Top Definition
Gateway Douchebag
-noun phrase

1. a vaguely distasteful man who pursues young women, and persuades the women that this behavior is not only acceptable, but desirable in choice of mates.

2. a man whose behavior with woman colors their early perception about dating, usually in the negative.

3. a "Jason Levy"
Jeff: She Annie is 18. Her taste in men hasn’t been established. Creepier and creepier dudes will start thinking of her as an option, and it all starts with Vaughn. He’s a gateway douchebag.

-from (NBC Comedy Show) "Community"
by greggieG February 07, 2010

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