Mmm, romance(?)

I just submitted the thing below to Washington Post advice columnist Carolyn Hax, who will probably never answer it. And so I toss it to you, my friends and acquaintances and trolls, because you always have useful things to say.

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Carolyn,

How do I know whether I like someone or just like to be liked? I need a good rule of thumb, or something.

Oh, and I have a weirdly related question: How do I know whether a woman is too good for me? I need a good rule of thumb for that, too.

For context, for the past few weeks I have been going on dates with three women I met online. They are super impressive people with so much intelligence and wit that it seems unreasonable for a guy like me to be associating with them. And they’re attractive to boot.

Of the three, I have an early favorite, but I am worried about having her as a favorite because she seems better than me in every way. Most disturbing is that she beats me in all the things I thought I was not bad at: She can own me in any intellectual debate, including ones in my own field; she can out-write me; I’m pretty sure any objective critic would say that she would win the taste-in-the-arts battle; and I used to think I was wise for a 20-something, until I met her. Despite all that, for some mysterious reason, she continues to agree to go on dates with me, which probably means she’s also way kinder than me.

Although I have a favorite, right now I don’t want to stop dating any of the women. Partially that’s because I don’t know them well enough / they don’t know me well enough to make any final decisions, but I also have this lingering suspicion that my motivation is more to find someone who likes me than to find someone I like. I’m wondering whether I might be keeping my “options” open just to hedge against rejection and bask in the feeling of possibly-being-liked. And the thought makes me feel kind of grimy.

But motivations are enigmatic creatures, and I’m wondering what advice you can offer about revealing my motivations to me. Then again, maybe I’m thinking about this in a completely wrong way, and in that case I’ve set you up perfectly to work your magic.

-- A guy who wishes he could come up with a clever pseudonym.