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Holiday Gift-Giving When You’re Dating Someone New: How Not to Make it Weird

Is this even a possibility? Not making gift-giving at holiday time weird when you’re dating someone new or new-ish? No, not at all. If you choose your gifts right, that is. And get rid of some of the expectations you may have around gift-giving. 

It’s understandable how holiday gift-giving can become a nail-biting event. No one wants to be standing there with a gift that’s not in line price-wise with the one they’re receiving. The same goes for giving a gift that, although inexpensive, imputes depth to a relationship that may not be there just yet, at least for the person you’re giving it to.  

That’s why I’ve come up with a few tips to avoid feeling like you’re stuck in that wacky dream where you show up to work or class naked. After all, holiday gift-giving should be something you look forward to rather than fear

Get on the same page about gifts before the holidays arrive. 

A lot of the angst you may feel around holiday time surrounds whether or not you and the person you’re dating are on the same page. That’s is why I suggest having a conversation about exchanging gifts before the holidays, so you’re both on the same page about your expectations. 

Now, if it’s September and you’ve just started dating, it’s not time to project about what you’re giving each other. However, if your relationship appears to be going well and is on track to continue through the holiday season, feel free to bring up the subject casually around Thanksgiving.  

That could mean anything from suggesting to stick to a specific budget or price range to making a suggestion about the type of gifts you will be exchanging that you and, hopefully, they will be comfortable with. The point is you set up a plan.    

It may not sound romantic at first, but depending on how you position the conversation, you could make it so. First off, you can plan an activity to celebrate the holidays, such as attending a show or concert. Maybe one of you pays for the tickets, the other dinner.  

Or perhaps you propose the idea of setting aside a time to bake or cook your favorite holiday dishes together, watch a movie, and exchange something small? Or if you’re both on board, what about creating your holiday gifts? 

Buy two gifts at two different price points. 

So, you like surprises and aren’t comfortable having a discussion about holiday gift-giving in advance. But you absolutely have no idea what to spend. 

In this case, my suggestion is to buy two gifts, one at a lower price point and one at a little more significant price point but still commensurate with the length and depth of your relationship. For the former, I would suggest gifts such as scarves, slippers, pajamas, and books (this can include journals to write in). For the latter, I would recommend some type of electronic item, perfume or cologne, or a more luxurious clothing accessory. 

But here’s the catch: start out with the small gift. Then, based on what the person you’re dating gives you, decide whether or not you want to add the second part of your gift.  

The second gift should be nearby, in a drawer or a closet, for example. If you’re not home, leave it in the trunk of your car out of sight. You can always excuse yourself to get it. This way, you can keep your gifts around the same price point without making yourself or the person you’re dating uncomfortable. 

Decide beforehand there will be no weirdness about gifts. 

This is the option where you decide you’re going to let the situation unfold as it will. You tell yourself in advance that even if you give a much more expensive gift than the one you receive, you’re giving the gift you want because it expresses how you feel.  

The same goes for giving a less expensive gift because that’s what you can afford even though you wish you could give more, and the person you’re dating does give more. So be it. 

You’re confident in your own skin (and with the gift you choose to give) to not care about any imbalances in this particular instance. You see your relationship for what it is and know money doesn’t reflect the thought or time that can go into a gift. You also understand that a holiday gift is but one of the many ways people express how much they care about each other.  

Most importantly, you realize that making things weird over something as insignificant as a holiday gift early on in your relationship could mean the demise of your relationship. And that’s something you’re not willing to risk because having a quality partner in your life is in itself the best gift of all.