Updates: “That Girl” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today, we hear from “That Girl” who developed a crush on a new booty call and then felt crushed when he stopped hanging out with her. “Should I just wait for him to ask me to hang out again and move on if he doesn’t, or should I try asking him out one more time?” she asked. Keep reading to see where things stand now.

Wow. When I look back at the letter that I wrote to you and your response and the reader comments, I’m so embarrassed! What was I thinking! Of course, that’s what you were going to tell me. That’s what I was trying to tell myself, but I let myself get all crazy and wrapped up in the situation. Why is it so easy to do that? Why is it so easy to forget common sense when you have a crush on someone?? The one thing you said that really hit me that I’d never thought about before was that just because he didn’t want to date me doesn’t necessarily mean he wasn’t into me. Yea, this guy could totally smell my desperation.

Anyway, once I had sufficiently embarrassed myself with this guy, I gave up on him. I failed to mention in my original letter that this bar that I “frequent” is actually literally connected to my office, as in, one of the entrances to my office is through the bar. So avoiding the bar was not exactly an option. But I’ve kept interactions with him to a minimum and always keep them friendly. Well, a couple of weeks ago, I went on vacation and was gone for over a week. Since I’ve been back, it’s like he’s done a 180. He’s the first to come up to me whenever I enter the bar, he came and found my office the other day just to say hello, and yesterday he came to my office again to ask me to dinner.

Now I know I’ve heard it a million times, and I’ve even told many friends who needed to hear it before, but it still baffles me that, the minute I stop showing interest in a guy, he comes running! I turned him down for dinner because I was actually busy, but I would like to hang out with him again. I will, however, keep it friendly for now. After all, it did effectively take him a whole month to call me back….red flag?

And no, readers, I will not be sleeping with him again any time soon! For the record, two dates is pretty much my average for sleeping with someone. Yes, that seems really quick, but it’s just the way I work, and it has generally worked for me (most of the time!) thus far. I’ve had multiple satisfying, long-term relationships that included sex on the second date, so at the time sleeping with this guy so soon did not seem like such a mistake. But who knows where things will go from here. At any rate, thank you Wendy and readers for smacking some common sense into me!

Don’t beat yourself up too much. Also: let this guy work for you a little bit. He’ll value you more for it.


If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at [email protected] with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].


  1. This is a nice update, but I really, really, really, really, really hate gameplaying. This guy sounds like he’s playing games with you — his 180. The people that do this stuff, I think, don’t necessarily realize what they’re doing so he’s probably not a bad guy. I hope he realizes that good, strong relationships aren’t based on drama, tears, and silent treatment. Yeah they can get boring, but they’re stable, open, and healthy.

    I’d take Wendy’s advice, but beware. People who pull this nonsense are into the chase not you. They’re constantly looking for the next thing, and it’s pretty sad.

    1. I think I am in a benefit of the doubt mood today but honestly, I don’t know if it is games so much as only appreciating things when they are no longer there. Like when you lose power. You don’t appreciate it until it is out.

      1. I don’t get it. If he didn’t want her at the start, why does it have to take her disappearing to get his attention? I think that just means he never really wanted her in the first place.

        If it really did take losing her FOR A WEEK, then he’s the wrong guy. You’re supposed to appreciate what you have when you have it not when it’s gone.

      2. have you ever heard the expression, you don’t know what you had until it’s gone? i don’t think he’s the first guy or girl to start appreciating what he had until it went away. and he probably won’t be the last.

        not that i think that makes him or his actions ok, but he’s not unique in his actions.

      3. It makes no sense, but I swear guys do this. The minute you stop paying attention to them, they start coming after you. Playing hard to get does work. I think it’s because the minute you have to work for something, it becomes more valuable. He still may turn out to be a dud, but at least now he knows he needs to step up his game.

  2. Dude sounds like maybe good booty-call, FWB, casual sex material, but possibly not boyfriend material. I wouldn’t say you shouldn’t keep seeing him or go on dates or whatever, but I wouldn’t expect this to turn serious anytime soon, nor would I go into it expecting that it will lead to a relationship.

    If what you’re looking for is a relationship, then maybe this guy’s not worth your time; but if you’re open to having some fun and letting things happen organically and not worrying about the potential for a future, hey, go ahead, have fun.

    And never apologize for your personal timetable for sex! That’s so up to you and no one should make you feel like 2nd date is too soon if that’s not what you feel yourself.

  3. This guy’s interest has probably ratcheted up due to some “wants what he can’t have” thing. A lot of people are like this at times, but if you (the general “you”)find yourself wanting something just because it’s seemingly unavailable, then you never REALLY wanted it in the first place.

    But anyway, yes–it’s very common & I’m not at all surprised that this guy is sniffing around you again. I’d keep things casual. Also, did someone make you feel bad about sleeping with him after the 2nd date?? Don’t worry about it! Like KKZ said, everybody’s timeline for that sort of thing is different.

  4. I agree with the other commenters – but I would like to add one thing – don’t put all of your eggs in one basket! Why are you focusing all of your time and attention on this guy? Surely there are other men that you could be talking to/going out with! If this guy is really interested in you, he will be interested in you if you are not “always available”. And I agree that it sounds like he is playing games….

  5. landygirl says:

    Here is an analogy…I have friends with children. My friends children will ignore them all day but the minute they get on the phone with me all of a sudden they want their parents undivided attention and will bug, whine, and ask questions until they get off the phone not because they actually need something, they just want what they can’t have. This happens even if both parents are in the house…they want the attention of the one who isn’t giving it to them.

    This guy is no different.

  6. what office do you work at where one of the entrances leads to a bar? i’d be more than happy to work there!

  7. Avatar photo bittergaymark says:

    This seems like less of an update and more of a continuation…

    1. pumpkinbread says:

      i had the same thoughts.

      it started off with all the makings of That Girl learning THAT lesson…but then it trailed into the same kind of rationalizations and flimsy boundaries that got the LW, and me (and countless others) in this same kind of situation.

      it took me almost a year of sleeping with a guy (who’s “bed” was a mattress on the floor). YES! A MATTRESS-ON-THE-FLOOR and he was 29 years old!!!!!! before i “got it.”

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