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Home > Dating Advice > Dating Someone New Around The Holidays: How To Approach It

Dating Someone New Around The Holidays: How To Approach It

Happy couple smiling and dancing in Christmas setting while dating during the holidays.

Dating someone new around the holidays can be nerve-wracking. There’s a lot to think about. Will they expect you to celebrate with them? What do you do about gifts? And is it too early to spend money on each other?

Luckily, you’re not the first person to feel this way. Whether you’ve hooked up with someone new for the winter months or finally gotten together with your long-term crush, one of the most important factors in dating someone new around the holidays is figuring out what the person in question is like. Are you dating someone who’s excited to celebrate? Or do they keep things low-key until the new year? 

No two situations are the same, and expectations may change from person to person. That said, here are some general ways on how to approach the situation.

What to Think About When Dating Someone New Around the Holidays

Openly ask them if they have holiday plans

This is a great question to ask when you’re dating someone new around the holidays. It’s not a red flag to want to try and plan out your schedule around theirs. Keep in mind, you aren’t at a stage to control their plans. If they want to fly back home to see their parents, it’s probably too early to invite you just yet. 

You should appreciate a partner who doesn’t want to rush into that stage, especially since things can often get busy around the holidays. If you’re still together next year, you can probably expect things to be different.

Ask them if they’re willing to exchange gifts

This is the best way to know where their mind is at when it comes to presents. If they say money is tight, believe them and don’t push too far. Remember, there’re plenty of other gift-giving holidays the two of you can celebrate in the future. 

By disrespecting the plan they set — even if it’s in good spirit — you’re sending off a bad message that you don’t take boundaries seriously. If you absolutely have the urge to give something, make them a music mix or another fun craft that doesn’t cost money. Cards are also a great way to share how you feel.

If you absolutely have the urge to give something, get creative and organize a gift that doesn’t cost money. Try out a platform like Zoosk Great Dates, for example, and whisk your new squeeze off on a romantic virtual city tour.

Whether you choose a guided trip around the ancient architecture of Athens or a romantic wine tasting tour in Naples, virtual dates like these are thoughtful, meaningful gifts that can really show your date how you feel.

Doing a virtual date over the holidays is also a good way to take the pressure off from having to meet each other’s families and be in the same place at the same time, at least in the early days!

If you do exchange gifts, decide on a price range together

It’s not tacky to say something like, “let’s keep gifts around $50.” That way, you’re making sure nobody is disappointed. Dating someone new around the holidays comes with enough challenges as is, so try to make things easy when you can. 

Remember that gift-giving can send a message. “In early dating, gift-giving is usually more of a transaction and reciprocal exchange,” writes Psychology Today. “At this stage, men, in particular, might be motivated to buy lavish gifts to escalate the relationship.” Don’t scare them off — just go for something sweet and thoughtful.

Be respectful towards family

If you get the chance to meet their family, that means your new partner is serious about this relationship. If you’re also looking for something long-term, you’re in luck. Remember, first impressions mean everything. Try to approach the gathering casually and in a friendly manner. 

Don’t be overprotective of your date, and make sure the hosts know you’re happy to be there. Want to make an even bigger impression? Bring over a bottle of wine, or offer to bring a side dish or dessert.

Be flexible with plans

One of the big truths about dating someone new around the holidays is that their schedule might be packed. Remember, this is the season to be busy. If you two weren’t looking for love but found each other, it makes sense that they filled their calendar with other obligations ahead of time. 

It’s your job to be understanding and not resent your partner if you’re feeling a little lonely. Again, by this time next year, the two of you will be more established.

Communicate about everything

Communication is the key to a good relationship. If the two of you don’t talk in person, it makes sense for plans to be jumped or misunderstood.

Questions like, “how should I dress for dinner at your aunt’s house?” to “what’s the typical Christmas Day schedule at your mom’s house?” aren’t overwhelming, and are important to make sure the two of you are on the same page. If you feel silly talking to your partner, that’s an issue worth working on in the future if you’re hoping to date for a while.

If they celebrate a different holiday, consider learning more about it

Have you always been curious about Hanukkah or Kwanzaa? Now’s the time to learn more about it. Different cultural events are important to celebrate, but make sure to be considerate and take it all in. Don’t try to lead events, or Google how you believe they should be run. In this situation, you’re the student.

While dating someone new around the holidays can be a bit intimidating, it’s also a great time to fall in love. Winter is a lovely time to be dating, with things like playing in the snow and drinking hot chocolate by the fire being two wonderful ways to develop strong feelings for each other. If the two of you can survive the holidays unscathed, we’re pretty sure you can survive anything.

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