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Tips for Holiday Dating

Can you date successfully during the holidays?

Goskova Tatiana/Shutterstock
Source: Goskova Tatiana/Shutterstock

For most people, most of the time, dating is a lot of fun—especially if you’re dating someone new that you really like. But it can also be stressful, what with wondering if this new person is your soul mate or just great in bed. And when the holidays roll around with stresses of their own, the mix can become a wee bit combustible, especially if you and your new paramour don’t have a plan for how to handle the holidays.

The first and most important thing you and your dating partner can do if you want your relationship (and your sanity) to survive the holiday season is to have a light but meaningful conversation in which you set some ground rules for things like gifts, social events, finding time to be together romantically, and having hot holiday sex (if sex is currently on the table in your relationship).


“One time I broke up with a woman I really liked because I didn’t know what to get her for Christmas.”
—Stephen, 42

OK, you’re dating a slice of total hotness who’s also really fun, but your relationship is still new and you have no idea what to give as a holiday gift. Do you get your new steady something big and romantic, or do you keep things low-key? Are you worried that if you buy too much of a gift, your dating partner might get spooked, and if you buy too small of a gift, he or she might feel slighted? How will it feel if your dating partner gives you too much or too little? And what if your gifts don’t match up in quality/expense? So yeah, gifts can be a serious holiday dilemma. There is, however, a solution. Together, you can set a limit on how much to spend. (If your relationship is really new, I suggest keeping the outlay modest with gifts geared more toward fun than romance—tickets to a show, for instance.) You might also turn buying each other’s gift into a date. After all, shopping together and letting each other say yes or no to certain items is a great way to learn about each other and grow closer. Plus, you know that whatever you give will be appreciated, because the other person has already indicated that he or she likes it. In any case, limit yourselves to one gift and one gift only, and if you’ve set a price limit, which I strongly recommend for new relationships, stick to it.

Parties and Events

“Two years ago, my second date with a man was midnight mass, Christmas Eve, with his entire family, including his parents, kids, grandkids, and even his ex-wife. Yuck. There was no third date.”
—Lee Anne, 55

There are a million different types of holiday parties, events, and gatherings, and you and your dating partner will probably want to attend some but maybe not all of these together. Parties with mutual friends are easy: You both go to those. Other soirees can be a bit more complicated. For instance, office/work parties often suggest that employees bring a spouse or significant other. If you take a date to such an event, your coworkers will naturally assume the relationship is serious, and so will your date unless the two of you have clarified, prior to the event, where you stand as a couple. So if you’re dating casually but still want to go to these parties together for mutual support and because you have a good time, that’s totally cool, as long as you are both crystal clear on your casual dating status. Events with family are even tougher. After all, meeting family is often the acid test for a relationship. My suggestion is that if you’re dating casually but think things might eventually get serious, it’s OK to attend a family event together, but make sure your mother knows that things are still casual. Otherwise, she might hear phantom wedding bells.


“The stress of the holidays can be a real turn off sometimes. I mean, after a full day of work followed by some frenzied shopping and then a party, do I really have enough energy left for sex?”
—Jameson, 28

The holidays are incredibly busy with all sorts of work, family, and friendship commitments. As such, it can be difficult to find time for romance. However, if you and your dating partner plan a few dates well in advance, you can spend some quality time together (that you’ll find yourself looking forward to), perhaps helping each other de-stress from the not-so-quality time you’ve had at the overcrowded mall, the grocery store, and lunching with your neurotic sibling. I suggest you keep these dates simple—a nice dinner out and a carriage ride through the park, for instance. If being sexual is part of your relationship, then plan a night to cue up the Barry White, light scented candles, and give each other a hand or foot massage. (Trust me on the massage idea!) Or maybe the two of you could take a bubble bath and then dress up like Santa and his favorite sexy elf. Or whatever. Don’t be afraid to get creative. Whatever you decide to do, try to also spend a few moments telling each other what and how you are feeling about life, the holidays, and spending time together. If you do this, you’ll find that these intimate conversational moments, more than any actual sex (no matter how hot), are a wonderful way to relax, connect, and slowly but steadily develop a more meaningful relationship.

Robert Weiss LCSW, CSAT-S is Senior Vice President of National Clinical Development for Elements Behavioral Health, creating and overseeing addiction and mental health treatment programs for more than a dozen high-end treatment facilities, including Promises Treatment Centers in Malibu, The Ranch in rural Tennessee, and The Right Step in Texas. He is the author of several highly regarded books, including “Sex Addiction 101: A Basic Guide to Healing from Sex, Porn, and Love Addiction” and a forthcoming volume about surviving relationship infidelity, “Out of the Doghouse: A Step-by-Step Relationship-Saving Guide for Men Caught Cheating.” For more information please visit his website at or follow him on Twitter, @RobWeissMSW.

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