A Singles Guide to Survive & Thrive During The Holidays

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Holiday Lights Cuddle

’Tis the season…to get stressed about dating. Should you bring someone to the holiday party? When’s the right time to meet the parents? Will you be kissing your date or your dog on New Year’s Eve? Never fear. The League’s resident dating coaches Connell Barrett and Cherlyn Chong have you covered. 

First Things First: What To Wear

Red has long been associated with power, passion, and desire. So gents, sexy up a date by wearing a red shirt or a red tie. It’s been proven that women perceive men who wear red as more attractive and enticing. The color has also been the top choice of women who want to turn heads…and hearts. And don’t go for a conservative dark red either, go all out and make it HOT. It’s the holidays, make it count!

On the other hand, gold is a great color that alludes charm, elegance, and confidence. Gents, use it to accent your outfit in the form of a watch, cufflinks, or a simple metal bracelet. Ladies, wear a shimmering gold top or dress to add a level of sophistication and your date will feel like he’s the luckiest man in the room.

Going Plus-One At Your Holiday Office Party

Feel free to bring a date to your office party—it’s a chance to further strengthen the connection you created on the first date or two. Humans are social animals, naturally drawn to those who are well-liked by others. When they see your boss and officemates treating you well, they’ll be impressed. Social proof is a big turn-on. Just make sure the party is a plus-one situation. Oh, and go easy on the sherry eggnog. Getting buzzed is fine,  but fellows, draping mistletoe from your belt-buckle, not so much.

Will Your New Love Interest Last Through the New Year?

This could be for anyone—but ladies, listen in! One main issue people have is how to tell if the new person you’re dating is the more serious type or has been simply swept away by cuffing season. Here’s my rule: If they have asked you to a holiday work party or a family gathering, where you’ll be introduced to the people in their life—AND they have asked you out on a separate, cozier date—you’ve got a good thing going. And if they’ve already asked you out for New Year’s Eve, that’s a sure sign that you’re going to be dating well into 2020.

Meeting The Family

If you’re dating casually, don’t meet the family just yet. This goes for both women and men. If you haven’t discussed relationship goals yet—don’t know if the person you’re dating is The One or is just wanting to have fun—it’s best to not meet the family this year. You don’t want to be asked probing questions from their mom or feel any pressure to take this any further than you’re ready for. It’s OK to take it slow, even during the holidays. Just make sure that the other person is aware of it too.

If you and your love interest are getting more serious during this season, you may be meeting a new partner’s parents for the first time. To make a good first impression, follow the old saw: To be interesting, be interested. Be sure to get some advanced intel about Mom & Dad, and ask them about their recent trip to Tulum or their love of skiing. Let them open up about their passions—it makes for way better conversation than small talk. For double bonus points, tell your date’s folks something specific that you love about their kid. Parents love knowing that their baby is with someone who appreciates them.

Clarify Your Dating Outcome

You’re the goal-oriented type—an achiever. (Of course you are! You’re in The League.) Odds are, you set clear outcomes for your career, your finances and your fitness, yet your romantic goals are fuzzier (“I’ll meet someone when the time is right…”). So write down an exciting, measurable outcome you want for your love life, and choose a target date. The further away your date of completion, the bolder your vision can be. Examples: “By Christmas, I will have had at least one date with someone I really connect with,” “I want to attend a New Year’s Eve party with a person I see as a potential partner—and be kissing them when the ball drops,” or “On Valentine’s Day, I’d like to have a romantic dinner with someone I’m dating exclusively.”

Reread your dating outcome daily to keep your eyes on the prize. A clear, compelling goal will fuel you to take the actions that will make your vision a reality. If you don’t achieve your goal by the target date, don’t sweat it. Simply reassess what worked and what didn’t and choose a new dating outcome or a new target date. 

Ringing In A New Year

For the Gentlemen: “Approach” New Year’s the Right Way. In the Dating App Age, approaching has become a lost art. If you’re still single on the cusp of 2020, know that New Year’s Eve is the best night of the year to go out and meet people the old-fashioned way—by walking up and talking (What a concept!). It’s the night when most everyone is in a festive, approachable mood, and a simple “Happy New Year” works as well as any pickup line. So snag an invite to a well-populated party and mingle. And if you’re never sure when to go for that first kiss…on New Year’s Eve, a built-in window opens at midnight. (10, 9, 8, 7…)

For the Ladies: No New Year’s Eve date by Christmas? Plan a Ladies’ Night Out! New Year’s Eve is a big thing and you don’t want to be holding out till the 30th for the chance of a date. Get a bunch of your single girlfriends together and take back the night! If you do get asked out, simply plan the date around the evening out. Your friends were there first, don’t ditch them just because you have romantic plans with someone you just met. Men respect a woman who knows her priorities, after all. 😉 Also, your date will know that he has to up his game—you do have a life and you’re living it regardless of him!

Cherlyn Chong is a breakup recovery and dating coach for high-achieving professional women who want to get over their exes and find love again. Find out more at StepsToHappyness.com or @stepstohappyness on Instagram. Connell Barrett is a dating coach for men and the founder of DatingTransformation.com. Follow him on Instagram at @datingtransformation.

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