The New Rules of Cuffing Season
Illustration: Olivia Fields

The New Rules of Cuffing Season

Are you looking to lock someone down if we go through another lockdown?

October has arrived. Know what that means? Yes, it’s fall. Know what else? Sure, election season — get on that. But there’s another phenomenon folks seem to get all antsy about around this time of year. That’s right. It’s cuffing season!

For the uninitiated, cuffing season is that ever-thirsty time of year in which happily single folks start looking ahead to cooler temperatures, holiday dinners, and, depending on where you live, snowstorm snuggling. This time of year ushers in seasonal situationships that climax right around Valentine’s Day, when cuffers decide whether they want to return to singlehood for the spring and summer.

You can take all the care in the world, yet if lines become blurred, cuffing season can turn into a shitshow.

There’s a negative connotation that cuffing season carries because, technically, no one should go into a relationship for just a season — particularly if the other person isn’t on the same page.

These post-Covid-19 times pose some interesting challenges for the cuffing season, but I’m all for fellow singles coming together (hopefully) and deciding to pair up throughout the cold months. If it’s you, dear reader, here are some considerations you might want to bear in mind.

1. You might end up like Jerry and Elaine from Seinfeld

In a now-classic Seinfeld episode (immortalized by Wale and SZA), Jerry and Elaine, who had previously dated, decide to become friends with benefits. They go through this whole process of outlining the rules (spending the night is optional!) and try to move their friendship (this!) into the bedroom (there!) without ruining anything. It’s ruined, of course, when Elaine’s birthday rolls around and Jerry gifts her cash with a shrug — and she no longer wants the benefits or even the friendship. The moral: You can take all the care in the world, yet if lines become blurred, cuffing season can turn into a shitshow.

2. Be honest (no, really)

So, you’ve met someone with whom you wanna cuddle throughout the cold months, and you’re both on board for a good time, not a long time. Great. Have your fun. But can you really be sure no one catches feelings as you go on cute dates during the holiday season? Communication is important — make sure there are semi-regular talks where you each explain and/or reiterate where you stand. Just because you both agree to the arrangement in October doesn’t mean those feelings won’t change come March. No one should feel blindsided when the fling flames out.

3. Consider abstinence

A surefire way to keep everyone on the same page throughout cuffing season is to keep things platonic. Hey, maybe you’re really just looking for a plus-one to go ice skating with. If things naturally grow more intimate, you might just realize there’s something there worth exploring beyond the winter months.

4. Annuals vs. perennials

Mother Nature has all of the answers. For this lesson, look no further than horticulture. There are annuals, which die off after one season, and there are perennials, which die off but then return the following year. Guess which are planted in fall, parallel with the start of cuffing season? Yup. Perennials. I’m not saying every cuffin’ buddy turns into a Same Time, Next Year situation, but you’ll figure out what works for you.

5. The more, the merrier

Many of us have created safe pods in our post-Covid-19 world — that core group of friends and family members with whom we’re comfortable in-person social distancing. Instead of locking down one person, how about creating a community of people who will hold you down during this first post-Covid-19 holiday season and beyond? Host your own gatherings. Skip the high-pressure family functions. If the event makes you feel like you need to have a partner in order to feel comfortable, maybe you don’t need to be there.

6. Date with intention

Wanna know the truth? Cuffing season is a myth. Do people tend to pair up more as the weather cools? Sure. But do they do so even if they’d rather be single and they’re ready to make a break for it as soon as the temps increase? I don’t think so. Here’s the real deal: We often find ourselves in relationships that don’t fit because we made choices based on this imaginary season. And that is why these relationships don’t last beyond Valentine’s Day. It’s not people ripping off the cuffs and hightailing it into summer. So how about this fall, you think about what you want in a partner, make a nonnegotiable list, decide to be your best self this season, and see who shows up? You never know; your next Memorial Day date might be a winner.