Dear Anna,

I’ve (36-year-old female) been seeing a new guy (34) for about six weeks — we’ve been on six dates, things are going really well and there’s clearly mutual interest, but we haven’t had the “what are we” conversation yet. Now Valentine’s Day is coming up and I’m completely lost. Do I acknowledge it? Plan something? Ignore it entirely and pretend Feb. 14 is just a regular Saturday? I haven’t been single on Valentine’s Day in almost a decade, so I genuinely have no idea how to navigate this. We’re not a couple, but we’re clearly more than just casually dating. I don’t want to make things weird by going all-in on a holiday that’s basically designed for committed relationships, but I also don’t want to completely ignore it and seem like I don’t care. Is there a middle ground here, or do I just bring it up directly and ask what he’s thinking? — Valentine’s Day Virgin (Again)

Dear VDVA,

Welcome back to the singles-but-not-really-singles Valentine’s Day limbo. It’s a special kind of weirdness and you’re not alone in having no idea how to handle it.

Here’s the thing. What you should do on Valentine’s Day at the six-date mark depends almost entirely on what Valentine’s Day actually means to you — and to him. And those answers vary wildly from person to person.

Some people are genuinely into Valentine’s Day. They love the ritual of it, the excuse to be romantic, the heart-shaped everything. For them, a thoughtful acknowledgment early in dating feels exciting rather than scary. Others couldn’t care less — Feb. 14 is just another day with worse restaurant reservations and a sudden expectation to fake enthusiasm for swing dancing or sunset cruising. Some people see Valentine’s Day as a commitment landmine, a holiday that implies a level of seriousness they’re not ready to assign to a six-week situationship. And then there are those who simply see it as a good excuse for a nice dinner and a bottle of wine, no deeper meaning required.

So, which one are you? And more importantly, which one is he?

If you don’t know, find out ASAP. (More on that below.) Because if you’re both in the “nice dinner, no big deal” camp, then suggest plans and stop overthinking it. If you’re secretly hoping this turns into a big romantic gesture that clarifies where things are headed, you might be putting a lot of pressure on a holiday to do the emotional work that an actual conversation should be doing.

Generally speaking, six dates is firmly in the “acknowledge but don’t go too nuts” territory. This is (probably — again, to each their own Ferrero Rocher pyramid) not the moment for a fancy weekend away or a jewelry box. But you totally have enough history to send a casual, “Hey, do you want to do something low-key for Valentine’s Day?” text without it being too pressure-y.

The beauty of framing it casually is that it gives him room to respond in kind — and his response will tell you a lot. Does he jump at the idea? Suggest somewhere nice? Or does he suddenly get very busy that week? All useful data points about where his head is. (It’s also useful to have a few ideas/restaurants in mind in advance to suggest yourself.)

If the thought of sending that text makes you want to throw your phone into Lake Michigan, then that apprehension is worth examining too. Are you scared of seeming too keen, or are you genuinely unsure you want to take things to the next level? Sometimes Valentine’s Day anxiety is actually just relationship anxiety in a red bow.

My honest advice: Keep it simple, keep it light and bring it up soon. Six dates in, you’ve earned the right to an overpriced dinner on Feb. 14 without it meaning you’re picking out monogrammed towels together.

If you’re super into the holiday and he’s not, then treat yourself to a nice dinner and/or go out with friends for a Galentine’s Day situation. You’ve got options. And all of them should involve a Ferrero Rocher pyramid.

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