Hi Doc,

Despite all my efforts, my dating life has been awfully devoid of romantic connections, and I have an inkling that I might be creating that problem for myself. Maybe you can help clarify things.

Some background: I’m male and 27. I used to be a shy kid in school, had few (but mostly close) friends. The very idea of opening up to someone romantically was scary and embarrassing. Having blossomed at university, I found what I’d like to think of as my true self. I’m a lot more outgoing and charismatic than back then. Finding friends has become easy and I have a bunch of interesting and social hobbies. And about five years ago, I started dipping my toes in the dating pool and conquering my fear of vulnerability. Huzzah!

Fast forward to now: I’ve gone on first dates with almost 60 women, most of whom I got to know through Tinder and OKCupid. Rarely was there a second date, which I understand is somewhat par for the course online. And exactly twice has there been a connection that was more than “kind of a nice person, but nah”. In both cases, things fizzled out around date three. That, frankly, is frustrating.

One of the conclusions I’ve drawn is that while I think I can play the online dating game fairly well (i.e. find people to go on first dates with), it doesn’t feel fulfilling. The whole experience is just more interesting and intense IRL. That I can work with. But conclusion #2 stumps me: I think have a hard time flirting.

On the one hand, I find it hard to show romantic interest in someone, in particular in groups. “What if everyone sees I might be into her?!” On the other hand, I tend to question my interest. I often wonder how much interest I should have in someone in order to ask her out. What do I need to feel or think about her in order to get physically close? Sure, she’s interesting and I like looking at her – but is that enough to warrant the occasional light touch here and there? I have a hunch that since I don’t overtly/physically flirt in these situations, the women I’m on dates with never get a chance to actually feel if they are, in turn, attracted to me. So it looks like we’re not attracted to each other (or we’re both unsure) but we might hit it off if I just took that leap.

Does that make sense? If so, what can I do apart from making the steadfast resolution to flirt physically (and then chicken out)?

Organic Chemistry

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