To second-date or not to second-date, that is the question.

TLDR: Do you think it’s worth going on a second or third date with a well-matched, decent-looking woman who’s not so attractive you’d check her out on the street?

This is about dating but not rebooting per se. I’m almost a year into online dating and I thought I’d bounce some thoughts off this forum. Basically the women I’ve met have fallen into three categories. First, there have been a handful of one-offs, dates that were pleasant enough but either she or I made it clear pretty soon that we weren’t interested enough to pursue it further. These were relatively painless.

Then there was one girl who I totally fell for. Gorgeous, good personality, smart, interesting, fun. Before long we were texting every day (a lot for me) and casually talking about doing things together in the future. She broke it off after six weeks because her ex-boyfriend re-entered the picture. Basically they had had a good, long relationship, and then broken up because she wanted kids and he didn’t. Eventually he changed his mind and convinced her to get back together. Obviously this was a tough blow for me (and for the record, she handled it well, taking a good long time to think it over).

Finally there have been four girls in between those extremes. In each case, we went on three or four dates before I broke it off, usually before we had so much as kissed. The girls were above-average-looking, good people with good personalities, whose interests and values overlapped with mine (I have a lot of interests). We’d have good, long conversations, but I didn’t feel particularly moved to escalate things physically, nor did they seem to expect it yet. After a few dates I just figured, if I don’t feel it now, I’m probably not going to feel it ever. In retrospect it seems to always go back to a judgment I made on the first date, that whatever their appealing qualities might be, this is not someone I’d notice on the street and want to have sex with.

Breaking it off with these ones has never felt good. In fact, I just did it today, and this one was particularly hard. To be honest, I’m not sure I made the right decision. After three or four decent dates, we have already bonded quite a bit, and I always feel crappy for letting them down. There’s always a voice in my head saying to just give it time. On the other hand, I’m not thinking about them when they’re not there. I’m not nervous around them. So I figure it’s not love, and it’s not going to become love, so what’s the point?

So my current thinking is that I really need to be more judgmental on the first date. If I don’t find myself desiring them physically, then there shouldn’t be a second date. But of course there is still a nagging voice that my physical standards are too high or impossible. And I suppose this is where the years of porn may play a part. For me porn has largely meant seeking out my physical feminine ideal, and I guess when you can find it so easily, and so many variations on it, you get accustomed to it. Ideally I’d get that out of my system for a couple of years before judging these women. I’d buy that argument except for the fact that I did find someone I really liked and found super attractive, and we had a good (if short) time together. Will I get that lucky again or should I lower my standards, at least physically? And should I actively strive to be a less superficial person?

Thoughts?

 

Interesting range of responses, thanks. There is definitely part of me that wants to keep dating each of these girls, just for the experience. I mean, they’re all interesting and good people in their ways, they're not unattractive, it’s better than being alone, and who knows, we could turn out to have good physical chemistry down the line. But I guess I’m at an age where most people are looking for something serious, and if that’s the expectation, I want it to be someone I really feel myself falling for. Until I meet that person, part of me wants to date around, but I feel like it’s a little deceptive if I can tell that it’s not going to last. I might have been more OK with just going for it ten years ago, but not so much now.

 

I think attraction is the main issue. I don't think I'm going to fall for someone who I haven't felt a strong physical attraction to after a few dates, someone who I don't find myself daydreaming about, looking forward to the next time I see her. I might enjoy their company a lot, we might have interesting conversations, I might enjoy the attention, but none of that is a basis for love. And as far as marriage, I'm not necessarily looking for it, but I'm also pretty sure these women are not just looking for someone to have fun with for a couple of months. I mean, if I get a feeling that they're OK with that, maybe I'm OK with it too, but I'm not going to encourage her feelings to develop if mine aren't developing along the same lines.

 

Mind not totally made up, but certainly leaning in one direction. I appreciate the feedback.

Good point about married couples. But I think it's also fair to ask is whether they started off being attracted to each other, and ask the men in particular. And ask how good their sex life is--pretty sure that's correlated with marital satisfaction. I know that's not the same thing as attraction but I do tend to think the sex will be better for me if the attraction is strong.

 

I hear you. And maybe I’ve misspoken—it’s definitely not all about looks for me. A lot of it is about fun, playfulness, flirtation. As a somewhat nerdy guy, I match well intellectually with nerdy girls, and I tend to respect them a lot as people. With some of these girls, we have interesting conversations, but without much of a sexual undertone—little in the way of touching, laughing, flirting. In my mind, those things seem absolutely essential to what I think of as romance, but maybe in theirs it’s not going to be like that until we’ve invested so much that we are basically headed towards long-term relationship territory. I guess for me, the bottom line is that respecting someone and sharing their values is not the same as being attracted to them.