"2nd-ish" Date Dilemma

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This topic contains 28 replies, has 1 voice, and was last updated by  peggy 7 months, 4 weeks ago.

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  • #713645 Reply


    I’m going on a 2nd-ish date this weekend. The reason I call it an “ish” date is because I met this guy twice through a mutual friend before our “first” date, and both times we spent a good amount of time talking to each other and hanging out.. definitely felt very comfortable with him. Which, in turn, led me to asking him if he wanted to be my +1 to a wedding (the “first date”), because I figured we would definitely have fun together. And we totally did! He made quite an effort to be able to come as my date, even though he had to be up early for important work meetings the next day, and he was an A+ date as far as being engaging with all my friends and having a great time. The wedding was a little far, so I did have a hotel room booked for myself back when I thought it was going to be just me. I had not intended to sleep with the guy but one thing led to another. And I have to say, it felt very natural. I wasn’t regretful of it afterward. He made multiple mentions of us going out again, and I believed him. About 5 days after the wedding he reached out to plan our next date, which is going to be a fun activity he had mentioned at the wedding. The thing is, the place we would go to is in the city near where he lives, and I’m about an hour away. I don’t mind it, considering he traveled so far and went so out of his way to come and be my (fabulous) date to the wedding, but it is a nighttime date, and we want to do drinks. I had mentioned that an earlier time might work better so that I could have time to sober up before I drive home, and he said I would be more than welcome to stay at his place, or we could stay with our mutual friend in the city. I realize we sort of blurred the lines with what happened at the wedding, so it’s hard for me to decide whether the idea of staying the night after this date is too fast/inappropriate. On one hand, we’ve gone out several times together, so it’s not exactly the traditional dating trajectory. But I also don’t want to move too fast. What are people’s thoughts on this?

    #713648 Reply


    You already slept with him and spent the night together at the wedding, right? So what is the difference if you stay at his place now?

    #713647 Reply


    My immediate thought is that trying to backtrack never seems to work. You’ve already crossed that line. Trying to go back to not having sex and being “appropriate”…I’m not sure it will work or if there’s a point.

    I think at this point it makes more sense to do what feels natural with him than to try to force things into a traditional mold or the way you normally do things.

    #713650 Reply


    Ali – Yes, and it would be much easier to just keep going with that flow for sure. I guess I just don’t want to give off the impression that I’m just looking for a f*ck-buddy. Although he isn’t acting like someone who’s looking for that, I suppose.
    Anon- Agreed, which is why I’m feeling a little unsure what to do. I feel like it would make things too strained to try and walk it back, but, as I mentioned to Ali above, I also am not really interested in anything casual at this point. Just don’t want to give the wrong impression.

    #713651 Reply


    Have you mentioned you are not really in a place where you are looking for a “casual” or “FWB” situation? That you are not in a rush, but are looking to get to know someone and really connect and hopefully lead to relationship with the right person ?
    Find a way to throw that it into the conversation at some point soon if not. There should be a way to do it without it sounding like you are pushing at DTR talk… more, you know, this is who I am and I’m not really into the whole “hook up” thing

    Like, you could say you have a friend who is on tinder and having a hard time meeting a guy that wants more than sex… and ask him what he thinks she should do and what he thinks about FWB situations, etc.

    What i mean is you find a way to discuss your attitudes around these things without making it specifically about you guys.. in the way that one might discuss wanting kids hypothetically one day without making it sound like they mean WITH THEIR DATE.

    #713653 Reply


    Yes, Jules, it will make it strained and awkward. He’s asking you out on actual dates, so I think it’s best if you assume the best until he shows you otherwise. If he saw you as a f*ck-buddy, I doubt he would have asked you out, he probably would have invited you to his place even later at night.

    If I were you I wouldn’t try to have a big conversation about it yet. Keep it natural and in the nice flow you’ve had so far. You can’t go back and erase what happened even though you wish you’d taken it slower, but you got in the moment and took things in a different direction. So embrace that and move on. Don’t try to “fix” things and turn them around.

    Rather than a big conversation about it, maybe address little things here and there as they come up. Be honest about who you are and what you want. Date him for a while and get to know him. At this point you can’t even know how into him you are, you have to get to know him better. So take the emotional part slowly. If things go well he’ll be trying to lock you down within a couple months.

    #713666 Reply


    Hi-I agree with most of the advice given, except the ” Story about a friend on Tinder,hypothetical discussion etc.” That sounds contrived and unnatural. I agree with Anon’s last post.

    #713681 Reply


    Thanks everyone!

    #713703 Reply


    You don’t want to be seen as a fwb but you jump his bones the first chance you get. Let me guess. You NEVER do this on the first date, ever!

    #713704 Reply

    Anne ohio

    I think you should take control and simply tell him you need to plan an earlier date, or one that doesn’t include drinking. Then drive home. Keep some mystery in the mix, don’t let it all hang out yet by spending the night, breakfast together etc. Let him wait and build some mystery.

    #713723 Reply


    Go for it and have fun. Be yourself.
    Ask him what hes looking for asking you out again and listen. Tell him how his behaviour at the wedding just blew you away and how he is the sort of guy who is right up your street…but let him know, you’d like to get to know him better and if you’re compatible then he’d be someone you’d definitely consider seeing seriously- if the sex was good tell him that also.
    After that leave it to him – and have the mind frame, of it’s meant to be it will be – do not get attached until he plays his cards how you want them
    You have every right to have sex with whomever you want – just don’t ‘expect anything and see how it goes.
    Good Luck

    #713726 Reply


    pro tip – keep your legs closed on the first date if you want to be taken seriously. you’ll only be seen as a fun time to this guy now, but that’s your own fault. and i bet you neverrrr do this, right? i call BS — have some self control. and self respect.

    #713727 Reply


    I’m with Janet on this one. You’ve already jumped way past the “getting to know each other slowly” phase, so you might as well enjoy and have fun – AS LONG AS you’re willing to sit down and have a talk about where this is all going.

    Never expect a man to read your mind. There are plenty of fun, friendly, playful ways you can tell him you expect to be more than just a FWB without turning it into a ultimatum or a challenge.

    Sometimes when you’re both lying there basting in your own sweaty afterglow, all it takes is a big brilliant million-megawatt smile and a “So does this mean I’m your girlfriend now? I get to take you off the market?”

    #713728 Reply


    I agree with Anne Ohio, ask for an earlier date and leave the booze behind.

    If you keep up with the overnights and sex he may in fact see you as an FWB.

    I see nothing wrong with slowing it down a bit. Get to know the guy and find out what he is looking for.

    #713772 Reply

    Devil’s Advocate

    Have to agree with Joe on this one! Simple solution is to simply only have 1 or 2 drinks and stop drinking an hour or more before you drive home. Men pay attentions to actions, if you are drinking and spending the night you would probably wind up in bed with him again and we all know it!!!

    #713774 Reply


    Agree with Joe and Devil’s Advocate.

    Also don’t say, “I never do that on the first date…blah, blah.” You are an adult and that is what you did. No regrets. Nothing to apologize for or bring up.

    Also, do ask him what he is looking for when it naturally comes up. Or find a way to bring it up where it flows with the conversation. I am going to respectfully disagree with Janet on this one point. Don’t bring up the sex. You don’t want sex to be the focus. I agree with Janet in being yourself and having fun.

    Have fun, be your best self. Go on a few more dates without ending up in bed so you can judge for yourself if you want to keep seeing this guy. Have fun!!!

    #713781 Reply


    Y’all know she won’t follow the advice and will be on here after the second date saying she spent the night. Smh. May work out or not, but if you want the best chance of a boy friend don’t give it up so easily and invite pretty much a stranger to a wedding event, it’s too much too soon. He didn’t earn the privilege. He never even put out a dime to take you in a date, and now wants you to drive distance to spend the night with him. How does that sound to you? Like a prize or a desperate woman? I have done first date all night and sex but it was on the man and not on me. Makes all the difference. You basically paid for the first date and gave him sex without him doing a damn thing. Tread carefully because he might think you do this with most guys unless he views you as really special he won’t want someone like you as a girl friend.

    #713795 Reply

    T from NY

    I don’t agree with most of the thread — but that’s because I only want to date men who are ready and open and would never judge me about when we slept together. YES. It is absolutely true that some men will. I’ll leave those to the rest of the ladies. I have had multiple – years long relationships (one that was two decades) where sex happened on the first date or very closely thereafter.

    This guy is gonna choose you or he’s… not — is how I feel about it. Just be yourself. Stopping trying to shape the thing before you even know what the thing is! Besides I think your obstacle is not being seen as a fwb, as much as it is the distance! Very, very few men can handle long distance for long. Takes a special guy.

    I say go and have a great time. Of course talk about what you’re looking for when it comes up organically. But stop worrying “what this is” right now. You don’t even know him well enough to know if he’s worthy of your devotion. And i think it’s silly and somewhat manipulative to withhold sex now. It’s my opinion that if a man is open to a relationship, and he’s mature and level headed, bedding him quickly isn’t going to scare him off. If he decides not to see you as a girlfriend I don’t believe it will be because you spend the night. Besides — if you express what you’re looking for on this date and he says he’s looking to “just have fun” or anything along those lines — just keep the drinks to a minimum and drive home.

    Be confident and calm and just have fun. What’s meant to work out — will. Going forward if you really like a guy — you can make a choice to not sleep together so quickly. But it’s done. Stop having expectations and just relax and find out more about him. Good luck

    #713951 Reply


    I think you should be more concerned about the fact that he picked a place closer to him knowing that you need to drive an hour home. He can’t just assume you will or can stay over. It’s not even about you had sex with him or not, it’s the lack of consideration. In addition, even if you stay over, you don’t need to have sex with him. If you’re not comfortable then don’t, nothing is wrong with that.

    #714162 Reply

    Anne ohio

    OP, what happened on the date?

    #715201 Reply


    Honestly, it was great! And we have been in contact and having a very nice, gradual getting-to-know you process so far. Thank you for asking. Whether it works out in the long run or not, he’s a very kind and good guy, and I am enjoying getting to him. We’ll see what happens. And thank you to those of you who gave kind, responsive feedback. I was reading, and I truly appreciated them.

    To those who responded with insults and trolling remarks — You’ll have to let us know how you reached the level of life-mastery you’ve achieved, so we can all start making perfect decisions and always know exactly what to do all the time. Then you won’t have to spend so much of your precious time ridiculing the rest of us. I follow these forums from time to time and have noticed several people who consistently come on here to tear OP’s down and make fun of them. To those who said “I bet you never do this, right?” — As a matter of fact, no, I don’t. But I didn’t say that because, clearly, I did this time. C’est la vie, we’re all humans and make faulty decisions sometimes, over which we sometimes torture ourselves. The pleasure you take out of rubbing salt in the wounds is very telling of who you guys are, and your words carry very little weight. Keep living your best lives.

    #715204 Reply


    so You had a second date. Good for you. Did he f you again

    #715255 Reply


    Stupid… You act reeaaallly stupid. Please go away. You are acting like a troll, and are extremely mean…

    #715256 Reply


    you gradually get to know someone and take your time and slowly get to know someone that you had sex with in the first two dates. Yes getting nude with a man the first two times you meet him is taking things really slow. Makes sense

    #715258 Reply


    “Stupid” has already been banned once and think it won’t happen again so thinks can say whatever. Not true…. “Stupid” is the one who is stupid. Been reported to Eric.

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