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Pretty clearly it's less painful if she moves on to Brad Pitt. In that scenario, the assumption is that she moved onto someone for his looks and that you can't really change what you look like.
If she moves onto a guy who is a loser, she's saying that she would rather be with a guy with no future than you. Ouch.
Of course, since we're talking high school here, there's also a third option that is "She's batshit crazy and doesn't know WTF she wants."
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