Cuffing Season

With summer behind us, we enter cuffing season. That time of the year where everyone is looking to find someone to hibernate for the winter with. This is the perfect time to become more serious about your dating life. There are many ways to meet people - both online and offline.

If you’re looking to meet someone offline, go to places where you can meet the type of person you’re looking for. The fall is such a great time to meet people with everyone back from the summer and football season gearing up. If you have a favorite sports team, go to the bar where you’ll meet other fans. There really isn’t an easier conversation opener than seeing someone supporting the same team as you. Ask them if that’s where they’re from originally or if they went to school there. You’ll instantly have something to bond over and it will feel authentic. If you’re younger, go to bars that cater to younger people. If you’re older, find more mature sports bars so you can meet your ideal market.

I’m constantly asked about how to turn dating app connections into actual dates. It can feel like endless conversations that lead to nothing. It can feel disheartening to be rejected by someone who hasn’t even met you yet. Firstly, don’t take it personally. You never know what they have going on in their lives that has nothing to do with you. I also recommend bypassing all of the chit chat by sending a direct message. Some of my favorite openers are, “I have a feeling I might be thirsty on Wednesday, want to join?” or “I’m going to want a spicy margarita after work tomorrow, know anyone who might be interested?” something cute but direct. You’ll bypass all of the endless boring conversations and get a date on the books. Even if you match with someone you’re excited about, the ongoing chit chat can make you feel less excited about the connection. Give it a try next time you’re on the apps and see if this method works for you. It’s easy to experiment on the apps because there is no real way to lose. If they don’t respond, just move on and message someone else!

Make the most of this time and put yourself out there. If you’re a little nervous approaching strangers, start by smiling and making eye contact. You’ll see that most people will be receptive to someone who looks happy and engaged. You miss 100% of the shots you don’t take!



Anna Morgenstern