Successful Online Dating Requires Some Hard & Fast Rules

Name: Nancy
State: NY
Age: 38
Comment: While doing online dating, I’m running into the type of man who sends lots of engaging emails, but doesn’t want to meet in real life.  After email 5 or 6 I suggest we continue the conversation over coffee or drinks, but they either dissappear, or arrange a date then cancel or don’t confirm.

I’ve also had a few first dates, where the man has kept in contact after the first date via SMS or email, telling me how much he misses me etc, then arranges a second date but doesn’t confirm.  They usually come sneaking back without apology after six weeks, but by then I’ve already moved on.

Another type of man I’m encountering is the one who wants daily phonecalls and no dates.  Coincidentally, they have all been IT professionals who don’t have a rich social life, but enjoy hearing about mine.

Ignoring the men who send emails like “your hot” “wanna f**k”, I’d say a quarter of the serious emails I’m getting are from men who want to meet after swapping about 3 or 4 mails.  Three quarters are from men who appear to want a virtual girlfriend.

Funnily, when I realise that the emails and phonecalls aren’t going anywhere, I mention to them that I went out on a date with someone, then they disappear.  I know its taboo to mention other dates, but by email number ten to twelve I’ve reached a level of frustration that I no longer care.

Do you think that I’m handing things wrong, or putting them off in some way?  Or am I just too impatient with these men?

I thought that maybe my profile attracts the loner types, as I have a wide range of hobbies and some of them might pique their interests, e.g. science fiction.  I’m currently rewriting my profile to make myself sound more sociable and outgoing, and working on getting photos of myself at social events, so I’m attracting more outdoorsy men. I’m also going to scour my profile to make sure there are no nerdy references.

Can you and your readers suggest what else I may be doing wrong?


I’ve also had a few first dates, where the man has kept in contact after the first date via SMS or email, telling me how much he misses me etc, then arranges a second date but doesn’t confirm.  They usually come sneaking back without apology after six weeks, but by then I’ve already moved on.

I think what’s happening with you is that you’re frequently being placed on the back burner while these guys explore other options. They’re keeping their options open by continuing to engage you, but they’re out there dating other people. They don’t want totally cut you off, just in case. As I said in a recent and similar post, they’re playing their odds at your expense. Practically everybody deals with this at one time or another. (See this other new post about how to handle this particular situation.) At any given time we’re all communicating with multiple people. That’s why it’s important to get offline as soon as possible. It’s way too easy to fall between the cracks and get lost.

This is the nature of online dating and you can’t take it personally. But you can learn to spot these guys before you waste too much time.

Once more for the cheap seats……….

If they don’t confirm a date after exchanging 2 or 3 emails, take the initiative and ask them out. If they don’t commit to anything within 24 hours, move on. If he or she wants to speak on the phone once the date is set to make sure you’re not a serial killer or too boring for their oh so engaging personality, give ‘em a call if you’re really that interested. But in general this is a gross waste of time. 3 emails. Set up date. Confirm day of. Meet. No chitty chat in between. Ladies, send the thank you text after the date and say you’d like to do it again. Guys, if you’re interested, take that and run with it and set up another date. Fin. The End. That’s dating today.

Another type of man I’m encountering is the one who wants daily phonecalls and no dates.  Coincidentally, they have all been IT professionals who don’t have a rich social life, but enjoy hearing about mine.

This is another common sub-section of online dater. They’re just looking for someone to pay attention to to them or are too afraid to meet someone off line and “ruin the magic.” They like the idea of seeming perfect.This happens a lot, especially if people are using old photos of themselves and they know they no longer look like those pics. Or they’ve just been blown off so many times that they are afraid to take the risk. Whatever the reason, the most likely outcome if you did meet was that you’d be disappointed.That’s why these people need to be cut off pronto.

I do agree that your science fiction related interests or hobbies is going to draw these men to you. You don’t have to take those references out. What you can state in your profile is that you do not IM or text or email with anyone off site until a date has been set. You should also say that you prefer to exchange no more than 2 or 3 emails before meeting. Most men are thrilled by this and are happy to comply.

I said this last week. These people who need all these steps and all this time to work up the nerve to ask you out or to confirm plans are time wasters. So sorry, folks. They either are very cautious or skeptical or they are using the site for attention/entertainment purposes. Or they are horrifically social awkward and you’ll have to coddle them. You need to stop making excuses for these people. It’s not your job to help them through whatever awkward phase they might be going through, nor are you potentially losing out at The One by being quicker to dismiss bad behavior.

The only thing you’re doing wrong is engaging these guys. You need to take a hard and fast line when it comes to how much time and energy you are willing to devote to them. The longer you stay invested in these dead end situations, the more frustrated you will grow and the more people you could be meeting are meeting someone else. This is why so many people get burnt out and go on “dating detoxes.” (Which, btw, are a total sham. They’re not going on any detox. They just want you to think they are so you will, too. Misery loves company.)

Think of this approach as sort of a Cleanse. You’ll be getting rid of the toxic people more regularly to make room for the healthier ones. Over time, it gets easier and you’ll have a greater sense of control over the process.

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32 Responses to “Successful Online Dating Requires Some Hard & Fast Rules”

  1. L. Says:

    Unbelievable. And many men I know encounter the very same thing from women who just don’t appear to be very serious about dating. They linger on these dating sites and we wonder if they actually ever go on dates.

    Chances are, there’s nothing that you are doing wrong or nothing that you can change. It is just a general degradation in society these days and sense of entitlement … especially on the internet … where people feel that they don’t owe you (or anyone else) the simple and common courtesies that used to go along with how people treat human beings.

    So enough of the why. My advice is first of all, just keep trying. You will eventually find men that are serious-minded, although it may be difficult. Secondly, most women I know won’t allow it to go beyond three email exchanges. If he hasn’t asked for your number by then, either just find a polite way to tell him that you’re moving on, or if you really like him … send him your number and tell him you don’t like to email incessantly and like to progress it to the phone at this point. Thirdly, don’t fall into the trap of these experiences causing you to make generalizations about guys in certain categories. Just keep trying and try not to become prejudiced if you find a lot of these types of guys in certain age groups, who don’t live in certain neighborhoods, who have certain careers, who are from certain backgrounds, etc.

    Lastly, try to ensure that you are not attracting the type of men who are jerks or who will waste your time. I don’t think there’s anything in your profile that is likely to do so, I think it’s more once you start emailing with them. Make your emails nice … but short and to the point. Don’t encourage their going on and on an on and if they seem like they are bantering too much or going off on tangents… bring them back on topic. There will be plenty of time to have long discussions when you meet.

    When my friends and I engage someone on an internet dating site, we generally write emails each with 2-3 paragraphs trying to get to know someone just a little bit better each time, we always ask at least one question (usually pertaining to her profile on the first email but probably relating to the last email on the subsequent emails), and we generally ask for a number on the 2nd, 3rd, or in rare cases, 4th email. Every time. I don’t think you should tolerate anything less.

    Good luck.

  2. Andthatswhyyouresingle Says:

    2 to 3 paragraphs??? That’s way too long. 3 sentences max. Multi paragraph emails make you look like you’re trying too hard.

  3. Ed Says:

    One of the problems with online dating is a lot of people care too much what other people think instead of being themselves. I’m not worried about looking like I’m trying too hard. I do what I want. I’m also guilty of everything Nancy complained about and work in IT. Hell, who knows? Maybe I even met her online or in the real world at some point. I never stand anyone up though. I admit there have been times when I canceled the day of, and I’m not proud of that because I know it sucks and wouldn’t want it done to me, but by that point I had lingering doubts and the thought of suffering through another mediocre date as opposed to something more productive like a good workout was just too much. Bottom line: I just wasn’t that into her. Maybe also, I met someone I was more interested in since our last communication. I realize it’s all bad and makes me look like an asshole, but I’m not into wasting my time or anyone else’s. I’m also not looking for a meaningless hookup. Been there, done that. Also, there is the possibility of miscommunication. Maybe the guy is just trying to save himself some dates by basically getting it done over the phone or by emails. Whatever the case may be, isn’t it better than meeting, starting something, possibly getting physical, then disappearing? I’m not saying it’s right, but it could be worse. Moxie is right, though: Everyone needs to set some rules for themselves when dealing with people online, otherwise it could be a huge waste of time.

    • L. Says:

      Actually, my feeling is … once you are in communication with someone, you SHOULD follow through with it … no matter what. No matter what kind of “lingering doubts” you have. Do you REALLY expect to be going on a first date with a complete stranger (especially one that you met over the internet) and NOT have doubts? People have doubts about dates all the time. The purpose of going on a date is to get to know someone to see if those doubts disappear or reduce once you meet them. To do anything else (IMHO and with all due respect) demonstrates ambivalance about the dating process.

      This is another human being that you have begun to communicate with and it’s common courtesy to follow-through. If you still have doubts after meeting her, then you are well within your rights to NOT see her again. But at least you have her a chance. The only other reasonable option that I see is if the doubts are THAT serious and have been brought on by something in the emails or phone convo, then writing her to tell her that you’ve had 2nd thoughts MIGHT be ok.

      That’s the problem with society today. Everyone’s afraid about wasting their time or the other person’s time. Why would you assume that one date is going to turn into a “meaningless hookup”? These all boil down to rationalizations for not treating people right.

      Guess what? My modus operandi is completely different and you know where I work? In I/T.

  4. uesider Says:

    Pretty good advice. My belief is that online dating is mostly a waste of time so always approach it with extra time and never get at all invested.

    When I find someone I’m interested who reciprocates my emails etc, I ask her out within 2 messages. If they fade, I move on. For men in particular, it’s a numbers game. Most women (and I guess most men) are online for entertainment, validation, everything except meeting a partner. Chasing flakes isn’t worth your time.

    Another possibility is that you’re responding to the wrong kinds of men- it could be you’re being approached by shy, socially awkward men due to your hobby choice. Could also be that you’re overshooting your mark, responding/writing to men who aren’t that interested. A man who is interested and confident will make a date quickly because they want to meet you. If they don’t, they just aren’t that into you.

  5. Jaclyn Says:

    I had one of these “relationships” with a guy who wrote lengthy emails and never asked me out. His emails were interesting, so I kept writing back. After a week, I stopped expecting him to ever ask me out since there was nothing even flirty in his writing and just focused my energy on the guys who were writing a few times, then asking me out. Eventually, I started a relationship and told my pen pal that I wasn’t sure we should keep communicating since it just seemed a little weird. If a guy doesn’t ask you out within a reasonable amount of time, you should just take him out of the “potential date” box in your head. If you enjoy writing to him, continue doing so, but if he is annoying you or disappointing you, you should just cut him off.

  6. Rebecca Says:

    I’m on the back burner right now with someone I saw for 3 dates and had sex with. He sends cheerful, “warm” one-sentence messages every 3 or 4 days but is “very busy” and hasn’t suggested getting together again. I kind of want to tell him to take a hike, but our time together was enjoyable. I guess I’m keeping him on the back burner too as I continue to talk to other guys. I suppose this is what dating in these times looks like. It completely lacks romance, and is kind of depressing.

  7. Andrew Says:

    Your approach seems fine. What you might consider
    doing is if a guy asks for your phone # in the 3rd or 4th
    email, give him the number, but suggest meeting up anyway.
    Use the # to confirm the date & time. If he’s serious and
    has some self confidence, he’ll go for it. A phone call isn’t necessarily
    a bad thing,but I’d he doesn’t ask you out in that first phone call, move
    on. You’ve got better things to do with your time. Anyone who insists
    on constant emailing, or worse, constant IMing is also not worth wasting time
    with either.

  8. cyberian_huskey Says:

    I am pretty techie and artsy and not very outgoing, but I decided once I get out of college, there is noway I am going to do online dating! I’m engaging in my own life, and they will have to keep pace with me! I find the biggest problem is that men like to put everything in it’s own box. In other words, for guys everything stays in Vegas if he’s in Vegas, school if it’s school, work if it’s work, church if it’s church, home if it’s home. I’ve come to a conclusion that they do this so that they can live multiple lives and have nothing interfere with each other. So it’s like he’s a sailor with a girl in each “port”! I think that if I sense any little bit of boundary drawing, and resistance to integrate me into other areas of his life, then he’s not looking for a wife, he’s looking for a secretary, or a school chum, or a church friend or a bed mate or a…whatever restrictive label. So, these guys want virtual girlfriends eh? the thing is, they keep things restricted from each other for a reason. If they never want to meet you in life, that’s because of something. You don’t know what, but normally it’s something they have to hide. for example, a wife, girlfriend(s) etc…and yes some guys like ego rushes and attention, but there again, that is also something that could happen if they are taken or seeing others. And guys also are lazy. and often cheap too. Lazy is a big one though. If they can get attention and whatnot from you online, and not need to get up off the chair to buy you a measly coffee, that’s just laziness. Men are also camels….they don’t need much female interaction. Just when they want it, and then all the other times, they are working, playing video games, doing whatever they do, or sometimes getting excited about new female prospects…they don’t see a need if you are there at a convenience behind a screen. If you want to meet men in live, you have to meet them in live. that’s what I am seeing.

  9. hb Says:

    I married the guy who I exchanged one email and then met for coffee soon afterwards (on a whim and rather spontaneously, expecting nothing, since I was getting online burn out at the time and did not want to email a lot either) and still we are happy as clams four years later. I didn’t need to text him…he followed up right away with an email and a call for another date. If a guy is interested, you’ll know. He won’t be playing games. He also respects your boundaries at the same time being receptive to your cues that you’re into him.

  10. Jeannie Says:

    Question: what is it- when a guy asks for your number online, he will call, not leave a message . Then writes a message online stating he’s been trying to call me . Since when is a hang up call a legit phone call?

    (And by the way, this is after 2 weeks of texts back and forth and I finally asked him out. He then took this detour of” the phone number/ call lost in space”. ) This has also happened to me twice with guys in “real time”. The hang up call as their first call. Please tell me this is not the new way of dating when a guy leaves a hangup call and then that’s supposed to spur me to call??

    I guess this is 2 questions. One, cut the online guy loose? Two- the hang up call is the new phone call?

    • The D-man Says:

      I rarely check voice mail. I went cell-only last year. I figure if someone wants to reach me they can text me. I prefer text for message like “This is Bob, give me a call back at XXX”

      • Elaine Says:

        Contrariwise… I can touch-type, but hate texting on the tiny keyboard of a phone. Also, I’ve found that some guys use texting for weasel moves like canceling a date the day of (really? you couldn’t call for that?), or for sending awkward sexy talk which I think they think are compliments (really, please do *not* compliment any body parts whatsoever with someone you’ve never met in person!). So I just tell everyone I’m old school (which I guess is a euphemism for old) and please don’t text, and then if they do send a text, I don’t acknowledge its receipt. IMO texting is only for very brief messages during times when you’re not supposed to be on the phone.

    • Phoenix Ember Says:

      Yes, it’s common these days for cellphone users not to deal with voicemails at all. Retrieving them burns up minutes and the message rarely communicates anything more than that the person called—which the phone keeps track of anyway.

      I’m curious: Why, if you’re interested in this guy, are you not taking his calls? I’ve noticed women _never_ answer the first time a guy calls. Why is this?

      • Jeannie Says:

        Thanks for your feedback , this is good information RE: the hangup call not really being one. Before we got to this point, I did ask him out via email to set up a date , time, etc over a week ago. This was after email back and forth for 2 weeks. He then sort of took the detour into this phone zone and is kind of staying there.

        • Andthatswhyyouresingle Says:

          Is there any reason why you haven’t just called him back? Isn’t the call on the caller id enough to let you know he called?

          I doubt his decision not to leave a voicemail had to do with burning up minutes. More likely he felt.awkward leaving a voicemail. Take that as a huge red flag. That’s a sign of serious social awkwardness.

          It seems like you have deal with this sort.of situation frequently..the guy contacts you and you just do nothing while you waitfor him to do what you think is the appropriate action. While you wait and analyze his intentionws instead of just replying to the guy and meeting. That’s part of why this is going on for twoweeks.

          • Phoenix Ember Says:

            More likely he felt.awkward leaving a voicemail. Take that as a huge red flag. That’s a sign of serious social awkwardness.

            Is there a reason to be jumping to this conclusion? Really, I don’t know a single person under about 35 who leaves voicemails anymore. Like, ever. Voicemail died among the younger generation once we gave up on landlines and had to count our cell-phone minutes carefully. Nowadays people more often have unlimited airtime but the habit has stuck. Voicemail is basically a 35-and-up technology now.

            So there’s a perfectly reasonable explanation for this guy’s behaviour that doesn’t involve him suffering from a crippling personality disorder or being a social predator. We’re not all losers, Moxie.

            I agree with you, though, the real question is why Jeannie refuses to either answer this guy’s calls or call him back. This behaviour seems to be common and I still don’t understand it. Jeannie?

            • Crotch Rocket Says:

              My no-vmail “habit” didn’t come from counting minutes; it comes from the fact I spend hours at a time on the phone for work; if someone leaves me a vmail, all I get is an annoying little icon until I’m off the phone–at which point I start returning all my missed calls anyway. Depending on the hour, though, they may not get a call back until that night (personal) or the next day (work), when they’re probably busy themselves and can’t answer. This is where “phone tag” comes from. OTOH, I can read texts and emails (and reply to them) immediately.

              Most vmails are worthless anyway; most just say “This is Bob; blah blah blah blah; call me at 123-456-7890″, i.e. the same information I already had on my caller ID. “Checking” my vmail now means deleting the messages unheard so the annoying icon will go away.

              FWIW, I don’t leave vmails for other people either; if they don’t answer, I text or email. This seems to be the norm for Gen Y and younger, in my experience.

            • L. Says:

              I think that leaving or not leaving a voice-mail is up to the individual. I also find it kind of ridiculous that an entire generation dismisses voicemails. There are times when it’s simply the right thing to do and makes total sense. Planning a date, for example … after it’s been agreed to … leaving the time, restaurant, address … or arranging for when/where to pick the person up.

              But that is NOT the issue here. The issue is … why is someone … ANYONE … making assumptions about this person just because he didn’t leave a voice-mail? Social awkwardness? You don’t even know him for gosh sakes!!!!! Suppose he got an emergency call while your voice-mail greeting was playing? Suppose he had a heart attack? Suppose someone screamed “Fire” in his office? Suppose … just suppose … that his preference is not to leave a voice-mail for a reason that you cannot possibly anticipate or understand!

              Why … why oh why … are people so damned judgemental in dating and so eager to jump to negative conclusions about someone that they don’t even know? This happens over and over here and in many other examples that I have seen. What is everyone so afraid of? Taking a risk on someone? So you won’t see him again! OMG people!

              No wonder so many people have trouble finding Mr. or Ms. Right! You’re elminating half the world before you even get to know anything about them!

              • UESider Says:

                So right- making ridiculous judgements about people we haven’t even met yet. How childish. Everyone is different, everyone has their quirks, but it just seems like some people here see every little oddity as a signal to disqualify someone.

                And then the next post is someone whining about how it’s so hard to find someone decent. Geez. It’s like people want to be alone.

              • Andthatswhyyouresingle Says:

                Why … why oh why … are people so damned judgemental in dating and so eager to jump to negative conclusions about someone that they don’t even know?

                Because we’re human. You’re trying to create some sort of uprising against this behavior and you’re wasting your time. You’re trying to get people to be less judgmental and give people a second look and look beneath the surface. All nice things, but totally unrealistic.

                Few people are going to give up their time or money to meet someone who doesn’t interest them just because it’s the altruistic thing to do. Oh, and because you wish they would.

                • L. Says:

                  No, I’m not trying to change anything or create any kind of uprising. I’m commenting on what is obvious ridiculousness, and what any dating expert, coach, or psychologist would say is underlying fear and/or ambivalence. Rationalization is NOT “being human”. Having an open mind and striving to be non-judgemental is NOT being altruistic. It’s being reasonable, it’s being fair to yourself, and it opens up doors and possibilities that can lead to achieving goals and to your happiness. Worst case scenario, you don’t see the person again. Big deal!

                  And I don’t know where you got the impression that I was suggesting that people meet someone who doesn’t interest them. I said no such thing. You are putting words in my mouth. I wouldn’t do that, and neither should you or anyone else.

                  You are absolutely right that I can’t change the world. But YOU have options as to what you can do. You can take my comments and rationalize them (as you seem to want to, Moxie … which with all due respect … I personally feel sets a poor example for your readers). Or you can maybe think about them. And your readers can do the same.

                  Making enough of a negative pre-judgement about someone that you don’t even know because that person chose not to leave a voice-mail message is not only ridiculous … it’s selling YOU short. To NOT make that judgement has nothing to do with altruism and at that point, you (or anyone else) couldn’t possibly have the foggiest notion of whether that person interests them or not.

                  But … if you relish the thought that you just may have given Mr. Right his walking papers, suit yourself.

        • Andthatswhyyouresingle Says:

          Also, what’s the difference in how he let you know that he tried to call you? The voicemail and the email saying he called achieve the same thing. Why does it matter how he left the message?

          • jeannie Says:

            OK, I got my answer, and not so sure this needs to go on further without me sounding defensive. Bottom line.:
            1.2weeks of emails back and forth
            .2. I asked him out via email.
            3. He came back with can he talk to me to hear my “lovely voice”. first? OK, so we exchanged numbers.
            4. Meanwhile I am having doubts in the back of my mind because I am thinking the obtaining of phone number should be to set up arrangements for date , what i read on this blog. He texted once about when to call me. I texted back when
            5. He called and didn’t leave message around late afternoon , when I wasn’t going to be avail.
            6. I didn’t call back because honestly I truly didn’t think a hang up call was a phone call to answer back to. I have found out differently since reading this blog today. I know I am sounding ancient, but at 49 and having been married for 16 + years ( divrce final 6 years ago) online dating and the fast pace of it is all new to me. Online dating has even changed in the past 5 years when I first tried it out. I can’t answer Phoenix Ember’s question on why all women don’t answer their phones. In my case I truly just didn’t get the call / wasn’t looking for the call since it wasn’t within the timeframe I specified.
            7. So from now on , I have learned that hang up calls may mean many things. Back in the day it used to mean the least amount of effort to get a woman to call, however now I know better.

            • Andrew Says:

              If you’re interested in this guy, ask him out. If he gives you the runaround (won’t give a direct answer, dances aroundthe question) get out and find someone new.

              As for what most men are thinking when calling for a date (if we even do that anymore as emailing and texting seems to be taking the phones place), we view is a a bank robbery in that we want to get in (ask for the date, set up a time and place) and get out (end the phone call). I’d be wary of anyone who wants to spend too much time on the phone with a complete stranger.

              Bottom line…set up the meeting with the other person because that’s the only way you’re ever going to really know. If they don’t want to meet, don;t waste your time.

  11. Carina Says:

    OP, move on. If you wanna keep going with this I suggest calling him back and hang up after 1 or 2 rings. Same as he did, right?
    Remember the guy needs to pursue YOU! And thats that. Oh and I would never say thanks for the drinks, coffee or whatever. NEVER.
    The guy that is into you he will call you either way to ask you out again.

    • The Reluctant Monogamist Says:

      You NEVER thank someone for buying you coffee/drinks? That’s just plain rude, whether it’s a dating situation or just family/friends. Sending a quick “thanks” to someone after a date is not going to affect the outcome of them calling you back or not. It’s just a nice gesture.

    • Selena Says:

      Never say Thank you? Who on earth did you learn that from? I feel embarrassed for you just reading that.

  12. DrivingMeNutes Says:

    Never say “thank you?” Hm. Not sure I (or even my 6 year old niece would) agree with that strategy but its an interesting data point that we will someday hopefully use against you.

    Its true that certain guys will chase down a woman regardless of how rude she is or how she treats him. (Why would he do that, I wonder?). Presumably, you don’t want one of those guys do you? Well, you apparently do because your strategy detailed above along with lack of critical thinking skills screens out all potentially reasonable and decent suitors who weren’t raised in a barn. Except your boyfriend of course.

  13. M Says:

    I can understand the frustration with guys not wanting to move things offline. Have you tried to make anything happen? I would suggest you take the initiative and plan something rather than wait for them to do it, because it sounds like they arent up to the task. Having to wait 8-10+ emails for a date is ridiculous. Considering what these guys are like, they may be a little shy and nervous, so cut them some slack if you like them. If you try to move things offline and they balk or stall, then that would be a good time to cut bait.

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