Your first holidays single again, and whether to date through them

The first holiday season after a divorce, a breakup or a death has a way of sneaking up on you. One day it's October. The next, there's a work party invitation for "you and a guest," a group chat planning Thanksgiving (it falls on November 26 this year), and a custody calendar with Christmas Eve circled in a color you didn't choose.

If you're dreading it, you have a lot of company. In the American Psychiatric Association's Healthy Minds Poll last November, 41% of US adults expected more holiday stress than the year before, up from 28% in 2024 (American Psychiatric Association). The top worry, named by 48%, was missing someone or grief, with challenging family dynamics at 32% and loneliness at 31% (American Psychiatric Association). Those may be the three things on your mind right now, and a huge number of people are carrying at least one of them.

So here's the short answer. You'll get through this season best with a plan made in advance, a couple of ready-made lines, and permission to do things differently this year. Dating through the holidays is fine if you want company and would enjoy it. It's riskier if what you mostly want is to stop feeling the date on the calendar. Below is a plan you can make this week, and a way to tell which kind of dating you'd be doing.

Decide now where you'll be on the hard days

The hard days are usually easy to predict: Thanksgiving, Christmas Eve or the first night of Hanukkah, New Year's Eve, an anniversary that lands in December, and the day the kids leave for their other parent's house. The worst version of any of those is the one where you wake up with no plan and too much time.

Get your calendar out and mark them now. Next to each one, write where you'll be and who you'll be with. It doesn't have to be grand. "Lunch at my sister's, home by four" is a plan. So is "Movie and takeout with a friend from work."

Then build in an exit. Holiday gatherings run long, and both grief and family tension tend to show up late in the evening. Drive yourself, or know which train you're catching. Tell the host in advance that you might slip out early, so leaving doesn't become a statement.

Keep one tradition, start one new one

You don't have to keep everything the way it was, and you don't have to throw it all out either. Pick one tradition that still feels like yours and keep it: the ornament you always hang first, the pancake breakfast, the walk after dinner.

Then start one new thing that belongs to this chapter only. A volunteering shift. A Christmas morning hike. A Friendsgiving you host yourself. A trip somewhere warm with a friend.

The old tradition gives you some continuity. The new one gives you something to look forward to that the past can't compete with.

Kid-free days need a plan too

If you share custody, there may be a holiday this year when your home goes quiet for the first time. People tend to underestimate how strange that feels. The wrapping paper is still on the floor, the car pulls away, and suddenly it's silent.

Plan those hours as carefully as the busy ones. Book something for the afternoon of the handoff, such as a movie, a long run or an evening at a friend's place. Some parents find it helps to hold their own celebration with the kids on a different day, so the morning you shared matters more than the date it happened on.

The quiet can also be useful. In a survey by Ohio State Wexner Medical Center, 56% of Americans said enough alone time is a critical part of their mental health (Fortune). A whole day of sleeping in, old movies and leftovers is a perfectly good use of a kid-free holiday.

Have a line ready for nosy relatives

Someone will ask, probably with a head tilt. "So how are you really doing?" Or the sequel: "Have you met anyone yet?"

You don't owe anyone the full story over dinner. Have one short line ready, with a change of subject right behind it. You could say:

• "It's been a big year, but I'm doing okay. How's the new job going?"
• "I'm not up for talking about that today, but thanks for asking."
• "Nobody yet, and I'm in no hurry. Can you pass the potatoes?"

If you expect to be cornered, ask one trusted person at the table to steer the conversation elsewhere when they see it coming. Most people are glad to be given a job.

If you've lost a partner

For widowed readers, the first holidays can be one of the hardest stretches of the first year. Their stocking, their chair, the dish only they ever made.

Some people find it helps to make room for the person on purpose instead of working around the gap. Light a candle at dinner, cook their recipe, or ask everyone at the table to share one memory. Others need to do everything differently this year, somewhere new, with different food and different faces. Both are fine, and you can decide day by day.

You don't need to be cheerful for anyone else's sake. If family is hoping for a normal Christmas and you can't give them one, you could say: "I'd like to be there for part of the day. I'll probably need some quiet time too." That's a complete answer.

A grief counselor or a support group for widowed people can make this season lighter, and it's fine to look for one now, before the hard days arrive. If at any point you feel you might not be safe, or you simply need someone to talk to, you can call or text 988 to reach the 988 Suicide and Crisis Lifeline, which is free to use (988 Lifeline).

When you're ready for the bigger question of whether, and when, to date again, our guide to dating after losing your spouse is a gentle place to start.

Should you date over the holidays?

Some people want nothing to do with romance this season. Others find themselves suddenly, surprisingly interested. Both are normal, and the season has its own pull: in a survey by the dating app Bumble, 48% of respondents said the holidays are the ideal time to meet a partner (Audacy).

December dating can be lovely. The streets are lit up, there are markets and parties to go to, and conversation has plenty to start from. It tends to go well when you'd enjoy the date even if it led nowhere, when your days already have people and plans in them, and when you're curious about the person in front of you rather than just glad of the company.

It goes wrong more often in a few situations. Be careful if:

• You're swiping hardest late at night on a holiday, when you feel lowest.
• A December date not texting back would flatten you.
• Part of you wants someone to bring to the family party so the questions stop.
• You're hoping a new person will make the season feel the way it used to.

Here's a quick test. Would you still want this date in the second week of January? If yes, go and have a nice time. If the answer is "probably not," that's the calendar talking, and it can wait.

Keep the new person away from the family table, for now

If you do meet someone you like, keep it between the two of you for a while. Bringing a new date to a family holiday is a lot of pressure a few weeks in: relatives, children, former in-laws, memories in every room. It's also the setting most likely to make you compare.

A drink on December 27, just the two of you, will tell you far more. If you have children, our guide to introducing a new partner to your kids covers when and how that meeting should happen, and the holidays are rarely the moment.

Your plan for this week

Take fifteen minutes before November gets busy and do three things:

1. Mark the hard days on your calendar and write one plan next to each.
2. Choose your one old tradition and your one new one.
3. Text one friend: "The holidays are going to be strange this year. Can we put something on the calendar?"

Then decide, with no pressure at all, whether dating belongs to this season or to the new year. Either answer is a good one.