Sugar Dating During the Holidays: Cuffing Season, Holiday Trips and the Scams That Come With Them

Every year, somewhere around the first cold weekend of October, people start looking for someone to spend the winter with. By the first Sunday in January, dating apps have their busiest day of the year. Hinge says that day brought a 31.2% jump in likes and a 24.5% jump in messages over an ordinary Sunday, per Global Dating Insights' January 2026 report.

Sugar dating rides the same wave, with a few twists of its own. Holiday schedules open up, people travel, and the idea of flying someone out for a long weekend suddenly has a natural excuse attached. So does the oldest scam in the book.

This guide is for both sides: men planning a trip, and women deciding whether to take one.

Why sugar dating gets busier in cuffing season

"Cuffing season" is the half-joking name for the months when single people stop wanting to be single. Nights get longer, the calendar fills with parties where everyone else brings a date, and a family dinner full of "so, are you seeing anyone?" questions gets closer. None of that is scientific. All of it is familiar.

There are practical reasons too. A lot of people have time off between late December and early January, which is rare for anyone with a demanding job. Work travel slows down, so the man who spends October in airports finally has a free weekend. And the start of a new year makes people want to change something, which is part of why early January is the busiest stretch of the year for dating apps.

For you, that means two things. More people are looking, so it is a good time to be on a platform. And more people are looking for the wrong reasons, so it is a good time to be careful.

Planning a holiday trip together

Arranged is built for people who travel. Distance is a tiebreaker in how we show matches, not a cutoff, because the person worth meeting is often a flight away. The holidays are when that flight is easiest to justify and hardest to book, so plan for both.

Book earlier than feels romantic

Holiday fares climb and hotels in popular cities fill up weeks ahead. If you are a man thinking about flying someone out for a December weekend, start the conversation in early November, not on December 18th. A last-minute invitation also lands badly: it reads as "my plans fell through" rather than "I wanted to see you."

Meet first, travel second

A holiday trip should not be your first meeting if you can help it. A coffee or a short dinner beforehand, even a video call if you live far apart, tells you both whether a long weekend is a good idea. Our guide to dating someone in another city covers how to tell early whether the distance is worth it.

If the first meeting does have to happen on a trip, keep it small. One or two nights, not a week over Christmas.

The rules that don't change because it's December

• Flights are booked by the man inviting, in her name, and she gets the confirmation directly from the airline.
• She has her own room, offered before she has to ask.
• She has a way home that does not depend on the trip going well.
• Someone she trusts knows where she is going and when she is due back.

These are the same rules as any other month. The difference is that holiday trips feel more meaningful, so people are tempted to skip them. Don't. Flying her out: a man's guide to the first trip goes through each one in detail.

Pick a city that isn't shut

Plenty of restaurants close on Christmas Eve and Christmas Day, and some cities go quiet for most of the week. Check before you book. The days just before Christmas and the stretch between Christmas and New Year's are usually easier than the holidays themselves, and they are better for a first trip anyway, because nobody feels like they are missing family plans.

For what to actually do once you land, see first date ideas when you travel. A holiday market, a winter light display or an afternoon at a museum beats the hotel bar every time.

New Year's Eve plans with someone new

New Year's Eve carries more weight than any other night of the year, which is exactly why it is a risky choice for an early date. The expectations are high, everything is overbooked and overpriced, and midnight comes with a script that two people who met last week may not be ready for.

If you have been seeing each other for a while, a New Year's trip can be wonderful. If you haven't, try this instead:

• Plan a dinner on the 30th, or a long brunch on New Year's Day. Same celebration, a fraction of the pressure.
• If you do go out on the 31st, pick a place with a reservation and a set end time, not a party you can't leave.
• Agree how each of you is getting home before the night starts. Rideshare prices and wait times are at their worst after midnight.
• Say plainly that a midnight kiss is not part of the deal unless you both want it. It takes one sentence and removes the awkwardness entirely.

Look, the best New Year's Eve with someone new is one that leaves you both wanting a second date in January. Aim for that.

Meeting safely over the holidays

The basic safety rules for a first date don't change in winter, but the holidays add a few wrinkles. Our first date safety tips cover the fundamentals; here is what changes in December.

It gets dark early. A "daytime" first date at 4pm in New York in December finishes in the dark. Pick somewhere central and well lit, and plan the trip home before you go.

Holiday parties add alcohol. If the first meeting is at a party or after one, you are making decisions with less information than usual. Meet sober first, or at least meet before the party, not after it.

People are busy, and that hides things. A match who "can't video call because of family stuff" for three weeks in December might be telling the truth. They might also be someone who will never video call. Ask once, plainly, before any trip is booked. Someone real will find ten minutes.

Your friends are busy too. Tell someone where you are going and when you will check in anyway, even if they are at their own family dinner. A two-line text costs them nothing.

Holiday-season scams: flight money, gift cards and the Christmas sob story

Romance scammers love the holidays for the same reason honest people do: there is a built-in reason for everything. A flight home. A gift for a sick relative. Rent that is due right when nobody has spare cash. The excuse fits the season, so it doesn't sound like an excuse.

The numbers back up how common this is. In the FTC's February 2023 Data Spotlight on romance scams, gift cards were the most frequently reported way people lost money to romance scammers in 2022, named by 24% of people who reported a loss. The most common lie the FTC found was "I or someone close to me is sick, hurt, or in jail."

The "flight money" ask, both directions

Aimed at women, it looks like a man who offers to fly you out for Christmas, then asks you to book the ticket yourself and get reimbursed, or "accidentally" sends too much and needs the difference back. Aimed at men, it looks like a woman who would love to come see you for New Year's but needs the airfare sent first.

The answer is the same either way. A man who is flying someone out books the ticket himself, in her name. Money never moves through the person traveling. Our breakdown of the flight money scam covers every shape it takes.

Gift card requests

"Could you grab me an Apple gift card for my little brother? My card isn't working." Any request for a gift card from someone you met online is a scam. There is no holiday exception. Gift cards are asked for because they can't be traced or reversed, and the FTC's own data says they are the scammers' favorite.

The sad-story ask

Her mother is in hospital and she can't afford to fly home for Christmas. His account is frozen over the holidays and the bank won't open until January. Her heating was cut off. The details change, the timing doesn't: the emergency arrives after a few days of warm conversation and before anyone has met.

Real people have real emergencies, including in December. But a stranger whose emergency can only be solved by your money, right now, is not a stranger you should help. If you are a man being asked for money before a first meeting, read what a sugar baby asking for money before meeting usually is. The reply that works for both sides:

"I don't send money to anyone before we've met, but I'd really like to meet. When are you free?"

Someone interested will pick a date. A scammer will push, invent a deadline, or vanish.

What Arranged does about it

On Arranged, phone numbers, WhatsApp, Telegram and other contact details can't be sent in a conversation until the other person has replied, which stops the "let's move this off the app" step most of these scams depend on. Copy-paste messages sent to lots of people are blocked, and accounts that keep trying either trick are suspended automatically. Email verification is required before anyone can message.

Photo verification is optional and reviewed by a person; verified profiles show a badge. We do not verify income, and not every profile is verified, so the badge is a good sign rather than a guarantee. A video call before a trip is still on you.

Gifts without the weirdness

The holidays come with gifts, and that is fine. The best ones are thoughtful rather than expensive: a book she mentioned, a dinner somewhere he has wanted to try, tickets to something you can do together, a nice version of something they use every day. Experiences tend to land better than objects early on, because they become a reason to see each other again.

A gift is a gift. It is not a down payment, a test, or a way to keep score, and nobody owes anyone anything for receiving one. If a gift comes with expectations attached, it isn't really a gift. And if someone you have never met is asking for one, see the section above.

What to do this week

If you want someone to spend part of the season with, start now. Late October and November are when the planning happens; by mid-December, the good dates are booked and the flights cost more.

Browsing profiles, liking and matching on Arranged are free for everyone, with full photos. Women message free; men need Premium ($49.99/month) or Diamond ($99.99/month) to send and read messages. We're smaller than Seeking, and distance doesn't hide anyone, so the person worth flying out may already be there.

Frequently asked questions

What is cuffing season in sugar dating?

It is the stretch from roughly late October to February when more people look for someone to date. In sugar dating it lines up with holiday time off and holiday travel, which makes it a natural time to plan a trip together.

Is it a good idea to fly someone out for Christmas?

It can be, if you have already met or at least video called, and the trip is short. Book the flight in her name, offer her own room, and make sure she has a way home that doesn't depend on you.

Should a first date be on New Year's Eve?

Usually not. The night comes with high expectations and logistics that are hard to control. A dinner on the 30th or brunch on New Year's Day gives you the celebration without the pressure.

Someone asked me for flight money to visit over the holidays. Is it a scam?

Almost certainly. Someone genuinely flying you out books the ticket in your name. Someone asking you to send airfare, or to book it and be reimbursed, is running one of the most common holiday scams.

Is it normal to be asked for a gift card around Christmas?

No. A gift card request from someone you met online is a scam every time, holidays included. Gift cards were the most frequently reported payment method in romance scams in the FTC's 2023 data.

Can I use Arranged to meet someone in another city over the holidays?

Yes. Arranged treats distance as a tiebreaker rather than a filter, so people in other cities still show up. The holidays are a natural time to plan that first trip.