How To Navigate Cuffing Season (Including Instant Red Flags)

Thinking about getting cozy with someone this year? Consider reading this first.

Man and woman get cozy during the holidays
Photo design by BrownStyle Magazine

Welcome to cuffing season, a time of year when single folks from different walks of life engage in romantic relationships in hopes of staying warm and cozy during the long winter months. Although cuffing season can be a heartwarming time— offering a wonderful chance to forge new connections and create lasting memories through warm embraces and cozy movie nights— it can also come with its share of challenges.

According to Jes Averhart and Terresa Zimmerman, that’s why it’s essential to pay close attention to the potential red flags that might surface during the seasonal pursuit of companionship. The authors of Oh, Lords!: Who We Date, Why We Date Them, and What We’ve Learned recently sat down with us to help us navigate cuffing season and shed light on the common red flags to watch out for. Keep reading to get their helpful insight.

What Is Cuffing Season?

Woman and man eating breakfast in bed
Photo by Polina Tankilevitch

While there is no exact date on the calendar that tells us when cuffing season begins, it usually begins as the temperatures start to get cooler—particularly during the holiday season.  

“The phenomenon that is ‘Cuffing Season’ usually starts after Halloween and ends just before Valentine’s Day,” Averhart explains, adding there is a strong possibility that these seasonal relationships can last until April. “During this time of the year, single people who were living their best lives outdoors over the Spring and Summer begin to search for someone to snuggle up with as they settle into the cooler and cozier Winter season.” 

How To Know If He’s Interested…

Zimmerman says one of the biggest misconceptions about cuffing season is that women are the only ones who are looking. She says that’s farthest from the truth. 

Averhart co-signs, adding that during this time of the year, it’s highly likely that you’ll notice a spike in DMs from men who you haven’t heard from for years or months. More than likely, they will shower you with flattery to make you feel special. They may also invite you to social events to make you feel as though they are invested in taking your relationship to the next level. 

Know Exactly What You Want

If you are looking for a lasting relationship and some guy hits you up out of the blue in mid-November, it’s probably not the universe or fate at play.

“During cuffing season, you can expect to get a call or DM from men that you haven’t heard from for months or years,” Averhart reminds us. “Stop romanticizing everything and ignoring the little voice that says, ‘Hmmm where’s this coming from?’ and ‘Why now?’”

Interested in pursuing a relationship with this person? The authors say go for it. However, they caution you to know what you want and don’t be afraid to set boundaries. 

Woman reading a book
Photo by Vlada Karpovich

How To Set Healthy Boundaries 

Averhart highly suggests being clear about what you want and saying ‘yes’ or ‘no’ to invitations with confidence. “If that’s what you want, go for it! Just don’t bury the headline. Be honest about it and take the pressure off the table,” she suggests. 

She also reminds us to never be at the mercy of someone else’s wants and needs for 120 days of the year. “You never know, maybe the relationship could blossom into something more, or maybe it’ll fizzle out at the first hint of Spring. Either way, talk about what you want and then have fun. Self-respect is when you move with pride and dignity,” Averhart notes.

Warning: Pay Attention To The Red Flags

According to Averhart, ghosting is a definite red flag during both cuffing season and relationships in general. 

“Men and women who are only looking for the girlfriend/boyfriend experience during cuffing season are going to start ghosting you when the weather starts to warm up or someone else piques their interest,” she shares, adding this will translate to fewer visits, calls, and texts. 

Another sign is being sidelined. If you’re not being introduced to friends along the way or the introduction lacks enthusiasm and connection, you’re likely a fun, but temporary, solution to the Winter blues.   

Woman and man sitting on a bed after a disagreement
Photo by Alex Green

Cuffing Season: Is It A Bad Thing?

Let’s face it, for some singles, it can get lonely on cold dark evenings. The Winter Blues are a real thing, and a great way to counter those feelings is to share time and space with someone. However, a lack of honesty will always prove to be a problem in any form of relationship. 

“The problem with cuffing season is when you use someone out of desperation or loneliness to make YOU feel better,” says Averhart. “Trust me, if you’re not clear about how you’re approaching your relationship at that moment, you’ll be untangling an emotional mess later.”

Averhart warns that if you are going to participate in cuffing season, don’t dive headfirst into a couple-dom. It’s best to take your time and enjoy the moment for what it is. 

Be Honest With Yourself—And Others

If you are looking for a successful cuffing experience, Zimmerman suggests getting out of your way and being intentional. “Ask yourself what you are looking for and what you want. Then open yourself to it and go get it, girl,” she adds.

Over the years, Averhart says she’s learned so much about herself as she navigated cuffing season as a single woman and as a woman exploring a new relationship.

“In both cases, I learned a ton about what I wanted in a healthy relationship and who I wanted to be in the world and for a partner,” she explains, adding this time of year can be vital for personal growth and reflection. “It’s a time to anchor yourself in how beautiful, talented, and amazing you are as a woman with or without a partner. I started my business during the cuffing season of 2019. I was energized, clear and focused. Not having the distraction of a relationship set me up for a successful launch and filled my confidence cup.”

Overall, Zimmerman reminds us that you are not alone in your desire for a relationship, cuffing or not. “We all struggle. It’s within our power to know who is in our life and how they are in our life, or not,” she says. “If you take some time and define what you want and then honestly open yourself up to your choice, you can make it happen successfully.”

Easier said than done, yes. Worth it? Absolutely!

Editor’s Note: This story has been edited and condensed for clarity.