Top 5 Tips for Dating During the Holidays

dating during the holidays

Santa is loading up his sleigh and frosty is spreading his jolly joy. It’s the holiday season, and while everyone else is filled with cheer, you’re stuck stressing about your new beau.

Starting a new relationship around the holiday season is always stressful. You’re faced with some tough, and possibly embarrassing decisions to make.

If this dilemma sounds familiar, then stick around because we’ve got the top 5 tips for dating during the holidays.

Read on so you can cut the stress and start enjoying your new relationship.

Giving Gifts

Let’s start off with one of the most difficult questions floating around the holiday dating scene: “do we exchange gifts?”

Ladies, before we dive into this we need to emphasize that all relationships are different and there is no one right answer. That being said, we do have a few tips to help you out.


First, get to know your partner. Just like in any other relationship, you’ll need to really get to know them before you go out in search of the perfect gift. Unlike every other relationship, though, you’re going to have to expedite this process – and fast.

A good way to get to know someone really fast is to play the question game. Cozy up by the fire with some wine and cheese snacks and take turns asking each other random questions. The fun part of the game is that you have to answer.

Take note of his answers as well as the questions that he asks you, these can be a huge indicator for what he thinks of you.

Tip: If you’re really new into the relationship and are concerned about the question game getting uncomfortable, change it up by setting a rule where if you don’t want to answer you have to take a shot or sip of wine.


Second, girl, just go with your gut. If you really want to give him a gift, go for it and be proud of it. We don’t recommend going for the extreme getaway vacation this early in the dating game, but two tickets to his favorite film or sports team can never hurt.

Just keep in mind that if you’re debating on gift giving, he probably is too, so don’t let yourself be disappointed if he doesn’t get you anything.


The last bit of gifting advice that we have is honesty. If you really want to develop a strong relationship, why not just ask if he’s going to get you something? Be bold and don’t be afraid of the awkwardness, you’ll either look back and laugh or you won’t even remember it in a few years time.

If you do choose to exchange gifts, don’t be afraid to set a price limit. One of the most awkward experiences is to give someone a cheap Christmas card only to have them give you a pricey pandora bracelet.

Just ask.

Tip: if you’re seriously stressing about a gift exchange and aren’t comfortable asking him yet, we’ve got the perfect solution. Attend a white elephant gift exchange party. This is an event where everyone buys one gift (usually under in a price bracket) and the gifts are traded and raffles off. Everyone leaves with a gift and there’s no awkwardness.

Talk About the Uncomfortable Subjects

We mentioned that you can avoid talking about the awkward subjects by taking a shot or two, but at some point, you’ll need to have these conversations. Tackling them now can help you avoid some awkwardness later.

After all, you wouldn’t want to take him to the family Christmas party only to find out he celebrates Hanukkah instead.

Couples that started dating in July have the luxury of taking their time before discussing things like religion, politics, or even how many kids each of you wants.

You and your new beau, on the other hand, don’t have that luxury.

You might choose to think of this as a good thing, though. Finding out if you agree on religion or children, or any of the big stuff can save you a lot of heartache down the road. It’s a terrible thing to find yourself caught between the love you have for your partner and your burning desire to (or to not) have children.

If you find out now that you don’t agree on some pretty big issues, you’ll have the opportunity to decide if you’re willing to accept it into your life or not before you fall in love.

Go Shopping Together
Going shopping together can help you get a sense of what each of your interests is. No matter how hard you try, there’s no way to avoid window shopping at the mall.

Keep your eye on your partner and he will show you what his interests are. Does he stop to look at the sports shops? Did he stare a little too long at an outfit that would look perfect on you for the -after- Christmas party?

Invite him to come along while you Christmas shop for your family and encourage him to get his Christmas shopping done as well. You might even have the chance to learn a little about his, and possibly your future, family.

Tip: if you’re really struggling on finding the perfect gift, suggest that you go shopping together for each other’s gift. Set a price range and let him pick out his own gift. This is a sure fire way to avoid any awkwardness at the gift exchange.

Have Fun Dating During the Holidays

All in all, the most important tip for dating during the holidays that we can offer is to just relax. Stressing too much over the small things can seriously put a damper on any new relationship.

After all, it’s Christmas.

Remember that if you’re stressed, so is your partner.

If you’re really hoping for a happy ending with your new beau, check out these 7 mistakes couples make early on.

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