Is the prize that you are going to move to California?! Because I win! I can surely answer your first question.
How come she just can't realize she's great, and that the bad decision of some jerk-off doesn't mean she's unloveable?
The reason you start to believe you are unloveable is because of the evidence. There's, like, so much evidence. There's the part about how you're single. It is hard to deny that part, on account of how there is no one else in bed with you at night. There's the part about how you really liked that guy, and you also liked that other guy, and both times things were promising, but then they didn't choose you. And your longterm boyfriends didn't choose you either, or else you'd be married now, wouldn't you? Those parts set the stage, but the real soul-destroying part comes when you make comparisons.
That's when you look at the couples you meet, and you discretely check out the woman and you wonder, why her? What is it about her? How come she is a person that a man will propose to and I am not? Sometimes it is easy to understand. Because she is freaking kick-ass, and I would totally propose to her too. Because they are absolutely perfect together and look at each other with lovey-eyes and of course they should be together. Those cases are easy and cause no grief.
The hard case is when you meet a totally charming guy, someone you would would date were he single and his unimpressive wife. Then it is all I can do not to stare. Why? She is not so special. Flowers don't spring up from her footprints. Rubies don't drip from her lips. She seems perfectly nice, but she isn't all that witty and if you must know, I think the bangs are kindof a mistake. Not that she doesn't have nice skin, but how did she land him? What is she that you are not?
The first answer that you have to fight off is that she is thinner or prettier. That's what she is and you are not. This is a tempting answer, except that it doesn't fit the evidence either. That woman who is married to a man I would very much like is not thinner than I am. Actually, she looks a little soft and roundy, and his hand still slips down to her ass when they stand together. Besides, I have been different amounts of thin and pretty in my adult life, and while I get more attention at thin, I don't get more devotion at thin. This is the explanation our mainstream consumer culture tries to tell us, but when I watch in real life, the correlation just isn't there.
So you watch, and you see that other women are clearly loveable, and after a while, you rule out all the qualities that make them different. They aren't all more physically attractive; not all of them are wittier or prettier; some are sweeter, but some surely aren't. Finally, all the potential explanations are gone and you are left groping in the dark and you settle on what may be the worst explanation of all. There is something ineffable but noticeable to men, a mysterious invisible broken something inside you. Your girlfriends can't see it, and your married male friends tell you you are being ridiculous, but it has to be there. Else why are you single, and for so painfully long?
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The funny thing is that even though I can still write about that feeling (and I could add another three or four people to your collection of people who think they are the only secretly unloveable ones), I've moved really far away from it this last year. I've got new ways to think about this stuff, and I've been working with some new theories, ones that feel a million times better. In fact, I have discovered a truly marvelous proof of these, which this margin is too narrow to contain.
UPDATE: I very much liked this from AWB's response.
Megan goes on to talk about how watching all the men you like fall in love with women who aren’t you leads to an ugly sort of comparison-making about looks. I don’t find myself doing that, in part because I think attractiveness is way too weird to be understood. But I do watch the straight men in my life get totally swept off their feet by women who don’t seem very interesting to me. And I hate seeing myself do that, because even temperament isn’t any more understandable than physical attractiveness.
Yes! All of it is too weird to sort, and neither looks nor temperament win love. I'm increasingly convinced that they're on a non-intersecting plane entirely.