5 Tips On How To Survive Cuffing Season — And Turn Your Winter Fling Into A Long-Term Relationship

Photo: Daniel Silva Gaxiola on Unsplash
How To Survive Cuffing Season — And Turn Your Winter Fling Into A Long-Term Relationship

So here we are again… Every year during the transition into the fall season, you start to notice a major shift in the dating scene.  People start approaching you more for dates, you start getting “Hey Stranger” messages from old flings and you find that men seem a little more open to the idea of the exclusivity of dating than they were during the spring and summer months.  Ladies and gentlemen, it is officially “Cuffing Season.”

You may or may not be familiar with the cuffing cycle so let me break it down for you:

(Hand) Cuffing Season usually runs from Labor day and continues through Halloween. This is the period where most singles, mostly men, come to the realization that they do not want to be alone during the holiday season .They realize that they would like to have a cuddle buddy to either:

A) Keep them warm as the weather gets colder.
B) A trophy to show off at family, career or friendly gatherings. This is how we avoid the uncomfortable “when are you going to settle down?” conversations with their peers.

As a result, they become a little more concentrated on finding someone to play this part in their lives and they put in some major effort to ensure they get it.

Upon first glance, it doesn’t seem like a bad option, and in reality it’s not. We all have needs and the idea of finding that ideal cuff can be viable solution.

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I do have to warn you though, these relationships typically have a 5-7 month shelf life.

As soon as Spring comes around, singles start to think about the summer. Vacations, parties, plans with buddies start to come into play and various ideas of all the fun to be had takes priority over being in a relationship. Then comes the famous prelude to the conversation we all hate “We need to talk.”

Not all relationships birthed from cuffing season fail. There is potential for this extended booty call to become something long-term, if you play your cards right.

Here are my top tips on surviving cuffing season and making it work for you.

1. Get Your Mind Right

Anytime you date, you always want to have an idea of what it is you want to gain from the experience. You want to have a clear goal in mind so you can conduct yourself accordingly. This opens your mind up to the opportunity and makes it a little easier for you to get what it is you are after. Whether your needs are for casual companionship or long-term exclusivity, you should make sure your mind and your actions compliment your desired outcome.

This means: if you are looking for something casual, be upfront about it and don’t lead the person on. Or if you are looking for something long-term, don’t entertain a sex buddy (or buddies).

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2. Choose Wisely

During cuffing season you are going to have a few prospects make their interests known. Of course there will be some new acquaintances, but there will also be a slew of old flings vying for your attention. Whatever your options, make sure you weigh the pros and cons of a potential partnership.

Make sure you are compatible with your choice. The worst thing you can do is cuff with someone you can only tolerate in small doses. You will just end up causing yourself a lot unnecessary stress and I am certain that you have better things to worry about.

This is especially true with guys who send you the random “hey stranger” messages. Take a moment to think about why things didn’t really work out the 1st or 2nd time around before you give them a chance. Chances are that whatever it was that caused you not to vibe with that person has not changed and you might be better off investing that energy into someone else.

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3. Don’t Move Too Fast

All things take time and this is especially true when you are connecting or reconnecting with someone. Try not to get caught up in the whirlwind by moving too quickly. Take your time to figure the person out and what makes them tick. Don’t come on too strong and let things develop naturally. If your partner is on the same page, the connection between you will be easy to foster.

RELATED: How To Know If You're Falling In Love — Or If Cuffing Season Has You Fooled

4. Treat It Like A Real Relationship

So once you have settled on your boo for the season, do not sleep on opportunities to woo them. Just because you two have come together during cuffing season doesn’t mean that the relationship deserves mediocre effort. Capitalize off these opportunities to impress them with your natural charm.

This means that you dress up every now and then and also, go on dates outside of the house. Ordering in and watching Netflix can be fun, but don’t make it a routine. Keep the relationship active and fun so the both of you don’t get bored with each other.

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5. Don’t Be Afraid To Un-Cuff If Needed

If the relationship isn’t working out, don’t be afraid to let it go. Don’t create any extra stress in your world for the sake of holding on to something that doesn’t work for you and that goes for anything in your life that not serving a positive purpose. Just let the person know how you feel and make a clean break so you can move on.

RELATED: If These 6 Things Are Happening Around You, You'll Know It's Cuffing Season

Besides being a YourTango Dating Expert, J. Cameron Gantt is the Head Dating Coach at Insti(Gay)tor, a Chicago-based GLBT matchmaking agency. Download his FREE E-Guide 3 Secrets To Attract More Dates or contact him directly for a FREE 60 minute consultation.