rastilin 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.".
Yes. Complaining about your breakup allows the other person to locate and privilege various unsavory hypotheses about you which may or may not be fair. Don't let people do this. You aren't being more "honest" by giving people true information that will bias 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.