Top Definition
The optimum time of year to date (in the U.S.) begins Feb 15 (after Valentine's Day) and ends shortly before Thanksgiving. Starting a relationship close to February 14th can be awkward on Valentine's Day if you're not REALLY into that person (yet). Also, meeting family around Thanksgiving can prove to be more than a relationship can handle. Lastly, if you're playing the field around the holidays, buying multiple gifts for multiple partners can get very expensive. Plus, being multiple places at once is impossible.
Dude, don't get serious with that chick until Dating Season begins. It's too close to Valentine's Day for you to NOT make a big deal of it.

Dating Season is almost over! You better decide now if you're serious about seeing him because you know he's having his family in town over the holidays.

Come on man, Dating Season is almost over. Be with ONE girl or let 'em both go. You can't keep both of them happy if you're going to continue to be "too busy" during the holidays.

I gotta dump him. Dating Season is almost over and there's no way I can afford the girl's weekend in Vegas AND buy him a Christmas present.
by wordsmithologist January 28, 2011
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