8 Survival Tips for Winter Dating

It's hard to be optimistic for a date when you have to schlep through the snow to get to it. But keep your chin up ... and your boots buckled.

winter couple
(Image credit: Noel Hendrickson/Digital Vision)

As I was saying yesterday, the winter months can be an especially rough time for dating, because it's just so damn cold that no one wants to go out and socialize. (Especially not in cities, like New York and Chicago, where so many of us depend on public transportation to get around — which often means lots of schlepping through the snow to get to the subway.) And even in parts of the world where people spend more time driving, everyone wants to be outside as little as possible. And no matter where you are, it's hard to feel sexy while wearing wool stockings under your jeans.

So, how do you keep your chin up during the season? A few ideas ...

1. Accept that you'll have to sacrifice a little style for comfort. And keep in mind that nothing is more attractive than being comfortable with yourself, and feeling at ease with what you're wearing.

2. Remember that winter clothing flatters everyone. It's hard to look bad in a good black sweater — whereas it's quite easy to look bad in a good white tank top, or a good flowery sundress, or a good mini-skirt. So get out your favorite tight turtleneck or loose cardigan, and feel free to wear the hell out of it for the next few months.

3. Invest in a pair of comfortable, stylish boots. The winter used to depress me so much more before I got a proper pair of attractive, comfortable, orthopedically-correct, waterproof boots, similar to this pair. I can walk for miles with these things — in the snow, even — and I never feel miserable, not even after a date gone awry. And I know they will last forever.

4. Spring for a good down jacket. Another thing that vastly improved my wintry mood a few years ago was getting a good down-filled jacket that goes down to mid-calf. My friend Daisy Milliner realized that my number was so much warmer than her wool overcoat that she got herself a very attractive belted down jacket at Uniqlo for under $200 — and they've got a number of down-filled options for less than $100 on their site. This is another item that, like a good pair of black boots, will never go out of style. (If you can't afford anything right now, I understand! But perhaps you can ask your parents or siblings to get you one for the holidays?)

5. Keep in mind that a bundled-up person brings out a human's tender instincts. When I see my petite friend Daisy tucked into her enormous jacket — or my boyfriend Sweet Pants with six layers under his hoodie (and a pair of DeWalt de-fogger goggles to prevent his eyes from tearing when he rides his bike in sub-freezing temperatures) — I just want to hug everyone in the whole world. Which is a long way of saying you might not look terribly sexy in your winter gear — but I bet you look pretty darn cute.

6. Try wintery activities on a second date. Play a first date safe — because you don't want to set out on a back-country snow-shoe expedition with someone who might be a sociopath. But if you find yourself planning a second date in the near future, consider doing something wintery and replete with romantic connotations, like ice-skating, or sipping spiced cider at a bar with a fireplace (like Tabard Inn in D.C. or the Union Square Lounge and Ballroom in New York). Or simply take a winter walk around a local park or pond, or over a favorite bridge — and then get some hot chocolate. Research shows that physical activities make people feel more bonded ... and getting out there into the cold weather will help you to feel exhilarated by, rather than overwhelmed by, the temperatures.

7. Have a pot-luck singles stew party. The great thing about stew is that you never have to worry about getting the timing right, or having all your guests show up on time. Once the stew is made, it just sits on the stove, ready to be served any time. Plus, a big steaming dish of chili or ratatouille can help you feel safe, warm, and cared for on a cold winter's night. So make up a favorite brumal olio — and encourage your friends to come on by. Ask them to bring along a beverage, a dessert, cheese and crackers — and insist they bring along at least one single person (preferably someone you haven't met yet). Even if you don't meet the love of your life that way, it'll be nice to have a roomful of warm people to help you get through the winter.

8. You could also advertise for a "winter boyfriend" on Craigslist. Perhaps. If you dare. And if you do, you'll have to let us know how that works out.

Do you have any good winter dating tips?