Run Game Conversation

Valentine's Day and holiday dating: what to plan

6 min read

If you've been seeing someone for a few weeks, Valentine's Day has no standard answer. Some people treat it as a big night, some skip it on purpose, and a lot of people haven't decided. A common approach is a short, relaxed conversation about it, ahead of time. The rest of this post covers what surveys say, how to plan around the crowds, gifts, other holidays, and what to do if you're single.

What the numbers say

The National Retail Federation runs a yearly survey with Prosper Insights & Analytics. The 2026 edition (7,791 U.S. adults, January 2 to 8, margin of error plus or minus 1.1 points) found:

That survey covered everyone, not just people early in a relationship, so it tells you what's common overall and not what's expected on week three. Spending is a group average. Plenty of people spend nothing and are happy.

A smaller and older source speaks to early dating more directly, with caveats. A 2017 survey by the matchmaking company It's Just Lunch (over 1,400 respondents, method not described) reported that 38% of men and 26% of women would expect to spend Valentine's Day with someone they'd dated only one to three times. It also found 53% of women saying a gift of $50 or less is appropriate at one to three months, and 22% of women expecting no gift (the page doesn't break that figure out separately). Treat it as one company's poll, nearly a decade old. It does show that people's views differ, including within the same group.

Planning around booked-out restaurants

Valentine's Day is one of the busiest nights for restaurants. A 2019 OpenTable and Toast analysis reported by Restaurant Dive projected reservations to rise 433% compared with non-holiday Thursdays, and bookings for two to jump 764% (against a typical night, so the two figures use different baselines). Those were projections, not measured results, and they're from 2019. The pattern is still familiar: popular places fill early, and the day itself is a hard time to find a table.

In 2027, February 14 falls on a Sunday. A few ways to deal with a crowded calendar:

Gifts and expectations

The honest answer is that it depends on the person and how long you've been dating. A few approaches people use (a rule of thumb, not a standard):

How long you've been seeing each other Low-key options
A few dates A coffee or a walk. Probably no gift. A short message is plenty.
One to two months A small card, a favorite snack or a plant. A casual dinner.
Exclusive or longer Something personal. A planned evening. A conversation about what each of you likes.

Some people think Valentine's Day is overly commercial and would rather skip it. Others like it and look forward to it. Neither view is the expected one. Many people see price as a poor stand-in for feelings, and people read it differently, so a common approach is not to treat what she spends or doesn't spend as a signal.

If you're unsure, ask. Here are a few ways to put it:

Asking early gives her room to say what she wants without a surprise she has to react to. How openly to show you're keen in those first weeks is a separate question, covered in how much interest to show. First date ideas and second date ideas have more low-key plans, and dating on a budget covers keeping costs down without it looking like it.

If you each want something different, that's fine too. One of you wants a quiet night, the other wants a restaurant, so pick one and swap next time, or find a middle option such as a short dinner out and a movie at home. If she tells you plainly she doesn't want to do anything, take that at face value.

Other holidays

Most of the same logic applies to other times of year. A few practical points:

If you're single on the day

About 45% of adults in that NRF survey didn't plan to celebrate, so you're not alone. Some practical ideas for February 14, and for other holidays:

Neither mood is wrong. Some people feel it more on this day, and some forget it exists. Do what makes the day feel normal for you.

What to do next

  1. About three to four weeks before February 14, decide whether you're planning anything, and who you'd plan it with.
  2. If you're seeing someone, bring it up casually: "Do you do anything for Valentine's, or skip it?" Listen to the answer.
  3. Pick one plan that fits where you are. A few dates in, a coffee is enough. Longer, a dinner.
  4. If you want a restaurant, book it early, or choose another night in that week.
  5. Keep any gift small and personal, and don't equate cost with feeling.
  6. For other holidays, ask about plans in the weeks before, not the days before.
  7. If you're single, put one plan with friends on the calendar so the day isn't empty.

Sources