To be so freaked out by a girls sexual past because it makes you insecure, inferior and/or scared that you take the foolish step of dumping her, even though you still love her. Later on you realise of course that you f#cked up big time and try to get her back and look like a f#cking idiot.
Bitch, I don't like what you did with those and your ex! Fark you, i'm leaving......oh fark, what have I done! Bitch, come back, I need you!
by Clarry November 12, 2004
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Named after the same story that Silent Bob tells in the movie gets it's title from, Chasing Amy Syndrome typically happens when a girl is far more sexualy experienced than the guy in a relationship because of sexual stereotypes and cultural expectations. Gender reversal can also happen, but is not as common.

Symptoms are:
-Irrational jealousy of past lovers and/or people the girl hangs out with.

- Inexplicable "need" to push their own sexual boundaries to feel "on par" with their partner, in spite of not being interested in that prior.

- Fixation on partner's sexual past.

- Feelings of inadequacie due to partner's experience.

Typically the symptoms start after partners have traded their sexual numbers or when a story about a past tryst that is out of the other partner's league comes up.
The only known cure is for the sufferer to get the fuck over themselves and realize that their partner wants to be with them for a reason. To help this process along it is recommended to have a painfully open and honest dialog between the partners, both being open to the other's opinions and feelings.
Jill: "After Max heard I had 15 past partners and had tried an orgy he started getting weird and angry at me for stupid stuff!"
Sue: "Max only has had 3 partners, it's classic Chasing Amy Syndrome."
by Loki's SongBird November 21, 2014
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When a guys falls for a woman he can't have that's usually not interested and/or lesbian. The guy is a beta orbiter but wants the woman he can't have.
DEAN: What's wrong with Cyrus?
BILLY: He has the Chasing Amy Complex. This is never gonna work for him!
by Kenny Rice May 20, 2016
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