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Hamptons.com
May 21, 2026

Rules of the (Casual Dating) Game

It’s always good to keep things real, especially when it comes to dipping your toes in the dating pool. This is the season for fun in the sun, but are your expectations for meeting a potential partner in check? Here are five ways you set yourself up for a flirty fling—or something more.

21
VIEWS
Spotlight Teamby Spotlight Team
in Spotlight Magazine
Home Spotlight Magazine

By: Lindsey Met

 

 

Summer has almost arrived! And while the weather may not be as hot as we’d like it to be just yet, dating is hot as ever. Grease famously taught us “Summer lovin’/Had me a blast,” and unfortunately that hasn’t changed a bit. This season will always be associated with those short fleeting flings. Is it possible for things to last longer when you’re involved in a summer fling? Definitely. But in the meantime, we have to be realistic. Here are the best ways to stay grounded when it comes to your casual rendezvous this season.

 

1. Treat Them Like a Friend.

 

The best first-date advice I’ve ever gotten, and that I still give to this day, is go in expecting to make a new friend. If you make a new friend, no one gets hurt. If your mindset is that I can be friends with this person, you’re more relaxed, calm, and collected. You’re also curious and seeking to understand, rather than be understood. This is the best footing for dating, but especially casual dating.

 

2. Be Honest About Your Needs.

 

There’s always a way to disclose your needs without seeming needy or coming off like you want more. When I was first dating my husband, I told him that when we decided to sleep together I wanted him to spend the night. No expectations, just being clear about what would make me feel good. You have every right to say what you need in this situation, and a good person will respect that.

 

3. Decide Your Boundaries.

 

Are you strictly meeting up in public? Or will sleepovers be involved? It’s a great idea to figure this out early on, especially before feelings are involved. That way you protect yourself if feelings do creep into the picture later on. You’ve already established what you’re okay with—and the earlier you do that, the better.

 

4. Keep Your Options Open.

 

Like any casual dating situation, you must recognize that you’re not putting your eggs in one specific basket. If, and especially if, you’re wanting something more serious, it’s important to keep your options open so you don’t commit to your casual fling and miss out on a potential serious partnership that may be good for you. If you end up getting serious with someone else, make sure you’re transparent with your casual fling about it, because you would want that in return.

 

5. Don’t Force an Awkward Conversation.

 

As Kyle Cooke on Bravo’s Summer House says, “Summer should be fun.” Make sure you remember not to take any of it too seriously. That means not cornering your summer fling into an uncomfortable “What are we?” conversation, but rather leaning into riding the waves that the season has to offer.

 

 

You deserve to have an amazing summer, and you deserve to feel good about yourself, too! If anyone ever makes you feel otherwise, they aren’t the person—or even the fling—for you. For more dating, relationship, and motherhood tips, you can follow @wemetatacme on Instagram or check out “We Met At Acme” wherever you listen to podcasts.

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  • A Montauk sunset, endless summer energy, and Guy Gerber setting the soundtrack at The Surf Lodge. 🌊☀️ #guygerber #thesurflodge #montauk
  • Rounds at the U.S. Open ⛳️

Following Ryuichi Oiwa, Robbie Higgins, and Cooper Dossey as they tee it up on one of golf’s biggest stages.

#usopen #golf #shinnecockhills #southampton #golfclub
  • Check Out The Top Hamptons Events this Weekend

⛳ 126th U.S. Open Championship
📅 Now through Sunday, June 21
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The world’s top golfers return to historic Shinnecock Hills for one of golf’s most prestigious championships.

📚 Stirring the Pot: Padma Lakshmi
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Join Padma Lakshmi for a conversation about her new cookbook, All America: Tales, Travels and Recipes from Taste the Nation and Beyond.

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📅 Saturday, June 20 | 5 PM
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Enjoy rosé, live music, vineyard views, and a stunning Hamptons sunset.

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Spend an evening laughing with acclaimed comedian Elon Gold.

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Check out more events at Hamptons.com (Link in Bio)
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