9 Holiday Dating Do’s and Don’ts According to Matchmakers

Some say the holidays are the most wonderful time of year, and it’s hard to argue with that sentiment. From the twinkly lights strung around Christmas trees to the warm mugs overflowing with hot cocoa and marshmallows, there’s certainly something so very inviting and cozy about the holiday season. 

However, all that holiday magic often brings some big expectations when it comes to the love department, making it difficult to know how to navigate the dating world during the remaining weeks of the year. 

To help, we’ve listed our top holiday dating do’s and don’ts. No matter if you’re single with no prospects in sight, dating here and there, or recently coupled up, our holiday dating advice is here to see you through the new year. 

1. Don’t Put Too Much Pressure on Yourself

When it comes to the holidays, we get it; there’s a lot of pressure. Maybe you’re tired of showing up to your company holiday party without a date or sick of explaining to your Great Aunt Lucy that you’re still not married. Whether you want to avoid broadcasting your singledom to everyone or simply want someone special to kiss on New Year’s Eve, try not to let holiday expectations get to your head.  

If you’re already seeing someone, great! Have fun together this season, and don’t allow the implications of a holiday romance to make you act differently or expect more out of your relationship. And if you’re still single, continue to go on dates and enjoy this time without pressuring yourself to find someone simply for the sake of having a New Year’s Eve kiss.  

2. Do Turn Holiday Traditions into Date Ideas

It’s easy to get into a dating rut, going to the same date spots every night or doing the same things every weekend together. But when you’re dating during the holidays, it’s the perfect excuse to switch things up. 

For this one, our holiday dating advice involves using this festive season to your advantage! Instead of going to that same old restaurant you go to every Friday night, why not check out the holiday parade? Or, rather than watching a movie on a Sunday afternoon, try your hand at baking holiday cookies together! From volunteering at a local toy drive to decorating the Christmas tree together, there are so many fun winter date ideas to enjoy with your partner this season.  

3. Don’t Forget about Me-Time

If you’re dating during the holidays, that often means twice the work parties, twice the family gatherings, twice the Secret Santa events, and twice the cookie-baking contests! Yes, that likely means twice the fun, but it also means you’ll have less time to yourself this holiday season. 

Even if you’re absolutely head over heels with the person you’re dating, it’s important to set aside time for yourself this holiday season. Give yourself breathing room and do some things on your own, whether that’s hitting up a holiday party solo or spending the afternoon reading a book by yourself. By attending to your self-care routines and giving yourself space, you’ll be happier, more refreshed, and empowered to celebrate the holidays when you are together. 

4. Do Accept All Those Holiday Invitations

If you’re not in an exclusive relationship, then meeting new people at holiday gatherings is fair game! After all, everyone seems to be getting together during this time of year, from your neighbors in your apartment to best friends from college. With all these invitations coming your way, you’re bound to meet some other singles who are ready to mingle, so prioritize these holiday events and be open to putting yourself out there. 

5. Don’t Get Wrapped up in the Stress of Gift-Giving

Gift-giving can be a major source of stress during this time of year. So, if you want our holiday dating advice, we recommend going easy on the presents. 

If you’re new to the relationship, consider having a discussion about the expectations of gifts. You could place a cap on the amount of money you spend on each other, or you could even think of a joint present or experience you could get each other instead. Now, if you’ve only been on a date or two, a gift probably isn’t necessary, but if you insist, go for something small, thoughtful, and inexpensive to avoid making them uncomfortable. 

6. Do Go Slow

Watching sappy holiday movies and seeing your siblings and cousins all paired up for family gatherings can make you wish you were further along in your relationship. While it might feel like there’s holiday romance around every corner, don’t let that impact the pace of your relationship. 

For example, if you’ve only been on a few dates with someone, don’t feel obligated to bring them to your Friendsgiving, as that might imply you want to be exclusive, even if you’re not emotionally there yet. Or, if you fly home to see your family each December, avoid inviting your partner to join you unless you’re 100% ready to introduce them to your parents. 

7. Don’t Forget the Holidays are Just a Few Short Weeks

A lot of people dread the holidays, especially if they’re single or not in a serious relationship yet. But just because you don’t see a ring box-shaped gift under the Christmas tree or aren’t curled up around the fireplace with a significant other doesn’t mean you should mope around for the next two months! 

The holidays are really just a short stint that is going to come and go before you know it. Instead of letting expectations of holiday romance get to you, try to enjoy these final months of the year as you look forward to all the excitement and new love prospects 2024 will bring. 

8. Do Focus on Others

When you’re dating during the holidays, it’s easy to get wrapped up in all the fuss, from attending holiday parties together to finding the perfect gifts for each other. However, it’s also important to step back and remember that giving back is an important part of the holidays. Whether you’ve just started seeing someone or have been dating someone for a few months now, consider ways in which you can volunteer your time or money to your local community together. For example, you could help host a food drive, donate to a toy drive, volunteer at the soup kitchen, or even join a charity event. 

When you and your partner spend time helping others during the holidays, you just might find yourselves building a stronger, more fulfilling, and purposeful relationship in which you share common goals. 

9. Don’t Go Looking for Love in the Wrong Places

As for our final piece of holiday dating advice, don’t resort back to an ex or past hookup for the sake of feeling less lonely during this time of year. Trust us; no good is going to come from inviting your ex to your company party or drinking spiked eggnog with that fling from last summer. Even if the thought of a holiday romance with a past lover sounds nice while you’re hanging stockings or singing along to Christmas carols together, those warm and fuzzy feelings are fleeting. Remember, you moved on from them for a reason, and going back to them during the holidays is only going to set you back as you open old wounds and complicate your healing process. 

Instead of going backward, surround yourself with your friends and family and embrace love and joy in other ways this holiday season!