceled last minute… yup), I admit I went to his place once, but made sure to stay cool and unemotional about the whole thing, and ultimately chose someone else to get into a LTR with. We still keep in touch, we’re still friends, but that’s what we’re going to be, friends. At this point, like you said, I am not interested in dating him and he’s probably just fine with that. Plus he’s a good friend to have.

          • C Says:

            Exactly! They are genuinely nice, personable guys. Thats part of why they are so popular. The guy i dated had been super helpful to me about a business question I had months after we stopped dating.

            You nailed your guys motives faster than i did. Been thinking about you all day thats why im sending you a text instead of setting up a date or calling. lolol. Thats such a cheeseball player move.

    • Eliza Says:

      LSailor–well said. Obsession over what? Basically a stranger in the night? and being intimidated–why? Because he attended some ivy league? Please. The worst thing to do is put ANYONE on some pedestal. Their egos become the size of Mt. Rushmore…and one also comes across extremely insecure–which is not sexy at all – for any gender. And if you can’t hold more than 1 drink – before your judgment gets clouded–then guess what? Don’t have more than 1 drink! have your wits about you.

  8. Damien Says:

    “…best sex in my life…” LMFAO.

    How many times have I heard this line, here and elsewhere, from women who meet the complete package, go out for drinks that turns into dinner, and then a mind-blowing dessert, not once, but three times, and then it’s a distant memory.

    Ever wonder where these guys get the practice to be so good? Ever wonder how you can pull someone out of your league? Ever wonder why a guy that is the complete package is still out there? No, because the intoxication of being weak in the knees makes it a high, and we know what a high does to judgment and common sense.

    • C Says:

      “Ever wonder why a guy who is a complete package is still out there?”

      Brilliant! Thats the best line Ive read in this blog! Unless he was just widowed last week, he is a goofball like the rest of us.

      • BTownGirl Says:

        “…he is a goofball like the rest of us.” Oh, I love this line so much! I think we can all agree that putting dudes on pedestals is not a great idea, am I right? :)

      • Eliza Says:

        C: Every guy is a goofball, UNTIL he meets the right woman – for him!

      • HammersAndNails Says:

        Is that what you took away?

        Why is he still single? Because he likes it that way.

        • C Says:

          What I took away is exactly that but from a different point of view.

          If I’m interested in a relationship, then by definition, my “total package” is also interested in a relationship.

          When I’ve met very good looking, accomplished, personable guys who were emotionally unavailable for a relationship (i.e. a guy who is recently separated, or a nearly 50 year old who was perpetualy single), thats not what I would call a total package. That at best is a “trip to disneyland” meaning a fun way to waste an evening. Its the equivalent of you taking a really hot girl out who you know will never sleep with you.

          • HammersAndNails Says:

            You think I’d consider wasting time and energy on a woman I’ll never sleep with ‘a trip to Disney land’ lol.

          • C Says:

            HmmerAndNails – umh….thats my point….OP’s super hot guy is just as much of a waste of time for her.

    • Goldie Says:

      “Ever wonder where these guys get the practice to be so good?”

      Ahhh yes. If I could upvote this comment multiple times, I would.

      The two 25yo ex-girlfriends should’ve also been a dead giveaway.

  9. BigCityLife Says:

    He fed you a bunch of lines about his busy life so you would always answer the phone late at night where you “totally connected” then he finally had a free night where he wasn’t busy and you “totally connected” over dinner/drinks where he then conveniently brought you back to his place for sex. Guys don’t loan clothing items to women that they don’t absolutely need back. A pair of gloves is $20 and he gave them/ “loaned them” to you as a way to get you out the door.

    His hope waas that you would be cool with a casual sex relationship. He has no expectation of getting his gloves back. Walk away with your dignity.

    • msM. Says:

      Yeah I agree. Also the fact that he told the OP he’d had not one, but two 25-year-old girlfriends should tell her that settling down was not in the cards for him.
      It sounds like this guy has a perfect bachelor pad and is quite experienced at this. A man his age, with the level of success and presumably a nice apt in a good neighborhood in NYC who dates 25-year-olds is good at doing this. You were not the first and you will not be the last.

      Men like that online have lots of options as he himself told you, and I agree that the “busy” thing is another word for “not available”. I don’t think he is a bad person at all, really, he tried to put it the best possible way that he was not available. As we have all discussed on this website if you want a “relationship” you have to make that explicit, and consider that before sleeping with someone. Sex does not equal a relationship. We know that by now:) Meanwhile he got (laid) what he wanted and you are left wanting more…

      I have read many websites about dating and they all say when men are interested the will show it in ACTIONS not words, and it will NOT be ambiguous. This sort of encounter is intoxicating because it allows you to imagine a life that appears glamourous to you and to escape the perceived mediocrity of yours. (I have been there myself and I can feel your awe at his “flawless” apartment” and cool job…). The fact that the OP sees herself as below his league is an issue. separate from the encounters we are discussing.

      I would say that if you are after a relationship the only way to go about it is to try and go on as many dates as you can. Until you find someone who will actually be present in your life. This is also a good antidote to the depression that ensues after the rollercoaster experience you have just had…you just have to try and put yourself out there for real.

    • Eliza Says:

      Exactly! lol…the old cliche – of using an item “left behind” – from either party is rather pathetic, to say the least. And if it’s an item of any value–I’m sure you can send it to him, without interracting with him directly – at some Tapas Bar! sheesh. Or if he lives in some bldg. with a doorman leave it there. I’m sure the OP can afford another hat too. Why oh why do some women – grasp at straws!! why ladies?? Isn’t your self worth and dignity worth more than that? And if he lent them to you–keep them…he won’t claim bankruptcy over a pair of gloves or hold you accountable – I am sure of this. Move on. You will/can meet someone else that reciprocates your level of interest.

    • LostSailor Says:

      Ha! On another note, nearly every woman I have had any kind of non-fling relationship with over the years and who have stayed over at my place seemed to have needed to “borrow” some article of clothing either overtly or inadvertently–a t-shirt, sunglasses, gloves, scarf, even once a pair of shorts–that they never actually returned even after the relationship ended.

      I’ve never asked for any of them back…

  10. Nb1972 Says:

    A bit cynical, no? I lost my gloves mid date the night before; it was freezing, hence he lent me his. No ulterior motive there. Had nothing to do with getting me out the door. I’m very familiar with his job (s)/schedule/family life and yes, he is extraordinarily busy. I agree that he just wanted something casual but he wasn’t manipulative or throwing me lines. He was pretty straightforward.

  11. Nb1972 Says:

    *Well, the other nb1972 agrees with me: “I also thing [SIC] that speaking SO much for 2 weeks created an attachment before I even met him.”*

    Yes, I was already invested; what I said was that the sex made me MORE invested. And yes, i’ve had enough sex to know what’s been the best of my life. That would have been true of him regardless of all the extraneous stuff.

  12. Ben Iyyar Says:

    The writer made a good faith effort with this gentleman and failed, for so many reasons. She is 41 and seems to really want a settled relationship, this fellow she went out with had all the positive aspects any woman would want so she made the effort. In this case, and I emphasize this case, it went south quickly, which is good, at least she wasted very little time. After this experience, and some advice, she can resume her search for her partner with more care, understanding, and due diligence.

  13. D. Says:

    A few observations.

    1. Do guys care about a woman’s professional accomplishments? Generally, no. Or at least, not as much as it often seems women care about guys’ accomplishments. There’s sort of a baseline above which a woman needs to be, but that baseline varies from guy to guy. For the most part, though, saying “AND I have an Ivy League degree!” doesn’t really advance you very much with men. It’s nice that it’s true, but it’s not the kind of thing that’ll tip the balance in your favor if he’s on the fence about you.

    2. Not having sex with the guy will not remove your anxiety. That said, it probably will intensify your anxiety, so avoid casual sex. First date sex is casual sex, by the way, no matter what kind of “connection” you feel. While we’re on the subject of “connections,” there are different kinds of connections. You can have an initial connection that goes nowhere. (Or a spark, or vibe, or chemistry, or whatever you want to call it.) Sometimes it’s just a flash in the pan. Other times your connection will deepen as you get to know each other. It’s important to keep that in perspective when dating someone, especially early on. You don’t have an “amazing connection.” You have initial chemistry, and initial chemistry can all too often be fleeting.

    3. You need to get at the root of your anxiety and figure out where it’s coming from, at least with regards to dating. Maybe you’re an anxious person by nature, but as far as dating goes, this behavior is counterproductive. My guess is that this guy was fine initially, and then you started getting all clingy on him, sending multiple texts, calling him, trying to get him to ease your anxiety by saying how into you he was. When that happened, he knew he didn’t want anything long-term with you.

    Now, as Moxie said, chances are he’d have arrived at that conclusion eventually anyway. There’s plenty in your description of him to suggest as much, at least. Dating women 20-years his junior, being relatively recently divorced and then blindsided by a girlfriend dumping him…these things all suggest someone who is not really up for opening himself up to a serious relationship.

    But all that aside, he might’ve been up for some fun dating in the meantime, until he determined that you aren’t the “fun dating” type. In other words, you wanted a serious relationship overnight. When you talked about your “relationship” after one date, understand that this, to men, is code for “I’m insane. Steer clear of me, or there will be much drama.” Fair or not, accurate or not, that’s what men will hear. How do I know? Because I’ve been the guy in this situation and I did exactly what he did: I called it off and made no effort to contact the woman further. It wouldn’t have mattered if she had a pair of my gloves or I had her hat. I’d have seen the “let’s meet to exchange our stuff” as (A) evidence of further inappropriate attachment (what, like I’m returning your record collection to you after a big breakup? It’s gloves and a hat!), and (B) a ploy to get me to meet in person so I can be put on the spot with uncomfortable “But what did I do wrong?!” style questions that I don’t want to answer.

    To be honest, reading the story, it struck me that what you were into wasn’t the guy. You didn’t even know the guy. You were into the fantasy of the guy, and if that’s the case, you need to ask yourself why that’s so seductive, and what it is you’re trying to accomplish. My guess? You want to be paired up. Badly. You are likely also terrified of things not working out and ending up alone, and that, in turn, drives you to try to force the issue and/or control or at least predict the outcome. It’s why you sought reassurance from him about where things were going after one date, and why you got so attached, again, after one date.

    I don’t know how exactly you’re going to do this, but my advice is to reconcile yourself to the notion that you very well may end up alone. From my experience, it’s only by confronting and accepting the things you fear that you’re able to let go of the fear about it, relax, and just enjoy yourself. But one way or another, you’ve gotta get a handle on the anxiety in the dating context.

    • mindstar Says:

      “When you talked about your “relationship” after one date, understand that this, to men, is code for “I’m insane. Steer clear of me, or there will be much drama.” You absolutely nailed it D.

  14. Goldie Says:

    This is why, when I meet a guy who appears to be far out of my reach, I am super wary, and make sure not to get attached. Don’t get me wrong, I’d still go on a date, because that’s guaranteed to be a great time, and give me cool stories to tell afterwards – I love meeting people from all walks of life and hearing about their life experiences that I otherwise wouldn’t know much about; I just wouldn’t expect a second date. With this guy’s credentials (including the best sex evah), can you imagine HOW selective he probably is? I’m actually not even sure if I’d want a partner like that – one I’d always feel insecure around, always feeling like I have to prove that I’m worthy of his time. Screw that; life’s too short for that.

    The closest thing I had to an encounter like this in my Midwestern town was when a guy 7 years younger contacted me on OKC this fall. He went to NYU, he’s a film major, he is actually a film producer (I verified this – my 18yo son just happens to own a DVD of a movie that this guy helped produce), and very easy on the eyes… IOW, out of my league. He asked for a date, we set it, and I went on our first date knowing full well that it will be our last one. We chatted about things that interested both of us, including my and my son’s upcoming trip to NYC to look at colleges. We both had a good time, he never contacted me again, it was fun, end of story. I don’t regret going. We didn’t go to his place though. But if we had, I probably wouldn’t have regretted that either; and wouldn’t have expected further contact anyway.

  15. Nb1972 Says:

    I didn’t use the word relationship with him. I’m not that daft. I asked him if he wanted to go out the following Friday (7days away) and ge explained what he had to do and would be busy for about two weeks. Yes, I should have said fine and left it at that.

  16. btrflynaia Says:

    He thought you were a five star cling on! I met a nice man in December. We had a ton in common. But, after he starting becoming anxious after 5 days together that I had to work for 3 days (12hr shifts) and would not be able to see me. Red trucks started going off. Unfortunately, I had to break things off. I can’t fix another’s insecurities. Nb1972 it’s time to evaluate yourself.

  17. Nicole Says:

    “I’ve never, ever met someone who satisfied all my ‘requirements’ ”

    OP, I really think this attitude might be part of your problem. You’re in NYC and this is the ONLY guy there who’s right for you? I’m on okcupid in Dallas and I get 10+ messages a day from men who satisfy all my ‘requirements’. Doesn’t mean I’m going to hit it off with all of them, but they meet the basic criteria I’m looking for in terms of looks/age/job/education/interests/whatever.

    Getting this wrapped up in one guy after one date isn’t healthy. From what you wrote, it sounds like he was really busy and freaked out when you seemed needy and clingy after your date. Was he out of your league? Who knows. Would he have called you again? Who knows. But you need to avoid seeing any guy as “the guy” that early, because it made you lose your senses.

    • D. Says:

      This. You aren’t into the guy. I mean, how could you be? You barely know him at all. No, you’re into your fantasy of what he’ll be for you. You’re objectifying him, basically. He ceases to be a real person, and instead becomes “Fantasy Guy.”

      This is fundamentally no different from guys who get hung up on the “Manic Pixie Dream Girl.” It’s less about the person sitting across the table from you, and more about how this person slots into your fantasy of what perfection is.

      In my experience, most of that stuff is about creating a sense of order and predictability to the universe and relationships, because that somehow removes the uncertainties from your life, and its the uncertainties that drive anxiety. Until you can learn to accept the uncertainty (not merely intellectually/rationally, but emotionally as well) and just ride it out, it will continue to master you.

    • Goldie Says:

      I would add that, if you know that a person satisfies all your requirements either after first date, or before you two have even met, then your list of requirements needs some serious revising. While the looks/age/job/education/interests stuff does allow a guy to get his foot in the door, none of those things indicate if he is going to be a good partner for me. That is determined by his personality, core values, lifestyle, and how well he and I fit together on a personal level, and there’s no way to know any of those things until we’ve spent a good amount of time around each other.

  18. Grizzly Says:

    “Do men care about their partner’s professional success?”

    No. Well, maybe not 100% of the time, but almost never.

    It never ceases to amaze me how so many chicks can’t pick up on this kind of situation. Its so obvious. Its like smacking your face on the Sears Tower because you looked away for a second and didn’t notice it.

    He was looking for a quickie because he was in a dry spell, and the LW was his release. Here’s how you can tell this was a classic pump ‘n’ dump:

    1. Highly educated, attractive, charismatic, interesting.

    2. In a position of authority in his field and teaches at an Ivy League school.

    3. Dates chicks 20 years younger and is great in bed.

    4. Has sex on the first date with a desperate neurotic middle-aged woman who has a long list of nit-picky requirements, and who is way below his league, then cuts off all communication.

    5. Friendzones her on the FIRST communication, before they ever meet. PUAs all over the Internet are probably bowing to this guy and chanting like Wayne and Garth “We’re not worthy! We’re not worthy!”

    Ladies, take it from a man. If YOU YOURSELF realize that he is way above your league, then you will never be anything more than a quickie. The LW’s solution is pretty obvious. Unless she wants her only companions in life to be cats and other women, she needs to throw out her requirements and be realistic about whom she can and can’t attract.

  19. Yvonne Says:

    I find it interesting that, despite the red flags, we think that guys like this are so extraordinary, as if the red flags don’t really exist. The OP needs to refrain from getting so enraptured by a man’s professional success, that she is blind to his flaws on a personal level. Divorced guy, dumped by “narcissistic” (of course!) ex. His next two girlfriends are both 20 years younger. This man has “mid-life crisis” written all over him.

    If you want to be in a relationship, then slow the pace down, and spend time in each others’ presence, actually dating. Get to know someone as a person first, as a friend, and see what they are capable of. I’m sure this man is busy, but sometimes people use that as a convenient excuse to avoid getting more involved with someone. A busy man who wants to be in a relationship will make time for a woman. And Mr. Busy-Big sure didn’t have any problems hanging on the phone for “long, intense conversations” for 2 weeks prior to the date.

    Any man who tells you that he is “far too busy over the next two weeks and would be for some time”, is trying to let you down easy. He doesn’t give a crap about his mittens, or getting your hat back to you. Especially if you haven’t had much practice dating, then spend some time going on real dates with a variety of men. Try to avoid drinking too much too.

  20. Howard Says:

    This is not going to be a pretty analysis, but this is what I think happened. Busy is only part of it. After all, before he met her, he found the time to chat and he found the time to go on a date with her. So, in spite of being busy, he can find time. But, here’s where it gets tricky, only if she turns out to be amazing.

    What is amazing? Well this guy wasn’t getting sex because of his busy schedule. However, he is pretty good at it. So he has a very high bar on what good sex means from a woman. I guess the OP did not meet that bar. There are lots of reasons that could have happened. I believe nervousness could be a big factor. I’m a man, and first times are always nerve-racking for me. I think almost every woman I have been with, have told me, my second time was way better than my first.

    I have done the Ivy-League thing too, and don’t totally believe what he said. My old college associates, especially professor types, can be too elitist for my taste. It kinda works like this. They would do the woman from a state school, if she were amazing in other categories. Looks, extraordinary charm and sex counts for a lot. But if a woman from a state school is average there, they would probably not do long term.

    I keep saying to people on this board, “High-profile and hot is a competitive arena to play in”. It has nothing to do with gender. If you are a man and want to go after a really “out of your league” woman, be ready for the worst. If you are a woman going after the “out of your league” man, also expect the worst. Just treat it like playing the lottery, and if you are pleasantly surprised, then great, else just do “next”, in your head, when the jig is up.

    The next big issue is first date sex or sex early in the relationship, followed by clinging like saran wrap. It never works. I don’t care who or what the guy is, it’s the worst thing a woman can do. All relationships take time to build, irregardless of when you have sex. It’s delusional to imagine that sex, no matter how great it is, will somehow totally bypass relationship building.

    My advice to the OP is to avoid sex that early, but don’t wait too long either. Too long can also build too much nerve wracking tension where you create lofty expectations that can never be met. And if you ever have sex that early in a relationship, don’t imagine the walk down the aisle. Be cool, and keep building the relationship. Also,if you do that early, don’t imagine pulling back the sex will work. You can’t get someone used to being one way then trying to use that thing like a weapon.

    I know a lot of guys who had early sex with their wives or long time girlfriends. Guys who are used to getting lucky early don’t necessarily see women who have sex with them early as loose. They place their success on their skill or looks or high-profile status, rather than the woman being loose. So if a woman stays cool after early sex, she still has all the same chances as if she had sex later.

    There is a myth that if a woman deliberately holds out on an in-demand guy she will somehow mystify him into thinking she is special. That is not necessarily true. I don’t, in any way, believe a woman should throw herself at such a guy, but there is a natural order to things unfolding organically.

  21. Yvonne Says:

    Also, “I contacted him a few times over the weekend, and we engaged in some idle chit chat, but I requested a call which was not returned.” No. Don’t do that. After any first date, sex or not, best to let him contact you next. If he wants to, he will.

  22. nb1972 Says:

    Yes, this is all true, except the school part; he did his undergrad at a state school and we did click intellectually,and I’m successful in my field; that wasn’t the issue. It was my clinginess and insecurity and belief that he wanted something long term simply because we spoke 2 hrs/night for 2 weeks prior to the date. My expectations weren’t aligned with reality. His midlife crisis was SO obvious and did cross my mind; I just decided to ignore it. His last long term gf (narcissist) was nothing spectacular to look at, nor was his ex wife, who, surprise, surprise, he described as borderline, but I’m sure after this confidence crisis and realization that he could pull 25 yo’s, well, why wouldn’t he? He also split with his last 25 yo gf of 8 mos because she became attached and wanted babies. Not sure why that surprised him… Red flags were EVERYWHERE. He liked the chase, and that’s where his interest in me began and ended. I also projected qualities onto him that he didn’t have for the wrong reasons. I’ve dated plenty of wealthy, high profile men (I work in the finance industry) and I’m not starstruck by them. I just happened to respect his particular field and his prominence within it. Upside is that I’m lucky this imploded fast and I learned some valuable and obvious lessons before I became more attached, because this was never going anywhere.

    • C Says:

      Good for you in realizing all of this. I hope this all makes it easier to move on. And btw, i find it suspect that the problem was always with his exes (as someone else mentioned). That one was a narcissist; that one was borderline; this other one: clingy. Frankly anyone who deems every woman who leaves him as crazy is probably at minimum a narcissist himself. Anyway, “pulling” a 25 year old at 45 isnt all that magical. They dont all look like Magen Fox and dont all have successful men clamering for their attention.

      Unfortunately it hurt, but I’m sure you wont make the same mistake again. As much as folks are giving you a hard time, I think most of us have made a fool of ourselves over some hottie at some point.

  23. nb1972 Says:


    : 11pm at night?! That’s the ONLY time he was free – to what – chat all of 5-10 min. with you?

    The timing was, in part, because I’ve been working so late, and we spoke for hours, not 5 or 10 minutes. We did speak a few times midday, but most of the time it was after 10, which was also my choice.

  24. nb1972 Says:

    8hammers and nails
    *Get over yourselves ladies. There are plenty of people that work harder and longer than I do and there are certainly times when it’s 11pm by the time I’ve gotten home and eaten.
    You sound like a fool clucking about booty calls that don’t involve any attempt at booty just because of the time.*

    Yes, there was no attempt to meet at 11pm for a booty call. We had set a potential date about 2 weeks out because of our schedules.

  25. nb1972 Says:

    Why the hostility over the gloves? HE suggested we exchange our stuff on the phone; I replied via email and have not mentioned it since. It’s a non issue.

  26. nb1972 Says:

    RE the teaching at an Ivy league school.. I didn’t consider that a huge accomplishment, it was an addendum. I left out the operative ones to protect his privacy. I’ve dated plenty of men who went to Ivy league schools, along with a professor. These men are the norm in nyc, not the exception.

  27. msM. Says:

    One thing I learnt from Moxie was to tone down the expectations and to avoid too much communication *before* meeting someone via online dating. This can create all kinds of false ideas and expectations.

    Once you have the basics covered, wait until you meet someone. It has happened to me to build up someone in my head only to be disappointed. It is easy to be thinking of someone as an escape, detached from reality, when in fact dating *is* about confronting realities, and about fitting love into the realities of our lives, however painful it might appear to be.

    • C Says:

      I think many of us have made the same mistake. Truth is no one can ever live up to the imaginary person we create in our minds when we are given limited contact with a love interest.

      I had a a long distance boyfriend years ago as a young pup. He was a coworker I started dating 2 weeks before he took a new job and moved away…certainly not a complete stranger! We talked on the phone twice a week which gave me the opportunity to build up “my man” as this fun, sympathetic, loving, sex god who adored me. After three months of this, “my amazing man” came “to visit me”. Only he wasnt coming to visit me! He came to visit our coworkers: to see old friends and continue playing out old drama with old exes. Together again, I couldnt help but think, “Why can’t you be as great as I thought you were?!” No joke! Lol.

  28. ATWYSingle Says:

    Okay, so, here’s why you shouldn’t be getting involved in casual relationships with guys you meet on sex sites:

    You wrote this letter, too. Dude, back away before you find yourself in the same situation you frequently seem to end up with, where the guy has sex with you then blows you off and you spiral out of control. I’m not trying to be mean. You do not have the casual sex/FWB gene. Your anxiety makes those situations very triggering for you.

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