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It seems like that's the cycle that I'm stuck in. I take a lot of time and care with my appearance. I have a good makeup routine, and I dress nicely everyday, trying to stick with the trends. I would consider myself pretty attractive.
The guys that go for me are never that. It probably has to do with my personality. Although I dress like them, I don't act like 'plastic' girls, the ones that are popular and usually quite dumb. I'm very loud and proud about being myself, which means I am unapologetically and passionately a nerd and quirky. That attracts guys that would otherwise find girls intimidating, in my opinion, because I am open and welcoming to everyone.
I've gotten some pretty unnatractive guys. I actually dated one with a pedo mustache. That was a bad relationship. I gag every time I think about it. Of course, that was an extreme, and the gagging isn't from the way he looked but from the emotional suffering I endured during that relationship.
Now, I'm dating a guy who is a large step up, in my opinion, from the last one, but I don't think he is extremely attractive. It just tends to happen that the guys I date are the nerdier type and therefore don't have the looks that I am usually interested in. Still, I care about them nonetheless, and this guy is truly a godsend.
In short, I definitely would date a guy that is less attractive than me as long as I am not disgusted by the way he looks. This is what tends to happen anyway. I stopped trying to get guys that I was attracted to a long time ago and realized I should just settle for these absolutely amazing guys that are just a bit less handsome.
I think it would be weird to compare my looks to a guy's. I'll date a guy only if I personally find him attractive. So it doesn't matter if someone else doesn't find him attractive or think I'm more attractive than him thus I should date someone with the same physical appeal as me.