Between Thanksgiving Day and New Year’s Eve, your calendar is booked with house parties, office shindigs, trips, and fundraisers. ‘Tis the season to bring a date! We’ll help you make a good impression in these common holiday social situations.
1) Ice Skating—Don’t Freeze Her Out In the girl world, ice skating is the winter version of a romantic walk on the beach. I remember going skating once with a guy I was massively crushing on and he totally blew it. When he tore into the rink, started cutting up the ice, and skated circles around me (crouched in the rough approximation of a speed skater), I knew that he wasn’t worth my time. What a douche!
Unless your date is an Olympic hopeful, she’s not going to consider an invitation to the rink an opportunity to get a work-out in. Every woman I know—from the college cheerleader to the Big Law partner—wants her hand held when ice skating. And if she falls (perhaps intentionally—yes we can be that devious), you’ve got the perfect excuse to brush off her wet booty and cheer her up with a cup of hot cocoa.
2) Get Multicultural Before you start going on about The Baby Jesus and singing your favorite carols at the top of your lungs, stop, drop, and ask yourself, “Is she Jewish?” I’ve known “non-practicing” Jews who go feral on people who aren’t sensitive about this issue.
With so many shopping mall Santa’s and Christmas trees in your face, it can be easy to forget that some people don’t celebrate Christmas. Don’t make this mistake. Likewise, is she a Jehovah’s Witness? Muslim? Does she celebrate Kwanzaa in addition to Christmas?
3) Rocking the Holiday Sweater A holiday sweater is a great way to sport your spirit and get laughs out of her, but there’s a fine line between cute ugly and just plain fugly. Be cautious when breaking out the outlandish, and disgustingly joyful sweater your grandmother knitted for you.
If it’s got blinking lights, bells attached, or makes any noises whatsoever, you’re really screaming, “Hey, look at me! Hey! Pay attention to me!” Not cool. Unless you’re sure she’s got a high tolerance for wackiness, leave holiday sweaters that require batteries at home and let her be the center of attention.
4) The Weekend Ski Trip Is the point here to score with her, or score a group discount? The main thing is to be clear about your intentions. Even if she’s stoked about hitting the slopes, I promise you she’s also got romantic evenings snuggling in front of the fire in mind.
If you’re thinking more along the lines of evenings over a game of cards with a six-pack with five of your best buddies and your girl, make sure you make it clear that it won’t just be the two of you. She may love hanging out with your friends for the weekend, but she may not want to pack the lingerie.
5) Choosing Holiday Drinks When mixing holiday-themed drinks for your date, skip the eggnog. No one is going to want to smooch after downing a few glasses (think milk breath). Plus, eggnog is so rich that it’s likely to make your date pass out (i.e. not horny). It gets worse.
Getting drunk on this sweet stuff—if you recall from your college days—may also encourage vomiting. Unless you want to be the guy holding her hair back, skip it! Horror of horrors, if she’s lactose intolerant, eggnog could further induce some “unladylike” reactions.
Believe me, tooting does not make a woman feel sexy (yes, we fart!). As a safe alternative, try holiday-themed cocktails liked spiked apple cider or a hot toddy.
6) A Night at the Theater “Family friendly” performances are showing during the holidays at venues normally reserved for a more sophisticated set. How confusing! Don’t fall into the trap of getting tickets for performances of The Nutcracker, The Radio City Christmas Spectacular, or Christmas at the Pops.
Avoid the baby herds and sticky fingers. You’ll have plenty of time to catch those shows once you’re tied down with 2.3 kids and a pair of cranky in-laws. Might I suggest a few adult alternatives: Handel’s Messiah, holiday jazz venues, or a chamber music concert.
7) Wha’ Elephant? She’s invited you to a party with a White Elephant gift exchange. If you don’t know what that is, in a nutshell it’s a sort of Secret Santa where participants are able to exchange their gifts for better ones, without the permission of other participants. Now, you’re not sure what to bring, but not participating is lame!
You don’t have to hit up Spencer’s or pack the fine china. How do you pick a great White Elephant gift without breaking the bank? You know, one that everyone fights over or makes people pee their pants laughing? Think re-gifting.
Choose something you don’t need but isn’t obviously used. Sometimes, practical items end up getting fought over, like that iron your roommate left behind. If you’re going for a laugh, that’s cool too, but make sure the gift is audience appropriate. Save the roadrunner-shaped bong for another day (I speak from experience here).
8) Always Bring a Scarf or Hat Even if you’re a macho, tough guy, the point is to have something you can easily part with if your date gets cold. Contrary to popular belief, we’d rather borrow your hat, scarf, gloves, or ear warmers than your coat.
It makes us feel really, really guilty if you lend us your coat and start noticeably freezing your balls off or, even worse, insist that you aren’t cold even as frostbite sets in. Also, a small item like a hat or scarf is an easy thing for us to “forget” to return at the end of the night. What a great reason to see you again!
9) Volunteering Dates The holidays offer ample opportunities to give back to the community. You can’t go wrong with a date centered around volunteering. Or can you? Don’t let your over-zealous desire to spread the holiday cheer get in the way of the date. Make sure you choose an activity that allows you to work together and actually talk.
For example, wrapping gifts for a shelter is a fun way to give back to your community and get to know each other better. On the other hand, serving food to the needy is not a particularly great date activity. When you’re running around taking care of food service, clean-up, and cooking, you aren’t going to have a second to chat with her. Besides, everyone looks unflattering in a hair net.
10) Her Office Party Okay, so she’s asked you to be her date to her office party, and it’s the first time you’ve met her co-workers. First, even if you’re absolutely positive that your holiday sweater is cute ugly and not fugly (see above), don’t do it. Second, watch the booze.
It’s tempting, yes, because the booze is (usually) free, but if you drink too much and do something stupid like, say, let slip to her boss what she really thinks of him or pass out in the corner, then the booze could cost you your chances with this girl.
Do dance with the older women but not with the young temps. Charming the socks off Barbara in senior management could give your date a huge leg-up, and she will appreciate it immensely. Making nice with a fresh-out-of-college temp, on the other hand, is going to make you look like a whore and, even worse, make your date feel pathetic in front of her co-workers.
