This Is How To Get Past The First Date

Name: Cheerios
Age: 33
State: NY
Question: So here’s my latest dating gripe. A guy from an online dating site wrote me and immediately wanted to exchange numbers. I’m down for that since I’m a fan of meeting up as soon as possible to test the chemistry waters. We exchanged two emails, and then spoke on the phone. The guy called me at 10:30pm on a Monday night, though he did ask first if that was ok (being it was so late) and I agreed (maybe I shouldn’t have). We had about a 10 minute conversation at most, and from that short talk he determined we wouldn’t click. Really? Now we have a 10 minute window (on the phone no less- not even in person!) to make an impression??? The conversation was fine, a little awkward as most first phone calls can be, but nothing overly bad/good. I’m just so over the online thing. Everyone is so judgmental so quickly. Of course I’m wracking my head to think what I could’ve said that would’ve turned him off, but have no idea. He did notice I sounded tired on the phone (it was 10:30!), but we talked about where we grew up, went to college, a little about our jobs, about our birthdays, & that’s about it. Can’t figure it out.


Of course I’m wracking my head to think what I could’ve said that would’ve turned him off, but have no idea.

That’s because you probably didn’t say anything particularly offensive or off putting. Like I’ve said before…the phone step is just a way for people to find something wrong with someone so that they don’t have to meet them.

Here’s a very simple rule of thumb. People who want to meet people meet people. They don’t want to hop on the phone after two emails at 10:30 at night. You were being set up to fail.

He did notice I sounded tired on the phone (it was 10:30!), but we talked about where we grew up, went to college, a little about our jobs, about our birthdays, & that’s about it. Can’t figure it out.

So then you discussed nothing at all relevant or interesting? Gee, can’t figure out why he might have determined you were boring. I mean, other than he sounds like he has no conversation skills and has poor social skills himself. This is why the phone step is a waste and if rapidly becoming another red flag.

We had about a 10 minute conversation at most, and from that short talk he determined we wouldn’t click. Really?

Let me let you in on a little secret. This guy was never going to meet you. He truly believes that he’s interested in meeting someone, flexible and oh so engaging. In reality he’s a snooze who is afraid to meet people in person.

It’s funny. The people who bring the least to the table seem to have the most opinions, disclaimers and required steps. They think everybody is boring, weird, strange, etc. Nope. They’re just hoping people won’t stick around long enough to see all their warts.

Stop being so boring and uptight. Develop a personality. Have fun. Stop going into every date with a checklist and all these phony opinions you’ve developed. Case in point:

I am not recovery, however, I personally don’t like to drink, perhaps because I am the daughter of someone who went through recovery?  And also just don’t crave alcohol or find it enjoyable…and it seems it’s very hard to find men out there that don’t drink, or suggest going for a drink on date 1, 2 or 3.  And if you don’t drink with them?  Some men don’t find it enjoyable.  Perhaps I am dating the wrong men.  I just find that society today is very fixated on getting intoxicated or drinking to be social…when I can have a blast and be social without drinking at all. – Eliza

Good grief.  Have a cocktail! You don’t have to get hammered. But geez…loosen up. Sip your drink and make conversation. Leave your judgey uptightness at home. It’s a first date. Not a Dick Cavett interview. The problem isn’t that they like to drink. It’s that you don’t. So either become more accommodating or only date men who don’t drink. Sheesh. Same goes for you guys with a chip on your shoulder about women who get alimony. Until something directly affects you or creates a problem, get over it. Some of you look for stupid things to hang your hat on and so you can blame other people, when the blame should fall squarely on your shoulders.

One thing that I notice when reading  profiles is that many of people either try way too hard to sound dynamic or come off like complete shut-in bores. You have to find a middle ground. Lean how to be engaging, both in writing and in person. Try to make your likes and hobbies sound interesting and, dare I say, sexy.

Here’s an example:

A quick glimpse into a day in my life:

*Early morning work outs that get you energized for the day ahead

*Fumbling around my kitchen trying to make blueberry pancakes with bananas

*A hot shower that includes coconut scented body salts (or vanilla. I love both.)

*Walking my eager pooch who manged to snag a couple bits of faux blueberry pancakes

*A few hours scratching things off my To Do list like call back Client X, write up a spec sheet and send you a flirty text

*Kicking off my shoes after a day’s work to jump into a sundress and flip flops to meet a girlfriend for wine and catch up at her place.

*Joining friends for a Mash-Up potluck dinner

*Catching up on the latest episode of Fringe, The Walking Dead or Mad Men

You can take an ordinary life and make it sound intriguing. It’s all in the way you write it.This woman sounds fun, laid back, sexual, active and social. That’s the woman that men like to date. She’s also not afraid to encourage a man to picture her naked. That’s what men want to see.

Same goes for the guys. We don’t want to hear about your job or your travels. I completely agree with the people who roll their eyes at those who list out all the places to which they’ve traveled. Don’t care. And we definitely don’t want to hear about your kids.  Leave the self-important humblebraggery for your blog or diary. I remember reading a guy’s profile once. He had posted quotes from women berating him in response to his profile. He was so proud of being considered an asshole. Not attractive.

Oh, and another tip? Stop listening out all the bands you love and books you’ve read and your favorite movies. Instead, use quotes from songs, movies, and books. That’s a great conversation starter and will keep people invested in your profile.

Of course, you should actually include things that you do regularly. Don’t lie (too much.) But hey, a white lie wouldn’t hurt, as long as it doesn’t involve you conquering a goal that there is no way in hell you have even tried to reach let along worked towards before. interesting.  Make people want to hang out with you and think you’re fun. And then? Be fun! Forget the interview questions. Forget the rules and the lists. Go get tipsy! Make out at the bar. Play music on the juke box. Dance a little. Try a food you’ve never had. Take a risk!

Here’s another suggestion….don’t ask someone what they do for a living either in the initial email stage or on the first date. Let them tell you what they do. I double dog dare some of you to do that. No, you’re not making conversation. You’re trying to find out what their financial situation is before you’ve even kissed them.  Do you know why you do this? Because you have stunted social skills. I’m telling you…that need to size everybody up and down before you even determine if there’s a mutual attraction is keeping you single. If you can financially support yourself, and the other person doesn’t appear to be a deadbeat leech, then there’s no reason to focus on their financial/professional situation so early on in the relationship.

Learn how to make conversation. Not polite party conversation, either. Talk about things you love, that get you excited. Show your dates that side of you. Who cares if they know nothing about it?? Educate them. Make them want to learn more..from you.Encourage them to talk about stuff they enjoy. Forget about the interview questions!

Stop worrying so much about making a stellar first impression. Don’t go overboard, of course. But don’t be so worried that they won’t like you because you snort when you laugh, love Big Brother enjoy a greasy cheeseburger.

Bonus tip? Ladies, wear something fun and flirty on your dates. Sundresses are a big plus. Men LOVE sundresses. I just bought about 4 new ones that I can not wait to wear. Show a little skin.  Stop being so uptight and being offended so easily. If he says something that gives you pause, brush past it. If he keeps trying to force the conversation a certain way, then leave if it makes you uncomfortable. But at least see it through, if only so you can better learn how to handle such situations.

Every date is more practice for the next one. People should go into every date wanting to enjoy themselves and be good company. Where we go wrong is expecting our date to impress or wow us and forgetting that they are expecting the same in return.

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49 Responses to “This Is How To Get Past The First Date”

  1. Carlos Says:

    These are pretty solid pointers. Starting interesting conversation on online dating sites has been challenging for me (though much less so since I started a few years back), since a lot of the profiles I look at are very, very similar and it’s often hard to not converse about the usual boring stuff (school, job, blah blah blah). In these situations,

    Starting conversation is easy for me when the person’s profile has an interesting picture, something fun/funny in their profile or something I can relate to. It’s hard for me to talk about something other than the family, friends, and requests for “someone fun and exciting” that I see on a lot of profiles I’ve come across. When I’ve tried to make conversation with people who put these types of profiles together (some people aren’t great at putting their true character on paper) with something generic and funny (hopefully), at best we’ll exchange a few messages before it starts to get boring for me. I feel like I’m the one trying to be “dynamic” in those situations, but I could be the boring sap you make mention of. :)

  2. Eliza Says:

    Again, you get nasty, and outright judgmental, why? Because someone has shared their perspective on not wanting to drink. You need to lose your miserable attitude…let alone those 25 extra lbs! You preach about learning to make conversation…yet you come across like some bull in a china shop. Very abrasive, judgmental and condescending.

    • John Says:

      Eliza…..I dont think its so terrible you dont want to drink on dates. My question to you would be if you communicated that to the guys in question? Because if you never told a guy you dont like to do drinking dates how else would he know? I suggest those types of dates simply because its customary to do so. But if a girl said she didnt like that, then I would gladly offer to do coffee/tea and dessert at a nice cafe. But if she didnt mention this fact and quietly stewed about it, then that wouldn’t be fair.

      If on the other hand, you expressed this concern and they still forged ahead with the drinks idea then you have every right to be frustrated. But dont let Moxie make you feel you are uptight or abnormal because you dont like to drink on dates. There are guys out there that have no issue with that. My gym and rollerblading friends drink very little simply because alcohol plays havoc with your workout the next morning. Males and females. There is a group of 15 of us that rollerblade many Sunday mornings together. When we stretch prior to the skate we invariably talk about what we did that weekend. Many times it just consisted of going to the movies or going to dinner followed by an early night. We joke how boring we are. Yet we still do this lifestyle because it makes us happy. And this is a 50-50 split between male and female with all but one being single or divorced.The fitness crowd has a good pool of singles who dont drink a lot. I know many ladies that run 5ks and lift weights and are turned off by guys that drink. You aren’t alone in that regard.

    • Selena Says:


      There are many people who don’t like to drink. They are not all in recovery or “health nuts”. Some don’t like the taste. Or the effect of even small amounts. Or the calories. Or they feel it’s a waste of money. They don’t find it necessary to be judgemental about others who drink socially though. Or resentful if someone asks them to go for a drink who doesn’t know them.

      • Trouble Says:

        If you don’t drink, don’t make a big deal about it…just order a coke or something, and if people ask you why say, “oh, I don’t really like the taste of alcohol, but I love a coke.” It’s not whether you actually drink or not, it’s about not being uptight if other people do.

        I often meet friends for drinks, have one beer, and then drink water or soda the rest of the night. I don’t like to drink and drive, and I also don’t like to get intoxicated very often. No one ever seems to mind, but then, I don’t make a big deal about other people drinking, etc.

      • wishing u well Says:

        Agreed. I’m not a drinker, by choice, no other reason. Alcohol just underwhelms me. But instead of making an inadvertent crusade of my dry status, I just opt for something else. If asked, I always say, “None for me, thanks, but go ahead.” In group settings with mostly drinkers, I found that sometimes they are uncomfortable with my choice. My little trick to rectify that is to order a ginger ale. It looks as if it may be an alcoholic beverage, and no one’s the wiser, lol. The key is to continue to be comfortable in your life choice without making others feel uncomfortable in the process.

        • Saj Says:

          I never would drink on dates (could easily cite the religion reasons though I don’t follow those to the letter) and wouldn’t really get a lot of issues with that. I’d prove my lack of interest by sipping their beer and making a scrounged up gag face and declaring how it tastes like a foot.

          Now I’m a wine fiend and get more teasing for that then from every single date where I declined to drink combined. I honestly wouldn’t worry about that. It seems like strange peer pressure. Come on all the cool kids are drinking! Feh to that.

          Ignore the non drink shaming!

          • wishing u well Says:

            “I’d prove my lack of interest by sipping their beer and making a scrounged up gag face and declaring how it tastes like a foot.”

            You know, the only way that I’d do that is if I were sure that the guy in question would know that I was teasing him and wouldn’t be offended. Otherwise, yup, definitely up my alley as I do a lot ot teasing of my own, lol. But no worries – I’m pretty laid back but those who know me well know that even though I do so quietly – I stand firm in my decisions once I make them.

    • Andthatswhyyouresingle Says:

      I wasn’t being nasty at all. You don’t like to drink? Okay. Don’t drink. But why does that have to spin into how society is so fixated on alcohol? Why do you have to judge the guys that like to drink? Why can’t you just shrug it off? Why does it have to be about the misguidedness of everybody else?

      You need to lose your miserable attitude…let alone those 25 extra lbs!

      Yet, despite this alleged miserable attitude and alleged 25 pounds I (don’t) need to lose, I still get asked out a lot and go on dates and have relationships. You, on the other hand, do nothing but complain and gripe about how pretty much every man you meet isn’t up to snuff. You’re the one who comes here every day and yammers on about how everybody else has it wrong and how baffled you are by how other people – people who actually date and seem happy with their lives – think differently than you. But what you never share are the stories of the enjoyable dates or series of dates you’ve been on. Because of that, I can only conclude that you don’t have a ton of luck meeting men, and I have to wonder if maybe your attitude plays a part in that.

      • A to the F Says:

        I don’t date or trust anyone who doesn’t drink. Drinking is a part of having a social life. I can’t share my life with a teetotaler. Plus they get all judgmental. Someone who doesn’t drink has serious issues, be they emotional, mental or spiritual. And I don’t need that.

    • wishing u well Says:

      Eliza – that comment you slid in regarding Moxie’s weight wasn’t judgmental? What does that even have to do with the current thread? Let’s dial it back a bit and discuss.

      First of all – congrats to you. It must be hard to have a family member in recovery without choosing to go down that road yourself. That is a small victory, and I can understand if being dry is a more serious life choice for you than perhaps others. I can almost relate. My grandfather passed away years before I was born due to the longterm effects of alcoholism, and the impact was and is still being felt on members of my family. Therefore even though I myself do not have that personal direct link, I’ve seen the effects that it can have.

      I date with a similar mindset as at this point (preference for a man who does not drink or lightly drinks) as my goals are long term. I know that if a man I were to date does drink, I’d like him to be free to do so, and I’d like to see how he handles it, how much, whether it’s a crutch, etc. And I’ve never made a big deal about this. Once you make your own decision for you internally, no need to preach about it. Just pay attention. If asked, be honest about your life choice, but just relax and pay attention. Ideally you’d like a man that you are interested in to feel comfortable enough to be himself around you, yes? If so, you will have your answers soon enough. But relax, which was part of the overall gist of the post. I think that you took personal offense to Moxie’s comment and miseed the whole point. Lasering in on things like this without putting them into their proper perspective completely takes the joy and fun out of the dating process. And you aren’t being your best self if you aren’t enjoying yourself….so please – step back. Breathe. And look at some of the great suggestions made. Anyhow, I wish you well.

      • wishing u well Says:

        Oh and one other thing: keep in mind that part of the nature of the dating process means that we will date a LOT of people who aren’t the best fit for us. There’s no magical way to avoid this or cut this out of the process, though a lot have tried. So be confident in yourself and your life choices, but relax. So what if you go on a 1st or 2nd date and the guy drinks like a fish? Wish him well, and continue to meet new people! It’s fairly simple, really….the more you make a big deal of an issue, the more likely you are to attract it to you. So please….calm down. And as always, I wish you well.

        • Saj Says:

          Lol come on wishing that quote in the main post was such a non subtle dig. It’s like putting on the boxing gloves and going I dare you to go a round. If that wasn’t baiting I don’t know what is.

          • Andthatswhyyouresingle Says:

            Actually, it wasn’t. It was a quote that inspired part of the post.

            I’ve ignored you and your drunken ramblings because you’re obviously quite a mess and have little else to do with your life but comment on blogs. But I’m happy to block you again. The only reason you were unblocked is because people find your idiocy entertaining.

            • DrivingMeNutes Says:

              Free Saj.

              PS. I agree with virtually everything in Moxie’s original post. I’m impressed that Moxie was even able to generate controversy on this one.

              If you don’t drink, you are less fun (to many) and you will be handicapping yourself relative to others who do drink. Really, you keep kosher? Oh, you’re a vegan? God says you can’t have sex? Same. My view is that life presents enough challenges over which you have no control, that you should maximize your attractiveness in the areas you do control. So, drink up.

              • Andthatswhyyouresingle Says:

                Exactly. Jesus. It’s one drink. Sally sip it. Stop being such a stick in the mud about EVERYTHING. Stop coming up with non-existent reasons to bail on someone and just face up to the fact that you’re probably just an insufferable bore or insecure.

          • wishing u well Says:

            I actually don’t think that it was a dig at all, looking at the overall context of the post and the points made. To me – looking at the big picture is key. Now clearly, Moxie is not adverse to a drink, and there are a lot of people who aren’t. So were I Eliza, I’d gloss right over that point in particular (as we know the alcohol ain’t happening, lol) and look at the REST of the statement – becoming more accommodating or only dating men who don’t drink.

            To me – I think that one can become more accommodating without breaking down and drinking. I know this to be true because I choose not to drink, and I see both sides of the coin. This conflict isn’t new to me in the least. The key is to be graceful, enjoy the date, and let the guy know afterwards if asked that you don’t feel the connection needed to move forward. Nice, easy, respectful, and part of the dating world. Heck, half the time we women don’t know “why didn’t he call us back” as men do a variation of this themselves. Why can’t we also do it, but with class?

            • Selena Says:

              The thing that struck me in Eliza’s comment, was that she seemed to disaprove of someone else having a drink. A little resentful that men would ask her out for drinks on date 1,2,3. And: “And if you don’t drink with them? Some men don’t find it enjoyable.”
              Maybe they don’t find it enjoyable because that get the message from her she disaproves?

              And the part about society being fixated on social drinking? It would make me reluctant to take her to a party or other gathering where I know there would be drinking, thinking she would be uncomfortable. Perhaps make my friends uncomfortable for having a good time with alcohol included.

              Absolutely nothing wrong with not drinking. Making other people feel uncomfortable about it though doesn’t make you come across as fun and easy going.

              • DrivingMeNutes Says:

                I don’t disagree that one shouldn’t make your date feel uncomfortable. But, there’s more here. The point, I think, is that even if you are non-judgmental, you are still less “fun” on a typical date than someone who drinks. That doesn’t mean I think anyone should drink to be more fun or to please me. I won’t “judge” anyone for not drinking either – that’s your business. I’m just not going to date you.

                • Jada Says:

                  DMN, you won’t date a non-drinker!? Oh damn it all to hell, I was just about the ask you out since we seem to agree on so much in the comments, but if you’re going to be so narrow minded and judgemental about my teetotaling you can forget it.

              • wishing u well Says:

                Exactly, Selena, I picked up on that as well, and that was what I was addressing.

                And DMN, I’m known to have just as much fun as the next one and could out party quite a few people, if motivated enough. For me – I tried it and all it does is exaggerate my personality. I’m outgoing, very energetic, and generally happy. It just kicks that WAY into overdrive…and why bother when I like myself just as is? Nope, but I love the fun involved. Back in my mortgage industry days, pre-housing bubble burst, I was well known to socialize at many a happy hour and have a good time….and so did the others around me. And the daily happy hours at the Hilton were legendary in the area at the time….we had so much fun that people’s spouses / significant others knew that there was a good chance that “working late” was a brief stop at the happy hour. Good times! I like being around people and positivity and sometimes alcohol brings that out in others. Nothing wrong with that.

                • DrivingMeNutes Says:

                  I’m fun when I’m sober too but I like to drink on dates because the date is more fun. You want to share in an activity you both enjoy. If I loved basketball and my date doesn’t care for it, I wouldn’t want to make a date at a basketball game. Even if she’s otherwise a blast-and-a-half, if she doesn’t like basketball, that basketball date’s probably going to suck.
                  Or relatively so.

                  For me, a drinks date IS a fun date. That’s why I’m not a good match for someone who doesn’t drink. She may be fun, but the date won’t be. The question then is: are more people like me, or not like me. From what Eliza says, more people are like me.

                  • wishing u well Says:

                    It depends on how flexible and willing to compromise the other person is. My ex was hugely into video games. Me? I can take them or leave them. But I developed a knowledge about them and lightly played them with him – and he seemed to appreciate it. So this is why I don’t really address the non-drinking thing….I make it a non issue and encourage the guy to enjoy himself. As long as he isn’t a loud, sloppy drunk, we’re good.

                    If the woman doesn’t like basketball but is very much into you – I’m willing to bet that she’d develop at least a working knowledge of the sport. And for me – I just choose not to drink, but I don’t have a problem with it. If I change my mind, I change my mind. Besides, someone has to be the designated driver.

                    • DrivingMeNutes Says:

                      I need to revise my commentary on this subject because it occurred to me that, not too long ago, I actually dated someone for some time who rarely had a drink. I remember this woman of course, but I had completely forgotted that she didn’t drink.

                      It did matter. Setting up our first date was excruciating, and it’s a miracle we ever actually met. I suggested drinks (as is my way) and she countered with BRUNCH on a SATURDAY. UGH. I told her I don’t “do lunch dates” and I don’t “do coffee dates” and I prefer drinks in the evening. We lost touch. Then weeks went by and for whatever reason I decided to make an exception and we ended up having a brunch date (I drank bloody maries, she didn’t drink.) I assumed she was alcoholic, but turned out she was avoiding drinking for diet purposes, so she said. Go figure. Once in the relationship, it didn’t matter much as WishingYouWell suggests – mattered so little I completely forgot.

                      Anyway, here’s my revised point. It’s not about being fun or not, or refusing to date people who don’t drink. It’s about maximizing your dating opportunities. As I said above, everybody has handicaps (some literally) that they cannot change or fix, and that will present challenges in terms of dating or makiing relationships. Those you need to deal with. To the extent you can avoid creating unnecessary handicaps for yourself, you should. Tying yourself to restrictions about what you can eat, drink, say – will limit your dating options. It’s just about recognizing that fact, I think.

                      Oh, and I wish you well.

    • Jada Says:

      On the interwebs you know someone is losing an argument when they resort to correcting your grammar or spelling rather than address the topic at hand. And you know someone is an insufferable miserable twat when they resort to calling you fat or ugly rather than staying on the topic at hand.

      Looks like we have another insufferable miserable twat in the comments. And no, I don’t mean me.

    • chillybeans Says:

      0uch Eliza, I think I would need a cocktail just to begin to tolerate your attitude!

      It’s all in the attitude, and yours is so defensive. My ex husband didn’t drink, and neither did a boyfriend I dated for two years. Neither one of them minded my occasional cocktail or wine with dinner, they never lectured or preached.
      I thought it was awesome, because I had a built in designated driver!!! And you save on the check, when you go out, since alcohol is always increases your tab.
      See, it’s all in how you present it:)

  3. K Says:

    Agree with most everything in this post. I online dated for about 6 months last year, and briefly this year, and am off the market at the moment. I didn’t go on a million first dates, but the ones I did go on, with one exception where we clearly couldn’t stand each other, always resulted in a request for 2nd date. Here was my M.O.:

    1) First, make sure my profile “sounded like me” but without any red flags. I had a couple of people take a look at it and they suggested a few tweaks or told me to get rid of something here and there. For example, I was leading with a paragraph about how I like to try new things, go to parties and dancing, etc. My guy friend thought I was coming across too much like a “party girl” so suggested I move that down and move up another paragraph about what I’m looking for in a relationship. He also told me to get rid of “I’m neat and organized,” because no one needs to hear that. I also had something in there about my financial stability but eventually axed that because we can get to that eventually, doesn’t belong in my profile. I never had any demanding laundry list of qualities I’m looking for, either. Never mentioned anything negative in my profile, or “don’t be like this,” etc.

    2) Have recent, accurate pictures without other people in them, with one or two that show more of my body

    3) Go through the emails and winks I received from guys and see which ones I actually have some potential interest in, and wink back or send a quick email to get things going. Exchange 2-3 light and breezy emails and if they didn’t suggest getting together for a drink, just stop responding. Emails were usually concerning what we like to do for fun, recent trips (guys tend to ask about that), or something interesting we noticed in each other’s profile. I would never suggest we talk on the phone. If they really wanted to, I would, but would keep it brief.

    4) Meet for drink. I live in the Boston area and there are plenty of casual yet unique places to meet for a drink. Usually sit at the bar which I think makes it easier to talk. I would always go into it with the attitude that I’d meet someone new and have an interesting conversation. I never put too much pressure on it, like “omg, this might be the one” or “I have to find out everything about him” or “make sure he meets all the points on my list” (I don’t have a list).

    I would wear a pretty dress, or nice jeans and top, touch up my makeup after work, curl my hair, etc. Look nicer than “Work nice,” but not “Saturday Night nice.” And then just chat with the guy like he’s a normal person. NOT like an interview. Let him do more of the talking, see what he wants to talk about. Answer his questions without TMI. First date is not the time to mention that I spent 8 years in a dysfunctional relationship with the wrong guy. Be myself, laugh a lot. If he wants to eat, eat something. Go for my purse when the check comes but let him pay. I always had enough cash to cover the whole thing if need be, but most guys insist on picking it up, which is fine.

    5) The guy would usually send a text or email after the date saying he had a good time and would like to do it again. If I liked him, I would respond and say I had fun too, sounds good. If I liked him but *didn’t* hear from him right away, I’d probably send a text / email saying I had fun.

    That’s it – it was really pretty low-stress. I’m a business person and not a kid anymore, and can have a nice convo for an hour or so with most anyone… but I did enough filtering of profiles and emails that I almost never found myself on a date with someone I found difficult to talk to. Again, never put a lot of pressure on anything or treated it like a job interview. I do tend to laugh a lot, and get a lot of “I like your laugh” type comments. I try to put people at ease, but also stay somewhat reserved – not get wasted, not touch people much / at all on a first meeting, not get into negative topics or reveal too much. Just be interested in what they’re saying and ask questions to keep the conversation going.

    Anyway, that’s what worked for me. If I do it again, I may be more proactive about reaching out to guys whose profiles are interesting. But the method above again consistently resulted in 2nd, 3rd, 4th dates, and eventually what seems to be a healthy progressive relationship so far.

    • Joey Giraud Says:

      What a real post, you sound almost too sensible to be here.

      But: “Let him do more of the talking,” would, to me, seem a bit suspicious. Do you really men who will happily chatter away while you sit and listen?

      • K Says:

        Nah, I just don’t want to feel, after the date, that it was all about me and I didn’t let him say what he wanted to say or learn anything about him. There’s plenty of time for me to run my mouth later on. I haven’t really found myself on a date with someone more quiet / shy, probably because I filter and can tell a lot from emails, but if I did I would definitely do more talking, ask more questions to draw him out. I don’t just sit there quietly, but I also think you can learn a lot from what a person chooses to say / talk about on a first meeting, and I don’t want to miss it. I also think it works in my favor if I’m just a little hard to read / don’t lay it all out on the table, you know?

    • LostSailor Says:

      K, that’s the approach I’ve developed, and it’s working better this year than last. I’ve relaxed and am having fun. Spring and Summer last year were pretty fallow times, but I’ve been busier than ever lately, date-wise.

      Let him do more of the talking, see what he wants to talk about. Answer his questions without TMI

      Uh, I don’t think we’d have a good date. Because that’s what I do, ask questions and let her do more of the talking and answer questions without TMI. We’d end up staring at each other, waiting for the other one to talk while an excellent bottle of French Chardonnay gradually warmed to room temperature…

    • Andthatswhyyouresingle Says:

      but I did enough filtering of profiles and emails that I almost never found myself on a date with someone I found difficult to talk to.

      This is the key. People make the mistake of accepting a date with anybody interested. When I go out, I know I’m going to enjoy myself. I like getting ready for a date almost as much as the date itself. Make the whole experience fun.

      I think ti was Jada who once said she never went on a date in pants and it’s so true. Putting yourself in the mindset of being girly and flirty starts with what you wear.

      This is a perfect strategy for a good first date. It all starts with your profile, too. My guy friends took a look at mine and said that it made me sound like someone they’d enjoy hanging out with. That’s what your profile needs to say.

      • Jada Says:

        I never went on a first date in pants, and rarely wore them in the early stages of dating. It’s funny you mention this, because by a weird coincidence I recently became friends with a girl who is the BFF of a guy I briefly dated years ago. She told me I was known to her as “the girl who wore a dress to the Cubs game.” It was a casual sundress, but apparently it really stood out in a sea of t-shirts and shorts and that was exactly what I was going for at the time.

        If you don’t want to go out with a heavy drinker, don’t agree to go to a bar on your first date. Just be sure to suggest an alternative, “I was thinking we could get coffee at my favorite shop and then go for a walk along the lake front,” (my former go to date suggestion) or for night time dates, “the museum of contemporary arts has cool events on Friday nights, we could check it out.” Yeah, you’re going to have a smaller pool of dates to draw from if you want a non-drinker, but that’s just what it is because most people do drink.

        I don’t drink anymore but I still like bars and parties and strip clubs, all places normally associated with conspicuous alcohol consumption. I personally don’t mind being around drinking and in ways think its even funnier to be sober when everyone else is getting ripped. And I’ve noticed, no one really cares that I don’t drink. I don’t make excuses for it, I don’t really offer up reasons, I just order club soda with lime and have a good time. And because it looks like a vodka tonic or gin and tonic, lots of people don’t even realize I’m not drinking. It probably helps that I don’t act like I have a giant stick up my ass.

  4. K Says:

    Here’s something else though. While I had “success” last year in dating as defined by good first dates leading to 2nd dates etc., I didn’t find a guy I truly clicked with or, more importantly, a relationship, until a major shift occurred in my thinking.

    First I’ll say, I don’t have any obvious major barriers like drama, entanglement with an ex, weight, financial problems, anger, or “messiness” going on. So in many ways last year I was free and ready to date. (I think if you have issues like that, you may kind of have to deal with them first.)

    However, it wasn’t long after a breakup from a bad, very long-term relationship, and I think I was kind of “dating scared.” To some extent I took in messages about the difficulties in dating as a female over 35, was a bit afraid and freaked out by being alone, but worst of all I don’t think I believed that a truly healthy, supportive, progressive, and *fun* relationship was even possible or something I’d be able to find.

    Anyway, I spent a year getting myself together after my breakup – I took trips, went out, had fun, treated myself really well, and most importantly realized I was totally ok on my own. I truly came to accept that I was fine just as me, by myself, and let go of these fears about being alone and having bad prospects as a late 30s woman. By the time I went back online again, I was really at peace. And then pretty much right away I found someone awesome.

    This probably sounds really cliched, but it absolutely was my experience. When that feeling of peace and self-acceptance came, it actually brought tears to my eyes, and I knew I’d be ok. For me it was a religious experience, but I don’t think it has to be for everyone. You just have to know and really believe that you’re ok and that you can find a relationship that’s truly good for you.

    • Trouble Says:

      Anyway, I spent a year getting myself together after my breakup – I took trips, went out, had fun, treated myself really well, and most importantly realized I was totally ok on my own. I truly came to accept that I was fine just as me, by myself, and let go of these fears about being alone and having bad prospects as a late 30s woman. By the time I went back online again, I was really at peace. And then pretty much right away I found someone awesome.

      This was my experience, as well.

      One other thing I would add: dating, to me, is really kind of like an interviewing process for a prospective boyfriend (and hopefully someday, longterm partner or husband). Not every candidate is going to be a good fit for a job (and you aren’t always going to be a good fit for them). Don’t take it personally. Just move on and keep a smile on your face.

  5. offensivedan Says:

    I appreciate the posts and insight from K. However, online dating is a woman’s game. They have all the power—even the average ones. It is exponentially easier for a woman to find someone than a man. So, nowadays, I don’t have a gameplan other then getting laid as quickly as possible. That’s my advice to the male gender deciding to online date. You need to think of a first or second date as the last time you will see this chick, so you can’t delay trying to get laid. If she gets offended, who cares, as you wouldn’t have seen her again, otherwise.

    • Trouble Says:

      I thought women in our 40s were all desperate sad losers who couldn’t compete with women in their 20s and 30s and were doomed to a lonely life of cat-herding?

      I think you people should pick a story and stick to it.

      • Selena Says:

        Ha! :)

        Depending on the fellow writing – any woman over 35 has lost ‘value’.

        Hard to believe women have such a short shelf life when so many guys are unable to get laid.

        • Joey Giraud Says:

          Guys who go on about sexual market value and junk like that are losers, no doubt.

          But older women don’t have the raw sex appeal a younger woman does.

          OTOH, an older woman has the potential to totally out-charm the 20 something girls.

        • offensivedan Says:

          Even if a woman is in her mid to late thirties, if she is cute and in great shape, her value will not go down. In fact, her value will go up if she is open to dating younger guys as she will meet their requirements of being attractive and older. Take a look at the profiles of these types of women on–it’s not coincidence that they will goa s youn as 30-31 years old even if they are 38 years old or close to 40 years old. It’s obvious they can still attract younger men.

      • LostSailor Says:

        Trouble, not all women in their 40s are sad losers with a herd of cats. Thankfully for me. But if you’re single and you have more than one, you might want to think it through…

    • K Says:

      Offensivedan, you might be right, I don’t know. I’ve seen a lot of comments from guys on this site and others stating they believe that women get “hundreds” of messages, or tons of messages a day, and can just pick and choose. I’m not sure about that. I can only speak to my own experience, but I got a few emails and/or winks per day (after the initial week or two). There were days when I got nothing. Maybe younger women get lots more messages? I’m mid- to late-30s, but I’m also (I believe) above-average in attractiveness and can honestly check “slender” on Match. And like I said, I don’t think there are any red flags in my profile.

      I do think it may be harder for guys though… You likely have to do more work. I will definitely let the guys do the first contact and the asking on dates. If I go on a couple dates with a guy I like and then don’t hear from him for a while, I *might* reach out and tell him I’d like to see him again, but in my experience if he’s not asking, he’s probably either not interested or has something else going on.

      So yeah, I would say it may be less work for women. But if I like a guy, I do encourage him and let him know I like him / enjoy his company, and I do seriously offer to pay for dates. I also will let a guy know I appreciate what he does for me. I’m definitely grateful that guys are willing to do the work!

      PS – sure, can’t blame a guy for trying to get laid on the first or second date. I get it.

  6. A to the F Says:

    There’s some solid advice in this column for women.

    Sundress it up. YES! Even if you look hot in designer jeans, trust me, you look hotter in a sundress.

    And yes, don’t be so judgmental. Too many women are looking to be offended, and come off as stuffy or with a stick up their ass. The most fun I’ve had (conversationally) is with women who roll with the punches and throw right back. I push the envelope, its fun and its a good way to find out what kind of person is sitting across from you. If you get all prissy, well, now I know why you’re single. If you’re sassy right back, cute and funny in the volley, even if you’re a little shocked, well that is super hot.

  7. erine Says:

    This is nonsense that if you are a non-drinker you won’t be as attractive and “fun” in a man’s eyes.
    I don’t drink at all. Have never had (ever in my life) a full serving of beer or hard liquor. On occasion, can make myself take a few sips of wine but never the entire glass (or, actually, half of the glass that is typically considered a glass of wine). If anything men have acted amused (in a good way) and intrigues by my non-drinking in a sense that it was a novelty for them. If I went on a date to a bar, I would sometimes get a glass of wine and only take a sip or two or I would just get water with lemon (I don’t like soda or artificial “juices” you typically find at a bar). Never had a problem with it.
    Never had a problem with men having a couple of drinks either. You either suggest that you two meet at a cafe for coffee/tea or if not, go to the bar but order juice or soda or whatever non-alcoholic drink you want and don’t make a fuzz out of it.
    DMN said he wouldn’t date someone like that but most likely he would happily drink a complete non-drinker as long as he was attracted to her and find her interesting. I don’t think a lot of men or women prioritize their potential partner’s drinking habits when considering going out with them, nor does those habits influence the production of those magical chemicals in your body that are responsible for those rare instances of immediate attraction. I’ve gone out with men who really liked to drink when they were out and were happy to split expensive bottles with me (and pay for them), some of them even tried nicely to persuade me to drink a little (that was past our first intimacy so they didn’t do it “to get laid”) but I just didn’t like it, and they were as interested in going out with me as they were before they found out about my non-drinking.
    What I do agree with that most likely the problem for Eliza is her attitude. If you say something playfully a man would adore you, but if you say the same thing with a stern tonality and with negative connotation, the man is going to see you as rigid and – UNFEMININE. Most things you do or don’t do in a FEMININE way will be found charming by a man who is initially attracted to you.

    Also: K might have been successful with online dates but then she said she “didn’t truly click” with those men. Well, unfortunately, if you wait for that perfect click you might end up alone. You better look at the men who think you two CLICK and pick the best one out of the group. The time for magical butterflies and magical connection (which, almost always, is a code for animal attraction) is gone.

    All this is coming from the woman who got married less than a year after first meeting her husband. We’re celebrating the first anniversary of out meeting this Friday by the way.

    • Saj Says:

      I don’t know about this FEMININE thing despite it being mentioned over and over. I also got married around a year after meeting despite my aversion to dresses, my competitive nature when playing games together and not being into getting tipsy in public.

      Acting playful and cute I get. Little things you can do (though if it’s something you practice you may come off a bit strange). Such as getting really excited when talking about something, being passionate about your hobbies, cute tics and mannerisms. But I guess if he really likes you then lots of random things he may find cute.

      A random thing I’ve seen is that men really dig if you have some artistic skill say like singing or playing an instrument. I never thought it was anything important but when we went to a piano store on a lark and I started playing something on one of the models and he had no clue I could do that and was impressed. Now one of his favorite things to do when I’m playing on our home piano (that he got for me soon after) is to listen to me play even though I’m not terribly good at it. Other male friends who didn’t know and found out also seemed more impressed with it then I thought they would.

  8. erine Says:

    Also looking at the single women I know I realize that a lot of times, their not very successful dating life is explained by the fact that they forget about FEMININITY.
    A lot of women are just so interested in women’s rights, in their independence, blah-blah-blah, that they forget that nice makeup and a dress and, most importantly, an ability to be charming and feminine during a conversation are the things what most men find attractive.

    • Joey Giraud Says:

      Yeah, I know the attitude: wearing a nice dress is allowing yourself to be objectified. Being charming is giving in to the patriarchal expectations of a sexist society. Being demure is asking to be exploited.

      “Modern women need to be strong, independent, and “… makes Jill an unhappy conformist.

      There has to be a middle ground here.

      • Trouble Says:

        I think it’s a definitional issue. Strong/independent =/= rabid bitch. A lot of women mistake asshole for strength and imitate the conduct of the worst of the men they know. But, the strongest men I’ve known were also some great family guys who loved their wives and kids, would share what they know and would always help someone else out. Men don’t like male assholes, either, so why would they like female ones?

        You can be charming and feminine and still be strong and independent. In fact, your strength will probably get a lot more mileage if you are also charming and gracious.

  9. Mark Says:

    A guy wrote a message to you. You probably looked at his photo, were interested, and looked at his profile. You were still interested and wrote back.

    That led to a conversation. You said a 10 min. talk. Then you say from his end interest dwindled.

    Well….OK That happens.

    Be honest. I’m sure that there were men who contacted you, or maybe you went on an initial conversation over the phone, or even a first date and you knew relatively quickly that things were not going any place with the guy. You either let him know this or stopped communicating with him. It doesn’t matter why, you simply decided that It served no purpose to continue. At any one of these points you either broke off contact or said/ did what this guy did.

    That seems to be the case here. You seemed interested, but after a little contact he decided (for whatever reason) you would not be right for him. Sorry to be blunt, but that’s simply the way things work.

    So now you have to stand tall, move ahead, or decide on someone else.

    Hope things improve.

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