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Should You Get Your Date a Holiday Gift? Ask Yourself These 5 Questions First!

Here’s the scenario: you met online, you just started dating and, now, it’s suddenly the holiday season. To gift or not to gift? That is the question!

Maybe you’re a couple dates in, or a couple months in. Perhaps you’ve already had “the talk” and determined that you’re exclusive. Whether you’ve been on three dates or thirty four, it can be tough to gauge when it’s appropriate to start exchanging gifts with someone who is still relatively new in your life. After all, if you misread it, the situation can get awkward fast.

For example, when I was in college, I gave the guy I’d been dating on-and-off for a few years a bottle of nice cologne and a mixed CD of romantic songs (hello, early 2000’s!) In return, he gifted me a half eaten bag of chocolate almonds that he unceremoniously tossed to me from the other end of the sofa. Soulmates we were not.

On the flipside, a few years ago I went on a few dates with a guy who insisted on dropping by my house to deliver my “Christmas present.” We barely knew each other at this point, but I’d gotten to know him enough to know that we weren’t a match. Also: cue major awkwardness.

Don’t let either of these happen to you! If you’re trying to figure out whether you should buy the person you’re dating a gift, here are a few questions to consider.

1. How long have you known each other?

Has it been months, a few weeks, or just a couple of dates? If you’ve been dating for a few months and you’ve made it clear that you’re exclusive, read no further – get yourself to the mall so you can find something special for your sweetheart. It doesn’t have to be anything big, just something thoughtful. For example, maybe you want to get them that book they mentioned they’re dying to read, or something else that they’ve eluded to in passing. Make the gift extra sweet by including a nice, handwritten card that expresses how much fun you’ve had getting to know them, along with any other personal touches that might be appropriate. One of the best gifts I ever received included a bunch of photo prints of our favorite Instagrams together.

2. Are things serious?

If it’s only a been a few weeks or even a few dates, this is where things get tricky. If you literally just met, holiday gifts generally aren’t required (in fact, as demonstrated above, giving them might be more awkward than anything.) However, if you’ve been dating for a few weeks to a month, it never hurts to do something nice for the other person. For example, gift them an experience you can enjoy together (like sports tickets, a night of live music or a bottle of wine) or bake them something tasty if they have a sweet tooth (some homemade cookies are almost always a surefire win!)

FYI, when in doubt, you can never go wrong with flowers. One of the best, lower-effort gifts I’ve ever received was a gorgeous blossoming cactus plant. Just saying.

3. Do you know what kinds of things they’re into?

So, you’ve determined that you’d like to buy the person you’re dating a little something something. Now what? If you want to avoid flowers or edible gifts, give them a gift that’s reflective of something topical you’ve discussed. For example, if they’ve mentioned how much they love cooking, DO consider giving them a fun cookbook or kitchen gadget (avocado-halfer anyone?) If you shared a really memorable meal together, see if you can purchase a jar of the restaurant’s signature sauce or their cookbook. If you’ve noticed your date is always complaining about how their hands get cold when they text, consider buying them a pair of smartphone compatible gloves. At the end of the day, anything that shows that you’ve been paying attention to what they’ve been telling you is a great way to show you care.

However, if they’ve shared with you that they want to lose a few pounds DON’T take this as an opportunity to give them a jumbo sized canister of Ultra Slim Quick Weight Loss Formula and a day pass to a gym. Unless of course, a breakup is on your holiday wish-list.

If you honestly can’t think of anything that they’ve mentioned recently, it could be that you just don’t know each other well enough yet. If this is the case, it’s better to stick to something neutral like flowers or wait on the gifting altogether.

4. Do they have any sensitivities?

Ask your date questions and listen so you can choose something appropriate. If they’re gluten-free or paleo, you don’t want to buy them a giant gingerbread house made of wheat-filled flour. If they don’t drink, that Jack Daniel’s gift set also isn’t appropriate. Pay attention and act accordingly.

5. Have you talked about it?

This may sound crazy, but you could just ask them how they feel about holiday presents. Instead of stressing, have an actual conversation. Perhaps you’ll decide to forgo gifts altogether or make plans to do something holiday-themed together, instead. Maybe you’ll decide to gift, but set a rigid price limit (for example, $20.) Either way, having the gift talk means never having to ask, “Should I really buy them this Hillary Clinton-shaped Chia Pet?”


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