10 Tips for Avoiding Holiday Dating Disasters

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I know, I know: It's not even Halloween yet and already I'm talking about the holidays. You're thinking: Please, gag me with a turkey baster.

But the fact is I've already got the cold-weather festivities on the brain. And not just because the pumpkin butter I've been having on my morning toast is arousing Thanksgiving reveries, a la Proust's madeleine. More significantly, Mr. Cup-of-Tea and I have already started discussing the holidays.

I have been wondering what I want in terms of participation: If we're still together in December, will I be happier if he hangs out with my family on December 25 — or will it be less stressful for both of us if we simply agree to do the holidays apart?

With all this in mind, I decided to give you some tips on how to make the holidays less romantically stressful.

If you are single:

1. If you find yourself unattached in November, rejoice!

When I first mentioned that I was going to be talking about tips to help daters survive the holidays, a bunch of readers said, "Avoid dating till January!" The holidays stress us out — there's so much to do, shopping sucks, it's cold, and any existing family tensions are exacerbated — so trying to get a new relationship started is the last thing you want to add to your to-do list, especially because there are so many holiday minefields that could blow the fragile little romance to smithereens.

If you have just started dating someone:

2. Don't feel compelled to bring some new guy to your office party.

Office parties can be stressful and awkward for even the most graceful employees — and adding a new beau to the mix will just increase the pressure on you. Plus, a bunch of people standing around talking shop while getting drunk and doing karaoke is no outsider's idea of fun. He'll probably be relieved if you let him off the hook, explaining it'll be easier on both of you that way.

3. Similarly: Don't be offended if he doesn't bring you to his.

It goes both ways.

4. Think twice about casually inviting him to any family holiday party.

Don't tell yourself, "Oh, what the hell — why not kill two birds with one stone?" Introducing a new guy to anyone in your family automatically ups the ante, especially during the holiday season. Also, sometimes our families make us act not like our better selves, to say the least. You don't want a new guy to see you behaving childishly or peevishly. What's more, your relatives might be weird or annoying or simply not his speed. Your mother — whom everyone thinks you look so much like — may be aging very poorly, your father could be the kind of jackass no one would ever want to be in a restaurant with, and so on. So make sure he's seriously into you before easing him into your family.

If you're more serious:

5. Talk about the gift situation.

Not sure if you two are serious enough to buy each other gifts? Or feeling uncertain about how much to spend? Talk about it rather than tiptoeing around the issue. Ask if he thinks exchanging gifts would be fun — and, of course, tell him how you feel. If neither of you is making much money, agree to do something inexpensive, like going to a bookstore and buying each other a novel or a volume of poetry. You can also simply make each other presents, like a set of CDs (consisting of a cozy winter soundtrack or a sexy soundtrack). Or think about agreeing to donate to worthy organizations in lieu of a gift exchange.

6. Think "compromise" rather than "sacrifice."

Are you and your new boyfriend talking about how to split up the holidays? Does he want you to spend the holidays with his family members, while you want him to spend them with yours? If it's geographically possible, split the difference. Do Christmas Eve with his folks, and spend the day of the 25th with yours, or lunch with one clan and dinner with the other. Or consider doing Christmas with one tribe and New Year's (or Thanksgiving) with the other. If logistics are tricky, and neither of you wants to disappoint your family (or yourself!) by not seeing them over the holidays, simply agree to go your separate ways for the day — and do a special holiday dinner together, just the two of you, sometime before New Year's Eve.

7. Do some advance work.

If your boyfriend has pleasantly agreed to come to your Aunt Clara's house for some turkey, give him a sense of what he might be in for so he can prepare himself. If she's going to grill him about his job, alert him to her prying ways. Or, if you know an inquisition will make him miserable, ask Aunt C. if she will leave the peppering to the salad dressing. Let him know about anything he can do to earn easy brownie points. Perhaps Clara will love him forever if he brings her flowers, or if he compliments her on her needlepoint pillow that says, "Remember the reason for the season: Presents." Think ahead about the little things you can do to make the day more socially smooth for everyone. And if you'll be with his family, ask him if he has any tips for you to make a great impression.

8. Pay attention to his dietary preferences.

The guy you're dating is a vegetarian, and your grandmother thinks no meal is complete unless it features something that once mooed, snorted, or bleated? Bring along a Tofurkey and some vegan cookies. If he's the type who gets irritable when he's hungry — and you have a long drive to get to the relatives' place — bring some snacks in the car. If you both will be spending the night with the folks, and you know your parents don't drink coffee — and your boyfriend can't be human in the morning without his java — consider bringing along a French press and some ground coffee.

9. Pay attention to your own physical needs.

Do your best to get enough sleep and to make time for exercise, especially if it's important to you. The better you feel physically, the more likely you are to feel psychologically at ease, too.

No matter what:

10. Take it easy on the alcohol at all times.

People often think drinking will ease all tensions and make everyone jollier. Instead, it regularly disables people's manners, amplifies any underlying moodiness or resentment, and encourages them to do things that are ridiculous, inappropriate, or offensive. So have a glass of wine or two with dinner, but cut yourself off after that. And if the person you're dating has a tendency to overindulge, ask him to make an effort to keep himself in check. If he has trouble pacing himself, suggest that he commit to having two glasses of water — or three — for every alcoholic beverage.

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