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That time of year right when fall starts when it is best to get a girlfriend to settle down with for the Winter, only to dump her come spring time, hence the seasonality of the relationship.
Dude#1: I love the start of Football season !
Dude#2: Yeah now that summer is almost over and I can't chase bikini's around the beach anymore it's also girlfriend season.
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The time period roughly between November to February, where a single person feels extra pressure to bring a suitable mate to holiday parties and family gatherings. This pressure often leads to picking the first available/willing partner. The forced relationship is often dragged out until just after Valentine's Day.
Another phrase for cuffing season.
(At a family gathering)
Cousin A: Who's that skanky girl holding hands with Brian?
Cousin B: No idea, never seen her before.
Cousin A: Well, it IS girlfriend season, I guess he had to bring someone.