wedrifid comments on Scientific Self-Help: The State of Our Knowledge - Less Wrong
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Aside from the possibility that you had a bad breakup and you end up complaining for several minutes, which isn't a good sign in a date. It raises the question of "What did those people find out about this person that I don't know yet that it caused them to break up with them.".
And: "If he is bitching about his ex to me then chances are he would bitch about me to others too." Possibly applies even more for boasting.