Stereotypical Friends to Dating to ???

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  • Mischa
    Post count: 0
    #5108 |

    Hello! Much like the subject header suggests, I\'m stuck on a situation that deals with the icky space between friends and significant others.

    A bit of a backstory on the situation: we've known each other for 4 1/2 years, but have only been friends with little desire to do anything else on my end, and ambiguous feelings at the beginning for him which somehow ended up with me being his relationship therapist (he rants to me about how women don't like him/want to date him all. the. time.). We meet up a few times a year, chat at coffeehouses and such, and ….. that's it. However, a mutual friend expressed interest in him, and asked me to see if he would be amenable to dating her, which I quickly found out was not likely at all, due to his views on marriage, religion, and even living in this country. Totally incompatible. Even so, it sort of flicked a switch in my brain, and I started wondering if asking him on a date would be a worthwhile thing to do- after all, what is a relationship aside from a friendship with added intimacy? After asking my friend about it, she pretty much admitted that she had hoped I'd come to this conclusion, as it had been way too long since I've been on a date and he seemed like a good person to give it a go with (manipulation at its finest, I suppose). So, I asked him out and he said yes immediately. As I left that night we pecked on the lips. I was kind of giddy about it, actually, since it's been awhile since I've had the prospect of a date to look forward to, and this seemed like it might go well.

    But the date itself was terrible on my end. Planning for it was like pulling teeth- I felt like I had to push him into decisions, although I later found out he was flipping out about this to our friend since this was, shockingly, his first date ever. During the date, I had to make most of the moves, which was limited to hand-holding (though once I initiated the hand-holding, he didn't let go), a single instance where he put his arm around my shoulder, and two pecks on the lips. So, yeah, he initiated the arm-shoulder thing (which lasted for two seconds) and the goodbye peck on the lips.

    I felt like I was filling all of the awkward silences and entertaining him, instead of keeping each other interested in things… hell, he didn't even comment on how much effort I\'d put into looking good that day, when I know I looked great (especially since he's known me since the days I only wore hoodies and pajama pants to college classes). I'd made a particular effort to wear a fitted top that showed some cleavage, and, while I'm glad that he was a gentleman, I never caught him checking me out! At all! Let alone give me some sort of compliment on how nice I looked….

    In short, his lack of initiative and passiveness annoyed me. And he was kind of boring.

    Now, I have been going back and forth on whether or not to go on a second date with him. My cousin (male) said that he was just insanely nervous and that I should give him another shot. My friend who set me up with him says I should tell him that it was a mistake upfront and not string him along. My female friend actually knows him, but my cousin has the guy perspective on things, even though he doesn't actually know the guy. There's also the fact that the guy has apparently never dated anyone, which, considering the fact that he's turning 23 soon (I'm a year and some change older) is terribly odd.

    Personally, I was really disappointed in the date, and I know my friend well enough to know that he will definitely be passive in a relationship instead of initiating things. While we were on the date, he asked me why I asked him out and I told him upfront that our mutual friend had led me to see that he was dateable, and I was curious about it, which he said was more or less the reason he said yes. So, I guess it's a case of \”why not?\”

    I think I may have made a mistake in asking him out, but I don't want to ruin the friendship. Or hurt his feelings. Or am I writing things off too quickly?

    So, yeah, any advice you could throw my way would be appreciated.

  • Martin
    Keymaster
    Post count: 250

    Hey there Mischa,

    No idea why it's his first date at that age but the point is, it was. He would have been extremely unprepared as well as highly nervous, amongst other emotions.

    The questions you might want to ask yourself are:

    [1] Am I impatient or dissatisfied with this person's qualities at this time?
    [2] Does this guy have the foundational qualities that I'm looking for because, if he does, I'm prepared to get to know him better as well as show som patience so he can come out of his shell for me.

    From what you've already indicated, you're already annoyed and bored with him so that speaks volumes.

    A second date will show further interest in him. If that turns to crap, it will likely impact on him poorly. The signs are already there that this guy is not the one you seek.

    Forget the second date, avoid any sort of teasing language, reaffirm with him that that first ‘date' was just plain weird for you and you prefer him as a great friend and buddy. Leave it at that.

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