Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

How Long Is Too Long?

This week’s was inspired by, well stolen from Starangel82. With her permission, of course. You can see the original here.

She’d met a man online and they’d been chatting and she quite liked him.  And was ready for him to ask her out.  More than ready. And it’s been her experience that men don’t like it when women do the asking (she lives in the South).  So as much as she wanted to hurry things along, she felt she was stuck.  Waiting.  For him to ask.

I’ve been in similar situations.  Well, somewhat similar.  I certainly don’t live in the South, and I’ve asked guys out plenty of times in my life.  But not men I meet online.  I tend to want them to do the asking.  To show me that they are actually interested in having an offline relationship. That they’re real. That they’re not just some bored guy who’s looking for a secret thrill when no one’s looking at the office, making up stories about himself.

So I have a pretty strict 2 week rule.  If I meet a guy online and he doesn’t step up within the first two weeks and at least suggest getting together then I assume it’s not going to happen and move on.  Sure there are exceptions.  People go out of town.  People get insanely busy for one reason or another.  But, in general, I give guys 2 weeks.  And then I move on.

BTW, Starangel wrote (I’m paraphrasing) that if you wait too long before a first date you get stuck in the friend zone. This has never once crossed my mind.  Not sure what to make of that.

What about you?  Do you have hard and fast about this stuff?

How Long Is Too Long

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25 to “How Long Is Too Long?”


  1. Jane Wonder says:

    It never occurred to me to think a man wasn’t real if he didn’t ask me out quickly enough. That’s an interesting take on it that I just never considered. I do think 1-2 weeks is a maximum though. Simply because if they don’t pony up with an invitation by then, usually it means (as much as I hate to be a cliche) he’s just not that into you. They will often continue to talk to you as a diversion, but a man who’s really interested is definitely going to step forward.

    Now, like I told Starangel82, I’ve been known to gently prod for the invitation if I think the situation may require that. But I learned quickly not to press or fish too hard. A gentle prod is enough to let a guy know you are interested if that was his hold up. And if it wasn’t, well, see the earlier cliche.

    • Simone Grant says:

      I guess I fold your “just not into me” into my “not real” in this context. A guy who keeps writing and saying he wants to meet, really likes me, wants to hear about my day, blah blah blah but never asks me out is in my mind “not real” which could also mean “just not that into me”. Or maybe recently divorced and not ready to date. Or maybe lying about who he is (really a 55 yr old security guard instead of 45 yr old project manager). In mind the why of those things never really matters :-)

  2. Izzy says:

    I have never joined Match.com, although I think about it frequently. However I have met people on Twitter that I became very friendly with. We would flirt, talk about similar interests, and then it got to the point that I would actually look forward to the “direct message” or “g-chat”.
    In this instance, I waited about a month or so.

    I would have to agree with Starangel – if you wait too long you’re risking getting stuck in the friend zone. IMO – if you don’t want this to happen, just back off. Don’t be as accessible after a certain amount of time. If they miss you, they’ll want to know what’s up.

    • Simone Grant says:

      This friend zone thing, I’ve never experienced it. I’ve actually gone from friend to more than friends. And from lovers to friends. But I’m just not “normal” I guess.

  3. Jolene says:

    I totally agree – it can’t fester too long before you actually meet. Beyond the friend zone issue (which I can see, but haven’t worried about), you can get too comfortable talking online and may say things you wouldn’t normally say to someone you hadn’t even met yet. I prefer a week tops, unless of course there is travel involved or busy schedules (that are legit, not just excuses!). my two cents :)

    • Simone Grant says:

      The comfort thing is a big issues for me. I think many people become too comfortable with people they meet online, before they meet. I’ve done it too. I think it creates a false sense of security.

    • DsGuide says:

      True indeed. These days people are so comfortable with the online thing for many reasons. For one, it’s easy escape for people looking for a more anonymous way to meet, especially cheaters. The internet is a great outlet for virtual fantasies.

  4. Starangel82 says:

    After some gentle prodding, he did ask me out. He was afraid I’d turn him down because he is in a wheelchair. An understandable fear, but there is still a point where you just have to bite the bullet and ask!

    I still believe 2 weeks is a good rule.

  5. Lila says:

    I think if a guy waits longer than 2 weeks to set a date and time to meet up, he’s just not that into you. I’ve never experienced online dating “per se” but I have made connections through social networking sites after meeting for the first time (usually through friends). From my personal experience the guys who are eager to get to know you better will not wait longer than one week (sometimes two if schedules clash) to set a date because they are excited to see you again. If he waits longer than that, he’s probably just playing the field or looking for time fillers. Never a good sign.

    • Simone Grant says:

      Yep. I actually like it best when a guy asks within the first few days (though sometimes that comes off as a let’s hook up suggestion). I’m always game for making an hour to meet for a late drink or a quick coffee.

  6. Miss Alpha says:

    Maximum of 6 incoming messages over a period of 2 weeks. :) No prodding. I don’t offer my number or call him or anything even if he sends the info. Recently a guy messaged me saying, “Here’s my email since my contract is up at the end of the month.” AFTER probably a 6 week delay where he was “out of town” aka “dating someone else that didn’t pan out.” LOL Oy… it’s simpler than people want to admit.

    • Simone Grant says:

      HOLY HECK, you’re more strict than me! Well good for you. I mean, I don’t see any harm in that. The truth is, it shouldn’t take that much negotiation.

  7. Jessica says:

    I’m one of the “it takes as long as it takes”, although really I think more than a month is a little too much. It took about a month for my now boyfriend and I to eventually meet up. And I was antsy after 3 weeks or so to meet him. But we were both new to the online dating world and I really hadn’t dated much at all, period! So it was a given that “this” was going to go slow. That’s why I said it takes as long as it takes. People are different…I’m shy and my boyfriend tends to be a worrier and a nervous nelly, that makes for a slow process. I do think though, after a month, you have to wonder how into the other person is (or vice versa)…if neither has the nerve or puts forth the effort, is it worth it? But let me also say, I’m REALLY glad I didn’t give up on my boyfriend after two weeks of chatting…I would have missed out!

    • Simone Grant says:

      Jessica,
      I’m glad it worked out for you. I always say that everyone is different and things work out the way they’re supposed to. You and your boyfriend are a good fit for one another, so the slow pace worked for both of you.

  8. pups4me says:

    As an online dater (off and on) for 5 years, I prefer meeting face to face sooner than later. I’m looking for dates/relationships, and at this point in my life (43) I don’t need an email buddy! When I first started online dating I discovered it was too easy to fall for someone over the internet and since chemistry is really important to me, I ended up being disappointed more often than not. I’m happy to suggest meeting for coffee or a drink if they guy I’m interested in doesn’t ask me first. My “rule” is the first time I meet someone it’s only for a drink or coffee–2 hrs. max, so if we don’t click it’s not that big of a deal.

    • Simone Grant says:

      You sound like my twin sister. Same here, except I’ve been doing the online dating thing for 10 years on and off.

      I just don’t see any point in developing feelings for someone until we’ve met. And that means meeting soon.

  9. Prep&Priss says:

    Totally agree – 1) men should do the asking, 2) it should happen quickly. Why else would they be online dating? Seems silly. Luckily haven’t met too many of these unreal types…

    http://prepandpriss.blogspot.com/

    • Simone Grant says:

      Well, lots of reasons “why” have already been mentioned in the comments (shy, a worrier, recently out of a relationship and not ready, a total liar) :-). Glad to hear you’ve been having good luck.

    • SFSingleGuy says:

      I often prefer it when women step up to the plate and ask, or at least give a strong hint. It can be difficult to tell when you’ve established enough comfort with a woman just over email; nothing as uncomfortable as asking her out, and realizing she sees you as ‘one of those duds’.

      That being said, I’ll usually make the move after 3 or 4 email exchanges. If she is still responding at that point, it’s a good indication she wants to meet up in person.

      • Simone Grant says:

        As always, it’s an area that has a potential for intense misunderstanding. Many women would be fine with hinting or asking. And others wouldn’t be. And some men wait for the hint because they don’t want to be rejected.

        UGH and UGH! If only we could just all read each others’ minds. Oh wait, that wouldn’t work either.

  10. 2 weeks is on the outside edge of my max, but it really depends on how much you’re exchanging emails with the guy. If it’s 2-3 times a day, then I’d expect an invite long before 2 weeks are up. If it’s only every other day or so, then I would wait longer.

    It’s not so much the “friend zone” that I’m worried about. For me, if I start exchanging emails and chatting with someone and I like them, I start to build them up in my head and can develop a really strong crush and very strong feelings before we’ve even met. I have learned the hard way that is a very bad idea to let that happen because then when you do meet, you want the chemistry to be there so badly that you’ll talk yourself into it even if it’s not there. That can only end badly. I’d prefer to meet in person quickly before I get much of a chance to get attached to the idea of a person.

    • Simone Grant says:

      Yep, that’s that false sense of security/intimacy I was talking about. It’s funny how some people are afraid of getting trapped in the friend zone and others are afraid of developing feelings for someone they might not have chemistry with. Funny.

  11. Starangel82 says:

    And our results are totally different… how very, very interesting.

    • Simone Grant says:

      Yes. And I wouldn’t be that surprised if these continue to change. Sometimes I would notice that the results of my polls would change – 4 or 5 weeks later the % would be completely different as more/different people voted.