Ah, the holidays—when everything is draped in twinkling lights, the smell of cinnamon fills the air, and Hallmark movies set completely unrealistic expectations for love. It’s also the time of year when your feelings might just feel a little extra... heightened. Maybe it’s the cozy vibes, maybe it’s the mulled wine, or maybe it’s the fact that your partner looks really good in a chunky knit sweater. Whatever the reason, you’re wondering: Is now the right time to drop the L-word?

Here’s the thing—saying “I love you” for the first time is a big deal. It’s like putting the star on top of your relationship’s Christmas tree. You want to get it right, not just because the holidays are right around the corner, but because those three little words can shift the dynamic of your relationship in the most beautiful way. So, grab a glass of wine, and let’s dive into the do’s and the don’ts of saying ‘I Love You’…

Do: Make Sure It’s Genuine

First things first: love isn’t a race, and it’s definitely not a competition. You don’t need to rush into saying “I love you” just because it feels like everyone around you is doing it. Saying those three words should be something that feels natural, not forced. If you’re already feeling it, great! But make sure you say it because it feels right—not just because it’s been a certain amount of time or because you’re trying to check off a holiday box.

Don’t: Say It Just to ‘Seal the Deal’

There’s something about the holidays that makes everything feel more intense, like the magic of Christmas has some kind of love spell attached. We’re surrounded by cozy moments, glittering lights, and everyone around us seems to be in a happily-ever-after mood. While it’s easy to think that the holidays are the perfect time to drop the “L-bomb,” don’t let the season pressure you into saying it before you’re ready. If you’re not there yet, that’s okay. Don’t feel like you have to say it just to match the Hallmark movie vibe. Love is about vulnerability, not ticking off a box on your holiday to-do list.

Do: Pick a Moment That Feels Right

The perfect moment to say “I love you” isn’t always a grand gesture—it could be something as simple as laughing together over burnt cookies or walking hand-in-hand through a snowy park. The key is to choose a time when you feel connected and present. Those cozy, intimate moments are when you’re most in tune with each other, and they’re often when the feelings just naturally bubble up. If the words “I love you” come out in that moment, it’ll feel special and true, not rushed or forced.

Don’t: Overthink It—Let the Moment Happen Naturally

At the end of the day, don’t overthink the timing. Whether it’s before the holidays or halfway through the year, love doesn’t follow a calendar. Let the words come naturally when you feel comfortable and sure. If they’re meant to be said before the holidays, they will be. And if not? That’s perfectly fine, too. It’s about enjoying the ride, building a connection, and letting your relationship grow at its own pace.

Do: Watch for Signs from Them Too

It’s not just about when you’re ready. If your partner is someone who values the moment as much as you do, you’ll probably see signs that they’re ready to say it too. Have they been dropping little hints? Talking about the future, and including you in it? When your conversations start turning toward long-term dreams—like where you see yourselves in five years, or who you want to spend the holidays with—those are great signs that you might be on the same page about your feelings.

What If They Don’t Say It Back?

Okay, let’s address the tinsel-covered elephant in the room. What if you say it and they don’t say it back? First, don’t panic. Love is a journey, not a synchronized dance. If they’re not ready to say it, it doesn’t mean they don’t care deeply about you—it might just mean they need a little more time to catch up. And hey, at least you were brave enough to say it. That’s a win in itself.

Saying “I love you” is a big deal, but it doesn’t have to come with a perfectly orchestrated moment or a pre-determined timeline. If you’re feeling it and the holidays feel like the right time, go for it! And if you’re not there yet, that’s okay too. Love doesn’t follow a calendar—it follows your heart.

Whatever you decide, just know that the holidays are about connection, gratitude, and making memories. Whether you’re saying “I love you” for the first time or just enjoying the moment, the best gift you can give is your presence. Because there’s no “perfect” way, but there’s always the right way for you. Until next time x

HJF for First Round’s On Me