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After a couple strong drinks and a rousing conversation about the merits of mid-century abstract expressionist painting (we’re art nerds), I asked Heather on a second date. Heather is a painter, entrepreneur and self-made super-woman.

I’m a musician, designer, and occasional tech-meddler.

But the holiday season—from the beginning of November through New Year’s—is actually a great time to be single, according dating expert Sameera Sullivan, founder of matchmaking service Lasting Connections.

“The holidays are a very busy season for the matchmaking business,” Sullivan explains.

Is it a total faux-pas to break up with her on New Year’s Eve? Being single during the holidays can be difficult, especially if all your friends are paired off (and spending time with their significant other).

“Whatever you do, don’t make more memories with her before you break up,” Sullivan advises.

Oh, and if you’re thinking of keeping her around just so you don’t have to rustle up a last-minute date to your office party…don’t be that guy.

Dating—whether you’re swiping right on Tinder or getting ready to propose to your (hopefully) future fiancée—is tricky enough most of the year.

But during the holiday season it gets especially tough, thanks to all the memories, oxytocin, and emotional gift-giving that takes place.

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