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Originally Posted by Mantus
About flings. They can happen for many reasons. For example, sexual projection is a powerful thing.
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To give another example, loneliness is also a powerful thing. Sometimes a guy can feel lonely and unhappy, and having a companion for the night can erase these feelings. Sometimes the field in which to choose from is not dense with underwear models, so an "unfortunate looking" one is all that's available.
As a side story, when I first started getting serious with my SO, she also questioned some of my "unfortunate looking" past choices (to her, not me), and it made her wonder if there was something wrong with me. She equated my taste in these women to her somehow. On the flip side, I have also dated some long-legged blondes with big breasts. This also made her uncomfortable about me, like I was superficial. Sometimes you just can't win.