We’ve Only Been Dating for 3 Months – Now It’s Valentine’s Day, What Should I Do?

We’ve Only Been Dating for 3 Months – Now It’s Valentine’s Day, What Should I Do?
Stressing out about Valentine's Day? We've got you covered.
Valentine's Day ideas

Have a big question or situation you’re wrestling with? Send us your question in the form at the bottom of this piece.

Q: I’ve been dating this girl for three months and Valentine’s is coming up. I’m not clear on what to do. Isn’t over-doing it as bad as under-doing it at this stage? – David

David doesn’t give us much to work with. Questions abound: how serious/far along is the relationship? How invested is David? How invested is she? When it comes to holidays and gestures is he/she more traditional or not? How good is their communication (and does it feel appropriate to talk about it or not)? Do they live in a major city or a more rural area, where dating traditions can vary quite a bit?

But the key point is clear: in the beginning of a relationship, holidays can be treacherous. Why? Signaling.

Under-do it and you’re saying, “I’m just not that into you,” or worse, “I’m a lazy scrub.”

Over-do it and it can be a red flag: “Oh man I’m so into you please please please love me back?!?”

When it comes to signaling in relationships no holiday is more treacherous than Valentine’s Day; it’s literally about love.

As dating and relationship coach Jonathan Bennett points out, “Valentine’s Day is still very important in current dating culture. Even though it’s pretty much a Hallmark holiday (e.g., the Catholic church took the day off its liturgical calendar), many men and women feel great pressure to have a date or be in a relationship on February 14th.”

That pressure can be especially intense if you’re dating or in a new relationship and don’t feel super comfortable or secure yet. Sound familiar, David?

In David’s case let’s assume the following:

  • The relationship is new, not yet super serious, and boundaries/expectations/titles haven’t been negotiated
  • David is moderately-to-highly invested, or he wouldn’t be worried about the inappropriate signaling of under or over-doing it

Instead of trying to find some mythical Goldilocks gesture (not too big but not too small), we’ve enlisted the help of relationship experts to help you side-step the issue altogether.  The question you should be asking instead is, “What do I want out of Valentine’s day?”

It could be an opportunity to take your relationship to the next level by demonstrating your communication, attentiveness, and creativity.

Or it could be your chance to pump the brakes and inject some independence into a connection you’re not that invested in.

valentines day gift expectations

The advice you need is really dependent upon what you want from a new relationship, and so that’s how we’re breaking it down:

If You’re Unsure/Not That Invested

Who hasn’t been here? Valentine’s day rolls around and you’re seeing someone.

Not alone on Valentine’s: check.

But the thing is, you’re not that into them yet. Or ever. Maybe it’s too soon to tell. Or it’s just a casual thing.

I’ve been in exactly this situation on Valentine’s day and it sucks because February 14 is a pressure-cooker of expectations. So how do you navigate it?

1. Invest Proportionally To Your Feelings

First, don’t assume you have to go big or go traditional (Italian restaurant, wine, roses: wallet-buster). If you’re not invested, it means you’re acting from a place of anxiety,  defensiveness, or over-compensation.

Just because there’s an expectation, be it social, personal, or imagined, doesn’t mean you have to abide by it.

Second, what you do or don’t do says a lot about where you’re at. And it’s OK to be honest.

What does all this boil down to? Invest proportionally to your feelings. Not too much higher, not too much lower. Practice the Middle Way of Valentine’s Day.

“The best course of action is to look at the investment you’ve both made in the relationship and apply that to your Valentine’s Day gift choices,” says relationship coach Jonathan. “So if you two are madly in love and fully committed, even after three months, you should spend a little more and get a more personal gift. But, if you’re more casual and haven’t made much of a commitment (if any), then go for something less extravagant and less personal.”

For the lightly invested, this could include organizing a group outing, invite her, and pay for her drinks. Or picking out a funny, cute gift that signals, “Hey, I’m aware it’s Valentine’s and I like you but I’m not applying any pressure because I like how this is developing at its own pace.”

2. You’ve Got Plans Already

Side-step Valentine’s altogether by making plans with your buds. It’s easily explained by the fact that your plan for an all-dudes anti-Valentine’s outing was planned a while ago, before your budding romance was on the radar.

It definitely sends a… message, but hey – you’re not invested, remember?

3. Communicate Like An Adult

Part of being a grown-up human is practicing honesty in exactly this sort of tricky situation. Choose a moment when you’re both sober, relaxed, and not having sex and open a dialogue about their expectations and yours.

Keep it simple and own the weirdness: “Hey, I know we just started seeing one another and I’m not trying to apply any pressure or bail on you but… Valentine’s Day is coming up and I feel like dating can get weird this time of year.”

Holidays are often catalysts for relationship transitions, and communicating openly about Valentine’s day might precipitate the end of something. That’s OK. If that happens it was coming anyway, sooner or later.

Even if the outcome is painful, you have the satisfaction of knowing you handled things with open, mature communication. Which brings us back to David’s situation…

If You’re Invested

1. Communicate Like An Adult

If the sparks are flying, it may be difficult to choose a moment when you’re both sober, relaxed, and not having sex to open a dialogue. Do your best.

In today’s dating landscape, communication seems to have gotten a bad rap. This is especially true on holidays, when it can feel like the first indicator of a guy’s thoughtfulness is how well he reads his date’s mind.

Forget all that.

Sure, it feels like you should just know what to do for Valentine’s Day. Yes, the relationship is new and talking is weird. Maybe you haven’t had a single serious “talk” yet. So keep it that way.

As marriage and family therapist Dr. Racine R. Henry suggests, “Instead of asking ‘What do you want to do for Valentine’s Day?’ you can ask ‘What would be your perfect Valentine’s Day?’” Keep it playful and use it as an opportunity to learn more about the other person. How do they answer the question? Do they have strong ideas on deck, signaling they want you to be more of an executor that follows orders? Or are they more passive, signaling they want you to show leadership and suggest something?

If you can be attentive and read their signals at this high-pressure junction in your relationship, no matter what the specifics of your Valentine’s day are you’re going to come out ahead.

And if she demurs and stammers something about seeing her girlfriends, that’s important information too. Be cool and don’t jump to conclusions (“She’s not into me!” “There’s someone else… and I’m not cool with that.”) She may simply be trying to take the pressure off, too.

2. Invest Proportionally To Where You’re At

In war, as in dating, there are tactics and strategy. Tactics are the means deployed to gain an objective. They’re immediate, dynamic, in the moment.

Strategy is planning, positioning, and decision-making that shape what tactics are used and when.

While it might seem like a bold tactic to try and level up your relationship by splashing for a blowout Valentine’s day, it’s not a sound strategy.

valentine's day in new relationship


Unless you’re absolutely certain the relationship is ready for it, a shock and awe date on Valentine’s day is likely to backfire because there’s already considerable pressure on both sides to present a Goldilocks gesture – not too eager/intense, not too casual. If one side blows this up, the consequences can be grave.

For example, a good female friend of mine had been seeing a guy for a few months. He said he wanted to take her out for Valentine’s, acknowledging it was corny but that he wanted to anyway. She was charmed.

So what does he do? Take her to five-star haute cuisine mecca Bouley, in Manhattan. As I understand it, Bouley is one of those thirteen course, wine paired, $1000 per head kind of places. In 2015 it was TripAdvisor’s best restaurant in America.

She came away saying, “It was an amazing meal, but it was too much pressure. I can’t believe he did that.”

The sound strategic path to leveling up your relationship is to side-step the Valentine’s pressure-cooker entirely. And you can accomplish that quite simply.

bad valentines day ideas

3. Focus On Experiences

If you’re going to make an effort on Valentine’s day, ditch the chocolate, roses, and five-star restaurants and consider this advice from Certified Relationship Coach and owner of Maze of Love Chris Armstrong:

“The appropriate gesture for today's dating pool, especially millennials, is more about an experience than something you can hold in your hand. In this, it is much easier to plan something without overdoing it. In years and generations past, buying a piece of jewelry or a box of chocolates, for instance, could be seen as over- (jewelry) or under- (chocolate) doing it.

Today, it's easy to make dinner at someone's house or go to a local show. It's hard to overdo dinner or a show because it is about two people spending time together as opposed to one person getting an over- or under- expensive gift from someone.”

That is just such damn good advice.

The pith of what Chris is saying is that when a gesture is more about the thought and effort you put in, rather than the dollar amount you plop down, it’s far more insulated against coming off as too much or too little. Take the capitalism out of it, he seems to be saying; simple, unaffected, and thoughtful are the way to go.

The experience you choose can range from very simple (cooking together with fresh, high-quality ingredients) to sporty (bike ride + picnic lunch) to heartfelt (volunteering at a food bank or animal shelter) to splurge-y (find a Groupon for race car lessons or take a hot air balloon ride). Whatever the case, when Valentine’s becomes an excuse to do something novel and fun it’s no longer about the appropriateness of the gesture, but simply having a memorable, top-tier date night.

If The Relationship Is Good, You Can’t F Up

In closing, I offer David this sage advice (and possible bromide): If this person really likes you, you kinda can’t screw it up. As long as you put in a good effort, they want you to succeed.

Focus on experiences and keep it fun. You’ve hit a home run if, in the middle of the date, you’ve totally forgotten it’s Valentine’s day at all.

Read the rest of the Gentlemanly Advice series.

Stillman Brown

Stillman Brown is a writer and TV producer who has created prime time content for National Geographic, Discovery, Travel Channel and many others. His interests span science & the natural world, personal growth, and food. He lives in Tulsa, Oklahoma.