Singles across America, and especially in the Upper Midwest, now is the time for Cuffing Season. I’ll do my best to guide you in navigating this unique time of the year, plus with COVID-19, it feels a little different this time around.

What is Cuffing Season?

For the uninitiated, Cuffing Season begins when the weather gets that chill in the air, the nights get a little longer, and the clothes go from shorts to sweat pants.

In Chicago, Cuffing Season can begin as early as right after Labor Day. This year we had an incredible summer with extended nice temperatures. So, for me, I would say this week marks the official opening of Cuffing Season – the temps in the 50s and low 60s seem to have hit.

So, you ask, what the hell is Cuffing? My married friend laugh at the idea, but the chronically single have a pattern when it comes to the season. See my Seasons of Dating article below:

When the weather gets colder, it is only natural to want to snuggle up with someone to keep warm. The Cuffing part is just locking in on one snuggler over another for the duration of the Hibernation Days of Autumn and Winter. I mean it makes sense right, when the weather is awful out, who wants to get out and prospect for someone new when you have that warm body next to you right now. A Cuff in the Hand is worth 10 Trips to the Bar.

Biology or Psychology

Cuffing Season, in my humble opinion, is equal parts Biology and Psychology. I do think that biologically we as social creatures want to bond with someone during the winter. Generations of surviving winter means protecting one another, keeping each other warm, and of course procreating. Look at my family. My Irish side has like 4 of the 8 aunts and uncles born in August or September. That means fall/winter conception. What else are you gonna do when its cold outside, right?

On the psychological side, with the holidays coming, most people do not want to be alone. It feels better for some people to have someone with them at holiday parties or to do all those festive activities together. We feel more alone sometimes if we aren’t sharing those experiences with someone else.

How to Approach Cuffing Season

Cuffing Done Right
  1. Know that Cuffing Season is a Thing – Some people may think this is all bullshit, but being single on and off over a couple decades, plus other experience shared with my friends, believe me it exists. It’s always more helpful to know that the general trend exists.
  2. Figure Out if Cuffing Is for You – This gets back to some of my older dating tips. You have to know what you want. One should not jump into Cuffing Season lightly. Cuffing by its very nature means a longer term connection than a one night stand. Certainly Cuffing can turn into a real, fulfilling relationship. However, Cuffing can also be a matter of convenience, too. So, if you are prone to getting crushed after a Pre-Valentine’s or early spring break up, then weigh the risk/reward of going full Cuffing.
  3. Pick Someone You Can Spend Deep Time With – Cuffing is more than just sex and snuggling in bed. Typically, you are going to be doing a lot of quiet nights at home – the classic Netflix and Chill routine. So, not everyone is cut out for that type of duty. Great sex (always my preference) may not come from the same person who can chill and watch a movie with you. Just keep that in mind when making your selection.
  4. Set Expectations Early – I suppose this entire article is just a refresher in dating, but it is important to be clear with your potential Cuff what you want out of all this. Maybe you can just find someone who is a Snuggle With Benefits person. They want to sit in sweatpants, stream some shows with you and maybe some good sex for a few months. Or maybe this Cuff is more into a longer term relationship. Either way, be clear on what YOU WANT, and everyone will be better off. Just falling into something is ok, but no one wants to get their heartbroken.

COVID Caveat

A lot of you singles out there may have done a precursor to Cuffing Season in the early quarantine. The term then was called COVID Bae or the person you got through quarantine with. So, many of you may already have your cuff or know the basics on what to figure out when selecting an appropriate Cuff for the season.

I, personally, think that this Cuffing Season, unlike most years, may result in even more longer term partnerships. COVID has brought us together and “surviving” stressful times can create a lasting bond beyond quarantine or even a good Chicago winter.

Full disclosure, I am the not a great Cuffer. So, I’ll likely sit another Cuffing Season out. Sure, I’m going to date. I will tread lightly in getting completely Cuffed. My problem is I tend to Cuff ignoring every red flag in the book, and next thing you know, I’m married again.

Look, we all have biological and psychological needs. It’s important to meet them in the healthiest way possible. Cuffing is definitely going to happen, in spite of COVID. Expect dating activity and connections to increase a lot more over the next couple months. Just know what you want and I hope you find it. I would love to hear your Cuffing Stories, if you are willing to share.

Wegs