Guy Advice

You asked a dude, and he answered


Dear Isaac,

I bequeath to you my greatest relationship quandary to date (lucky guy). I met a guy through Glimpse (Insta dating). He contacted me and we hit it off. We went on a great first date, he asked me to a second. We saw a thoroughly depressing movie and chased it with a bit of bar time — too much bar time. We fooled around, I stayed over. I left feeling like an idiot. Isn’t it cardinal rule # 1 that you wait until date # 3 to take off some clothes? Seemingly for good reason, as all hilarious texting on his end became one-word answers.

I finally told him that I thought I blew it and asked if he’d be up to hang out again. He agreed, and the date was awesome. We kicked back with some beer and our favorite video games and held a good conversation and flirtatious tone. He offered to let me stay over instead of catching a very late train home. I was happy to end it all on a good note/demonstrate that I was not a crazy person.

As good as it was, he’s been pretty silent. I never offered a “Hey, that was fun! Let’s do it again” generic response. (Should I have?!) Where do I go from here? Is the ball now in his court? Or is it sadly deflated and being scooped into the recycling bin?

Love and Basketball

Hey L & B-ball,

It honestly doesn’t matter if you’d waited until the third date, the 100th date or forever to have sex with this guy. The results would have been the same. Sex is clearly an important aspect of a relationship, but it doesn’t change anything in a scenario like this.

Here’s the deal: A guy has made the decision that he will have sex with you — if it’s offered — the moment he asks you out. It is that black and white. He hasn’t necessarily made the decision that he’s interested in pursuing a relationship with you, or that he might want to see you again afterwards, but he has decided that if you are keen on sex, then he is too. If all goes well and he feels a connection, then of course he’ll want to keep things going, but he has to feel a connection.

You guys hung out once, it was fun. You hung out a second time, drank too much, then fooled around. He didn’t contact you much afterwards, which suggests to me that he wasn’t particularly interested in continuing to get to know you. I’m sorry if that sounds harsh; I’m sure you’re an amazing person, but he might not have felt the same connection that you felt. It happens.

What you did next was probably not your strongest move: You got back into contact with the guy who hadn’t been forthcoming with attention, told him you thought you’d blown it, and asked for another chance, effectively giving him all the power and then some. He said, “Sure,” you guys hung out again, and of course he offered to let you stay over — not because he’s a gentleman, but because he thought there might be another opportunity to have sex.

If he’d wanted to keep things going, he would have. He didn’t. The ball is no longer in the court, the ball is gone. To be honest, the ball is most likely back on the dating app attempting to hook up with other women.

Don’t ask him out again — trust me when I tell you that you’re way too cool to have to pursue somebody who won’t make a little effort in return. And don’t feel like an idiot for hooking up with him. But if you’re going to feel that way if a similar scenario arises in the future, maybe wait till you’re sure that both of you are looking for the same thing before you jump into the sex.

Hey Isaac,

My boyfriend and I have an incredible relationship, to the point where I have to pinch myself. Still together after 4 years, still best friends, fight so rarely that I don’t think it’s even happened in a year, and still very much in love. Now the kicker. Said boyfriend and I had both began the relationship knowing marriage wasn’t an interest of ours, but we had spoken very rarely in a “maybe us someday” way in regards to children, never delving too deep into it out of…whatever reason. fear? staying present? who knows. He recently moved 2 hours away and it’s forced the hard talks we’ve put off and he’s decided apologetically that he definitely doesn’t want to have children, but still wants a life together. This is a huge deal breaker as i’ve always seen myself as a mother.

Is this a normal defense mechanism of men? I’m wondering if this is ever a conversation between men…I don’t want to convince someone to be a father and he said he may “down the line” be open to it, but is that just a line to make me feel better?


Bringing Up Baby

Hey …Baby.

That is quite the conundrum. Sounds like everything is perfect between you two except for that one little thing; the problem being that this one little thing is kind of the be-all end-all of your relationship.

Nobody likes talking about the serious stuff early on. Kids and marriage and lifelong commitment and prenups are hardly sexy or conducive to a romantic dinner conversation. But you guys have been together four years, you’re best friends, you’re in love and you don’t fight. Surely you must have had endless opportunities over the last, say, two or three years to bring up future plans?

But since you didn’t, now you’re faced with a crazy dilemma, and you have two unpleasant options: 1. Give him an ultimatum that he changes his mind or you end the relationship; or 2. Stay with him knowing that you’re never going to have kids together. There are only three possible outcomes in that scenario, and two of them sound pretty heartbreaking to me (breaking up or staying together without kids).

Sure, he might change his mind at some point down the track, but what if he doesn’t? What if you’re always hoping and he’s always pushing things further and further back? Sounds like a oneway ticket to Resentmentville, population: one.

For the record I don’t think this is a normal defense mechanism for men, as far as I can tell, the average guy wants to have kids. I think this is a very specific situation, and it needs to be addressed sooner rather than later. I think it’s time to have some frank conversations about the future of your relationship.

Have a question for Isaac? Post your questions below or email with ASK ISAAC in the subject line. Follow him on Instagram here, Twitter here, and check out his website here.

Get more Postmodern Love ?
  • MT

    Dear LW2: When I met the man who is now my husband, I assumed that one day I would want kids. As our relationship progressed, quite happily, I assumed that one day I would be all about it. That never happened. As time passed, I realized that I am not a mother, at heart, and don’t want to be. About three years after we got married, it occurred to me that, though we’d stopped talking about hypothetical future children, it was unfair to have made this decision for myself without having had a proper conversation with him, but I was terrified, because understood one thing beyond all doubt: If he wanted kids, at all, I would have to leave him, because I refuse to be the thing that robbed him of being a father if that was a thing he wanted in life, and I know with every fiber of my being he would never ever leave me. So it would have to be me, and that terrified me, because I fucking love this dude more than I can accurately describe, and leaving him would very possibly ruin me.

    Now. It sounds like your dude is great in many ways, but what he’s not great at is ripping off the fucking bandaid. My guess is he knows full well that you want to be a mother and that he cannot be the thing that stands between you and motherhood. It’s cruel to be that thing. So what irks me is that he did not do this math before telling you he didn’t want kids, and understanding that he can’t be your partner in life and not want kids. Those things are mutually exclusive, and rather than say “I don’t want kids” and lead you down this shitty road of wondering what the fuck to do about it, he should have said “We have different goals in life, and now that we’re apart most of the time I realize I’ve been selfish in staying in a relationship with you, and we need to break up.”

    What I’m getting at is that under no circumstances should you give him a fucking ultimatum. What you should do, is thank him for his (belated) honesty, tell him you love him, but that you have different goals in life and he’s standing in the way of yours.

    Because if he’s using your desire to be a mother as a fucking tactic to get you to dump him, he can go fuck himself, and if he legitimately has just made the decision that he does not want kids and it’s a firm enough decision to share with the partner he knows wants kids, then it’s not a decision, it’s just a matter of action that one of you needs to take. He hasn’t, so you need to.

    (My story ends well: husband never has cared much one way or another about having kids, and when I said Nope he said Okie dokie we’ll just be the cool aunt and uncle. And we are.)

    • Amelia Diamond

      Hey! Wow! Thank you for this comment! Can I ask you my dating questions too??

      • MT

        LOL sure, if you want! My experience is limited, but that’s never stopped me before.

    • Wow, Monica could have really used you as a friend when she broke up with Richard in season 2. You seem like a very cool aunt.

      • MT

        Sometimes situations are really, really simple, and things like love make the simplicity really fucking hard to see. Which is totally normal and I have a lot of empathy for it, but it makes me super useful as the Friend Who Will Tell You What’s What Without The Bullshit.

    • Aubrey Green

      Can I have your email to email you a question?

      • MT

        My email is my name, which I avoid putting on disqus. Thankfully I can have as many gmail accounts as I want, so I made a new one:

        Have at it! ManRepeller, feel free to give me a column. 😉

  • jenn

    Dear Isaac,
    Within the past 6 months, this guy would randomly pop into my life to ask me to grab a drink. Once I agree, he chooses a day and then I never hear from him again, not even to explain what happened. WHY? He’s done this at least 6x and only committed once (the first time). The rest of the time he literally vanishes and pops back up a month later to ask to grab a drink, and the cycle continues. He has flirted insanely with me and has even attempted to booty call me. I’m so confused how he could pretend to be interested (even in just hanging out) in order to not follow through. What gives? Not sure if it makes any difference that we work for the same company, but I rarely ever see him. Although the potential chance keeps me from calling him out and making things awkward. I know he’s going to come back texting me in a few weeks to grab a drink too. What’s a polite way to say, “get your shit together”?

  • Lauren

    That first response hits way too close to home. Thanks for having me all in my feelings so early in the morning, Man Repeller 🙁

    • Amelia Diamond

      here is a virtual hold!!! *{———-o————}* or a starwars ship, idk. sorry.

  • SChase

    Isaac, at what point is the ball ever in the girl’s court, so to speak? Seems like once she decides to hook up/have sex it immediately jumps from neutral to his court unless she holds out, which isn’t what she wants either. So it’s hook up and lose the dude most likely, or hold out for some made up reason. Are decent guys that hard to come by?

  • I’m not in a relationship right now but this was all fascinating to read. Both the column itself and the discussion below.

  • Greer


  • “Here’s the deal: A guy has made the decision that he will have sex with you — if it’s offered — the moment he asks you out.”

    That reminds me – my boyfriend of over three years once told me that he didn’t know if he wanted to on our first date.

    I really like Issac’s response to the first question. I’ve heard from enough guys (friends or stuff like podcasts) that if they’re into you, they’ll actively pursue you. And I don’t think a guy that’s too scared or shy to ask you on a date would make a very good boyfriend.

  • rgee

    Love the response to the first post! If a man is interested in you, even if he doesn’t know if he wants a straight up relationship, but just interested in you because you’re amazing- he will make a point to find himself with you in a hang out/date situation. He will reach out and persue you. That’s how you start to feel special by that person and real feelings may magnify. A guy being shy is a seemingly cute trait, but then you have to play the game of guessing what he feels or means. That’s too much work…it shouldn’t be that complicated. If he likes you he’ll just have to Nut Up, that’s my ramble about the “is he into me” convo.

  • merci

    nice post !
    blazer wanita

  • angelique

    Ive been talking to this guy for 3 months. I finally did it with him, and he text me thought i wasnt speaaking, i hit him back, no response. what do i do?

  • Zsen

    I met someone for the first date. He acted interested before,during and after date. He said that he is busy with his work, and he hasn’t asked me to go on the second date. He also said during the date that he is a little shy. I don’t want to rush and get into a relationship with him, but I do like to get to know this person better. I like to know him or see him only if he is interested in me as well. The two things that makes me think that he might not be interested is him not asking me for the second date, and also after the first date he never initiated texting me. He does answer texts and shows interest on conversations. How to know for sure if he is interested or not? Also because he said that he is a little shy makes it hard for me to know. What do you think?