Dapper vs. Dud: Holiday Dating Do’s & Don’ts

Are you a smooth talking turkey or a stiff-lipped Scrooge? Professional Matchmakers and dating experts weigh-in on how to charm even the most grumpy of Grinches...

Are you a smooth talking turkey or a stiff-lipped Scrooge? Professional Matchmakers and dating experts weigh-in on how to charm even the most grumpy of Grinches!

Dating expert, Evyenia Trembois, speaks to this season’s singles:

DO embrace the uniquely specific (okay, sometimes cheesy) events that come around during the holiday season. Did that new guy you’re seeing invite you to his work Christmas party? Sure, it might feel a little early in the relationship to accompany him to a work event, but the holiday season has different rules. If you’re enjoying getting to know the person, embrace the holiday festivities, drink the eggnog and have a good time! No need to over-think.

DON’T use the cold weather, and desire for a New Year’s date as an excuse to lower your standards. It’s better to go to that party alone — who know’s, you might even meet someone there — than to bring along a lukewarm date just for the sake of having one. Dating around the holidays can feel intense enough as it is, so don’t waste anyone’s time.

DO continue going on first dates during the holiday season.

Once Thanksgiving rolls around, single people often put dating on the back burner until the New Year sets in. Don’t let the holidays stop you from continuing to meet new people! If you look past the hectic travel days and scrambling for last minute gifts, December is a cozy, warm, and hopeful time of year — making it an ideal time to date. 

DON’T buy a Christmas gift for that girl you’ve only been on 2 dates with but really, really like. She didn’t get you anything.

DO Take advantage of the holiday season by mixing it up with holiday date ideas! Check out the best places to see holiday light displays (most cities have neighborhoods that go all-out), carol singing, or any fun holiday-themed local activities.  

Professional Matchmaker & Dating Expert, Melissa Rogers, says

DON’T stress out about being “alone” during the holidays! If you’re single, use it as a time to curl up with your favorite holiday flick and nurse a glass of hot cocoa (or wine). 

DON’T use the holidays as an excuse to eat your weight in sugar. A small piece of Aunt Meg’s chocolate brownie bark isn’t going to break the wellness bank, but one of everything on the dessert bar might. Yes, you’ll feel heavy and bloated, but you’re emotional state will also not thank you for the sugar-low after the rush.

Nurture confidence and self-love before, during and after the holidays!

DO invite a date to see a local holidazzle parade. It’ll be a great time to get a little closer and test chemistry with some snowy snuggles. 

DO host a party with a theme! Ugly sweaters might be overdone, but how fun would it be to do a retro 50’s style holiday party or a “Ghosts of Christmas Past” theme? Show off your hosting skills and maybe catch the eye of a lucky party goer. 

DO enjoy the holidays whether you’re alone or attached. There is always something to be thankful for. 

Professional Matchmaker and Heartalytics writer, Cora Boyd, addresses those who are newly coupled:  

The holidays are a charged time for dating. What with the societal pressure to show you’re boo’d up, the heightened desire for someone to snuggle while drinking hot chocolate, and the copious amounts of hot toddies available, it can be hard to keep a clear mind about your budding romance.

The pressure is on: will you invite each other to holiday parties? Will you meet each other’s families? Will you kiss when the ball drops?

Although it might feel overwhelming to navigate how your new relationship will fare during the most intimate time of year, the holidays present a great opportunity to gage your own intentions, your partner’s intentions, and potentially up-level your relationship.  

In order to not push your new relationship to the point of combustion, it is imperative that you meet your relationship where it’s at currently, while being mindful of where you want it to go. If you’ve only been dating a month, it might be a little hasty to invite your boo thang to your uncle’s eggnog extravaganza.

If, however, you’re ready to take your relationship to the next level, tell Uncle Kenny to pour it up. Invitations during the holiday season are more symbolic of your intentions than any other time of year, so know that your decision to spend (or not spend) this highly coveted time with someone sends a message. (This is coming from a woman who once went on a second date on Valentine’s Day. It was awkward). If you’re unsure, test the waters by inviting your guy/gal to a friend’s holiday party rather than a family one. And if you’re sure, grande gesture away! You won’t know unless you ask.

Professional Matchmaker Tania Abramova agrees that the holidays up-the-ante:

The holiday season is a festive time — from twinkling lights, to warm beverages, and countless celebrations. But for those of us in the dating world, this time of the year may increase the pressure on budding romances.

Family face-time can often lead to those dreaded relationship pusher questions (are you seeing anyone?). Naturally, we long to share this special time with a significant other. Holiday parties can also have us wondering how soon is too soon for your new romantic interest to become a plus-one.

I recommend slowing down and setting reasonable expectations for yourself and for your partner (if in a new relationship).

My go-to tips:

  1. It’s OK if communication falters
    The holidays are a busy time for everyone. Haven’t heard from your new guy/gal in a couple of days? Don’t panic. Before losing your gingerbread cookies, consider that they’re simply wrapped-up (pun intended) in the chaos of the season. Give others space to focus on their friends and family. 
  2. Create holiday traditions together
    Instead of integrating your new partner too quickly into family and friend get-togethers, consider more low-key activities that focus on the two of you — trim the tree, make eggnog, or shop for ugly sweaters for your respective parties. Intimate celebrations can reduce the pressure while bringing you closer together.  
  3. Presents or no presents
    While we all know the holidays aren’t just about getting that sweater you saw at Bloomingdale’s, gift-giving is a tradition that’s sticking around. In new relationships, the question of whether or not to do a gift exchange is tricky. If you feel comfortable, I recommend surfacing the topic directly — would you like to swap gifts or keep it casual? Otherwise, go small. An ornament or homemade cookies can go a long way. The goal is to make your new flame feel appreciated, but not overwhelmed. 

Professional Matchmaker & Dating Coach, Sophy Singer, agrees with the other experts:

If you just started dating someone (it’s been less than 3-4 dates within a month), don’t rush to invite him/her to holiday parties with close friends, family, and/or co-workers. Some people view meeting one another’s friends and family as a sign of taking the relationship to the next level. This could potentially create stress or scare someone off, who’s more of a “slow burn” in the first month of dating.  

Another gift warning (and idea)!

If you’re in the early stages of dating (less than 2 months), don’t spend your entire holiday bonus on a present for him/her. I agree with Tania that the best way to handle this is to discuss it directly. Though, I recommend making the conversation “merry!” Try introducing the idea of a fun, little gift exchange or game for your next date. 

Something like: “Let’s see which one of us can find the most ridiculous gift for one another for under $20!” 

Professional Matchmaker & Dating Expert, Remy Boyd, provides several important reminders:

DON’T force your holiday traditions, festivities or expectations onto others. Everyone celebrates the holidays in their own special way!

DO keep the holiday attire to a classy minimum. Ugly sweaters and Santa hats are cute, but generally speaking they’re not sexy. Keep your date attire warm, relaxed and on-trend with classic red sweaters for guys, and comfy accentuated dresses, skirts or slacks for the ladies. A festive scarf, broach or ear muffs show you’re in the holiday spirit without looking like you escaped from the North Pole!

DO be grateful for the love you have during the holidays. If you’re having a tough time with your partner, rather than call it quits (due to pressure or stress), focus on good will, togetherness and compassion — the major themes of the holiday season. Give that extra effort! Kiss under the mistletoe, enjoy eggnog and cookies in front of the fire place, cuddle on the couch and wish upon a star! 

DON’T feel like a loser if you’re single. View the happy couples, love and family bonding you’re seeing everywhere as inspiration. Allowing the holiday blues to creep-in is a non-starter. Volunteer in your local community, help a neighbor or call a friend you know you won’t see during the season. Find something, anything, that brings you joy and be happy to have it in your life. 

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