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From the movie Chasing Amy, it means when you dump someone who was perfect for you for a reason that you eventually realize was not worth ending the relationship for. However, by this time it's already too late. The other person no longer feels the same way about you, but you will spend the rest of your right regretting this decision that you can never change.
G1 - I'm falling hard for this guy, but I don't think I can stay with him.
G2 - Why not?
G1 - He tries to act like he isn't, but he's definitely still in love with one of his ex-girlfriends. I'm pretty sure he's Chasing Amy.
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Excerpts from "Chasing Amy" Scene, where Silent BOB explains to Holden & Jay, why he's still chasing Amy.
BOB
You're chasing Amy.
...
BOB
(to Holden)
So there's me an Amy, and we're all inseparable, right? Just big time in love. And then about four months in, I ask about the ex-boyfriend. Dumb move, I know, but you know how it is - you don't really want to know, but you just have to... stupid guy bullshit. Anyway she starts telling me all about him - how they dated for years, lived together, her mother likes me better, blah, blah, blah - and I'm okay. But then she tells me that a couple times, he brought other people to bed with them - menage a tois, I believe it's called. Now this just blows my mind. I mean, I'm not used to that sort of
thing, right? I was raised Catholic.
JAY
Saint Shithead.
*Silent Bob backhands him. Jay raises his fist as if to
strike.*
BOB
Do something.
(to Holden)
So I get weirded out, and just start blasting her, right? This is the only way I can deal with it - by calling her a slut, and telling her that she was used - I mean, I'm out for blood I want to hurt her - because I don't know how to deal with what I'm feeling. And I'm like "What the fuck is wrong with you?" and she's telling me that it was that time, in that place, and she didn't do anything wrong, so she's not gonna apologize. So I tell her it's over, and I walk.
JAY
Fucking a.
BOB
No, idiot. It was a mistake. I wasn't disgusted with her, I was afraid. At that moment, I felt small - like I'd lacked experience, like I'd never be on her level or never be enough for her or something. And what I didn't get was that she didn't care. She wasn't looking for that guy anymore. She was looking for me. But by the time I realized this, it was too late, you know. She'd moved on, and all I had to show for it was some foolish pride, which then gave way to regret. She was the girl, I know that now. But I pushed her away...
*Everyone's silent Silent Bob lights a cigarette.*
BOB
So I've spent every day since then chasing Amy...
(takes a drag from his smoke)
So to speak.
When a guy meets a great girl, and loses her. Pride, fear & self doubt get in the way of him appreciating who he is with.
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trying to get back the girl that got away...
"you dumped her, you want her back, you're spending your life Chasing Amy"
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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!
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Trying to find Happiness/Love/Perfect Situations, usually a practice in futility. Derived from the figurative way Silent Bob uses the phrase to assist Holen McNiel in the movie Chasing Amy
Man 1: i dont know about this girl, she just doesnt seem like the one
Man 2: thats the millionth time you've said that, stop Chasing Amy and settle down with her
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When you try to have sex with a hot lesbian but she bends you over and cums deep in your rectum.
Stop trying to get with that lesbian before you end up chasing amy