Nov 3, 2017 Relationships

Beyond Cuffing Season: 5 Fall Dating Tips Straight From an Expert

by Gabrielle Savoie

Christian Vierig/Getty Images

As Aziz Ansari pointed out in his book Modern Romance, the modern age of dating is a perilous and confusing place. In an era where feelings are best expressed with emojis and the word "commitment" is scarier than "indictment," first dates—and their ensuing courtship—can feel more like walking through a minefield: Make it through to the end unscathed (and possibly in a serious relationship), or take one wrong step and have your heart blown up into pieces.

As if this wasn't enough, the colder months add one additional layer of confusion: cuffing season—or the temporary coupling of singles who would rather endure a short-lived "relationship" than brave the cold to find new potential dates. Cuddling sessions in the colder months don't sound so bad, except for one hiccup: When winter ends, so does cuffing season, along with the relationship you may have been building for months. While this might sound scary enough to declare celibacy all winter, it doesn't have to be. We reached out to Nikki Lewis and Greta Tufvesson, co-founders of The Bevy, a personal matchmaking service, to get their take on dating during cuffing season. Ready to take the leap into the confusing world of modern courtship? Brush up on these fall dating tips before stepping out on your first date.

Jumping back into dating can be scary—especially in the thick of cuffing season—but the first step is to figure out what you want to get out of it. "Sometimes you might be the one only looking for cuffing because it's convenient for you," remarks Lewis. "Are you ready? Are you over your ex? If you're not over them, are you serious about putting it in the past and moving toward something more sustainable? Are you willing to make the sacrifices necessary to make a long-term relationship work? Are you happy with yourself both mentally and physically to allow someone else in?" These are just a few questions to ask yourself before jumping back into the dating world.

Tufvesson believes in the power of honesty when it comes to dating. "Always address your intentions head on—ideally during the first date. But also ask yourself if you're being true to yourself," says the matchmaker. "You may have been burned in the past and are scared to open yourself up again. But maybe it's worth giving them a shot."

If you aren't feeling it, she recommends being honest right away. "We're about being real and direct," she says. Instead of going the classic ghosting or slow-fade route, she recommends sending a brief text that clearly indicates you've had a great time but that you aren't interested in getting romantically involved. In other words, honesty is always the best policy.

If you are serious about finding a lasting relationship, The Bevy co-founders recommend looking out for signs that your date might not be on the same page. "Make sure you're selecting someone who is serious about a long-term relationship," warns Tufvesson. "Many players find themselves cuffing simply because motivating to go out in the cold is hard. They will end that relationship as soon as the sun comes back out. Pick your date's brain, and take extra care to notice the warning signs." Here are some signs you can take note of if you're unsure about your date's intentions:

  • They broke up with their ex last week and have no good reason for it.
  • They ask you out at the last minute, including the day or night of.
  • They aren't discussing future plans—holiday travel or the following year.
  • They talk wistfully about how their friends are out on the town.
  • They talk about awesome future plans but don't include you in them.

It may be tricky to open up to someone you've only recently started dating, but just as you should be open and upfront on the first date, it's important to trust your intuition as to when you should have "the talk." "Feel it out, and don't stress about it," advises Lewis. "Some people define the relationship after a week, after a few months, and some after a year. There aren't rules, per se, but if it's bugging you and you want to lock it down, it's a good idea to be honest and direct. If you're seeing someone a few times a week and are in constant contact, it's fair to ask after three to five months. Constantly remind yourself that you have nothing to lose. By opening up to someone and being vulnerable, direct, and true to yourself, you're being real and your best self. If your date isn't into that, it's a good thing that you dodged a bullet."

"Cuffing season is a good platform to start a relationship if that's what you're really looking for," says Tufvesson. "But you have to really give someone a chance. Maybe it's someone who surprises you or someone who you might not have originally been drawn to. The best way to find out is to see it through."

She also recommends switching up your first date ideas from the classic drinks and dinner to get to know your date in multiple environments from day trips to see the fall foliage to weekend getaways with friends.

Next up: This common mistake can jeopardize a first date.