This comic strikes a chord with me, and not just because I’m often not sure I like having fun. From time to time people say things to me like “women aren’t magical creatures whose motives can’t be figured out by mortal man” and “if you think a girl is into you, you’re probably right,” and, fair enough, I’m sure those are true as generalizations. With respect to the second in particular, though, my experience has been that I’m actually a terrible judge of whether a girl likes me or not. The thing is, while it’s certainly true that a girl who likes a guy is likely to try to give signals to that effect, it’s also true that women are socialized to be nice to guys in general, and it can be really difficult (for me) to tell the difference. It’s also true that some people flirt just for fun without meaning to imply any actual attraction, so even obvious flirting isn’t a surefire sign that someone is interested.
The upshot of all this is that when a girl is friendly and flirtatious toward me I am not at all confident that she’s actually into me sexually. The only way to find out, of course, is to make an explicit move myself, but when I’ve done that in the past the result has usually been that it turns out she’s not actually interested and was just being friendly or whatever. The most depressing examples of this dynamic were in college, where I would get this sort of rejection from girls that I wasn’t actually all that into myself and was only pursuing because I was so lonely. This happened several times, and it was a major blow to my confidence and disincentive to trying to hit on girls from then on. Putting your arm around someone and having her recoil in horror is an awful experience and it makes you not want to end up in that situation ever again. In retrospect there have been several very clear opportunities since then that I’ve foolishly passed up because of that lack of confidence.
The problem really began for me in high school, but it was in college that it manifested as a clear and consistent pattern. One obvious inference from this is that I didn’t go to the right college for me in social terms, but it’s hard to imagine how I would have been able to figure what would have been the right one given the information I had available when I was making the choice.
Ultimately I think this can all be classified under “patriarchy hurts men too.” The expectation that the man will make the first move means that the only thing a woman can do if she likes a guy is send whatever subtle signals she can, but to a lot of socially awkward guys those signals are indistinguishable from the routine signals women send to ingratiate men in general. If women weren’t required to send those ingratiating signals, and if they were able to make the first move themselves if they were inclined to, this would be much less of a problem. (Online dating does remove a lot of these problems, but it adds some additional difficulties and frustrations of its own, so while it’s better on net, it’s still kind of a pain.)