The Shy Person's Guide To Having A Summer Fling

photographed by Caroline Tompkins; produced by Julie Borowsky; produced by Lorenna Gomez-Sanchez; modeled by Shelby Fenton; modeled by Tayler Smith.
The first steps to any summer fling are to have fun and be yourself. But if your "self" is a person who's anxious about talking to people or afraid of rejection, throwing caution to the wind for an attractive stranger can be daunting, to say the least — especially if you're the one putting yourself out there or initiating the hookup. "If you’re shy or socially anxious it can be especially hard to ask someone out," says Paulette Sherman, PsyD, a New York City-based psychologist and author of Dating from the Inside Out. "You may already be extra hard on yourself and will berate yourself if you get rejected, further plummeting your self-esteem."
But that doesn't mean you should abandon all hopes of having the sun-soaked hookup you want. In fact, Dr. Sherman says it might be easier than you think, but it might take a little trial and error. And as weird as it sounds in the world of flings, you might just need some practice.
Thankfully, flings are generally low-stakes, and if things go awry, well, it actually might be a good place to practice how to approach a relationship (even if it's meant to be a short-lived one).
"You may want [a fling] to be with a person who is nice to you, but it doesn’t have to create a permanent change in your life," Dr. Sherman says. "Knowing this might make you less nervous about the outcome of all your actions or of embarrassing yourself."

The expectations around having a fling are to have few expectations and to enjoy the moment.

Paulette Sherman, PsyD
If it doesn't, Dr. Sherman has some tips that you can keep in mind — some of them might be things that you're already doing. For instance, she says her shy clients like to meet people on dating apps, through mutual friends, or in a group class setting, like a pottery class or group fitness class.
"On an app, they can patch themselves up to meet someone somewhere they feel comfortable at a time of their choice, so they have some control there," she says. "Plus, if they don’t like them, they never have to see them again."
And if you prefer an IRL meet-cute through a mutual friend or in a class, you already have something in common to talk about. (And hopefully, your mutual friend can play matchmaker.)
But should you spot someone in real life who you're instantly attracted to, taking the plunge to talk to them may not be as complicated as you think.
"You can break the ice by just smiling and saying hi," Dr. Sherman says. "Usually if the other person is interested, they can grab the ball from there and reciprocate, especially if you are the shy one."
And if they aren't interested? Well, that might have to be the "error" part of your trial and error. What's important is that you don't psych yourself out of initiating a fling in the future.
"The expectations around having a fling are to have few expectations and to enjoy the moment," Dr. Sherman says. "This can be hard for an anxious person to do, because it can entail a certain amount of surrender, [but] it may help them to remind themselves that, since they aren’t trying to build a long term relationship, they can just have fun and experience things without too many repercussions."
With that in mind, maybe the most important part of having a summer hookup is to not take it too seriously, whether you perfectly execute a pick-up line or you flub up and strike out.

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