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.
It doesn’t matter if you’re single, taken, or somewhere in between—you probably have a ton of questions. How much should you spend on a present for your three-month friends-with-benefits? Whose family do you visit, hers, yours, or do you go your separate ways? Is it a total faux-pas to break up with her on New Year’s Eve?
Chill out! We have all the answers in this guide to dating over the holidays.
Being single during the holidays can be difficult, especially if all your friends are paired off (and spending time with their significant other). 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. “People are in ‘relationship mode’—they want to meet people and make connections.”
The key to meeting your future girlfriend—or holiday fling—is to put yourself out there by hitting up as many holiday parties and singles events as you can. It’s not a great idea to try to hook up with someone at your own corporate holiday party, because tsitoften lead to regret (especially when spiked eggnog is involved), but your friends’ corporate holiday parties are fair game. Just remember to keep it classy: Don’t get drunk or inappropriately hit on your buddy’s boss. “It’s never a bad idea to ask the host or the person who invited you about someone you’re thinking of pursuing,” Sullivan says, of both corporate and regular holiday parties. “It’s respectful—you don’t want to step on any toes—and it will give you a chance to find out more about that person.”
Because the holiday season is full of potential, Sullivan suggests keeping your options open when you’re out and about. Coffee shops, where people gather to socialize and escape the cold, are a great place to meet women, as are malls and shopping centers during the shopping season. Local events in your city or neighborhood, such as tree lightings, pop-up ice skating rinks, and holiday festivals will all be teeming with single ladies who are open to meeting someone new.
The two big things to think about if you’re already partnered up for the holiday season are finding the perfect gift for her and social obligations (including family time).
If you’ve just started dating, or you’re still in the beginnings of the relationship—let’s say you’ve been together less than six months—any gifts should be cheaper but still personal. “Keep it simple,” Sullivan says. “Too much too soon, and you’ll scare her off.” Jewelry, for example, is tricky and very personal—and can come across as ultra-serious—so Sullivan suggests staying away from it for the first year or so, at least. For a casual or new relationship, your best bet is to give her something low-key with personal meaning, such as a book from an author she loves or a box of chocolates from a country she wants to visit. If you’re past the casual dating stage but you’re not engaged or married, Sullivan suggests splurging on something the two of you can do together, such as a concert, a fun day trip, or a couple’s cooking class.
When it comes to serious long-term relationships—living together, engaged, or married—romance is key. “The holidays can be stressful, so it might be nice to plan a vacation or a trip so the two of you can get away and rebuild your bond after you spend time with family,” Sullivan says.
As for social obligations, such as visiting family and taking her as your plus one to holiday gigs, the question is mostly about how serious you are. “You really need to have a clear conversation about what the relationship is and where it is—or isn’t—going,” Sullivan says. You might think that it’s easy enough to tag along with her family over the holidays, but many women will read into any “meet-the-family” scenario (whether it’s you meeting her family or vice-versa) as the relationship being serious.
It’s always a tricky question: Do you break up with her before the holidays, and risk ruining her entire season? Or do you break with her after the holidays, and risk being the asshole who dumped her two weeks before Valentine’s Day?
The answer is easier than you think, according to Sullivan: Before. Definitely before.
“There’s no good time to break up with someone,” Sullivan says. “It’s always better to do it sooner rather than later. Plus, during the holidays you know she’ll be around her family and friends, so she’ll at least have a good support system.” Earlier is better, but if you absolutely can’t bring yourself to cut ties with her before the holidays, Sullivan suggests that you distance yourself from her throughout the season. For example, instead of heading to her family’s cabin for Christmas, tell her you’d rather spend time with your respective families over the holidays—it will make the breakup less painful. “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.
“Think of how you would feel if she dragged it out for purely selfish reasons,” Sullivan says. “Break up with her and go to the party alone if you have to.” Read how to break up with her (the classy way) if you’re struggling with approaching the uncomfortable situation.
Dating
