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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.

24
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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  • Check out the Top Hamptons Events This Weekend!

✨ Weekend Events in the Hamptons ✨

🇬🇷 Hamptons Greek Festival
📅 July 16–23 | 🕓 4 PM – 11 PM
📍 Dormition of the Virgin Mary Cathedral, Southampton
Enjoy authentic Greek food, pastries, live music, and traditional dance performances.

🧘 Yoga in the Vines
📅 July 18 | 🕗 8 AM
📍 Wölffer Wine Stand, Sagaponack
Start your morning with yoga surrounded by beautiful vineyard views.

🎡 CMEE’s 16th Annual Family Fair
📅 July 18 | 🕤 9:30 AM – 12 PM
📍 CMEE, Bridgehampton
Arts & crafts, water play, food trucks, live entertainment, candy, and family fun with this year’s Endless Summer theme.

🎨 Art in the Park
📅 July 18–19 | 🕙 10 AM – 5 PM
📍 Agawam Park, Southampton
Browse paintings, photography, sculptures, and more from over 50 local artists.

🎸 The Telescreens Live
📅 July 18 | 🕗 8 PM
📍 Stephen Talkhouse, Amagansett
Enjoy an evening of rock and pop at one of the Hamptons’ most iconic music venues.

🎷 Hamptons Jazz Fest
📅 July 18 | 🕕 6 PM
📍 The Church, Sag Harbor
The Rez Abbasi & Kiran Ahluwalia Quartet perform an unforgettable night of jazz.

🖼️ Harlem Fine Arts Show Summer Festival
📅 July 17–19
📍 Duck Walk Vineyards, Water Mill
Explore immersive art galleries, celebrity chef experiences, live music, luxury cars, and more.

💄 Armani Beauty Pop-Up
📅 July 17–18 | 🕚 11 AM – 5 PM
📍 The Surf Lodge, Montauk
Experience beauty touch-ups, exclusive gifts, and immersive makeup experiences.

👨‍🍳 Stirring the Pot: Chef Kwame Onwuachi
📅 July 19 | 🕚 11 AM
📍 Guild Hall, East Hampton
A conversation with acclaimed chef and author Kwame Onwuachi, hosted by Florence Fabricant.

📚 Fridays at Five: Elaine Sciolino
📅 July 17 | 🕔 5 PM
📍 Bridgehampton Library
Hear the bestselling author discuss Adventures in the Louvre.

🎤 Matisyahu Live
📅 July 18 | 🕓 4 PM – 11 PM
📍 Solé East Resort, Montauk
Enjoy an outdoor performance featuring fan favorites and career-spanning hits.

🥾 Cedar Point County Park Hike
📅 July 19 | 🕙 10 AM – 12 PM
📍 East Hampton
Join the East Hampton Trails Preservation Society for a guided nature hike.

Check out more events at Hamptons.com 

#hamptons #weekend #easthampton #montauk
  • Cooper’s Beach was named the #1 beach in America by Dr. Stephen P. Leatherman (aka Dr. Beach), geoscientist and founder of the National Healthy Beaches Campaign. 

Cooper’s Beach has it all: chair and umbrella rentals, an oceanfront cafe, and one of the best views in the Hamptons. We stopped by last night to watch the Lone Sharks perform as part of the Southampton Cultural Center’s Summer Concert Series, a perfect way to spend a summer evening.
#Coopersbeach #beach #music
  • The 28th Annual Rell Sunn Surf Competition returned to Ditch Plains in Montauk on July 11th. One of Montauk’s longest-running surf traditions, the event brings together the local surf community while raising funds for Shred the Love, this year’s official nonprofit partner supporting local community members and families in need in Montauk.
#Surf #surfcontest #waves #fundraiser #mtk
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#Montauk #Vintage
  • Any reason to visit @montaukyachtclub is a good one, especially when there’s great art from @joehenrybaker, @stgermaindrinks cocktails, and a “killa” pair of new shades from @akila.la.

The beachfront ballroom recently hosted an exhibition of Joe Henry Baker’s large-scale abstract works: muted, tactile, and calming without disappearing into the room. Hot take: replace the enormous black rectangle above your fireplace—sometimes called a TV—with one of his pieces. The evening also marked the start of AKILA Eyewear’s summer pop-up, with handmade, adventure-ready frames that are polished enough for the Hamptons but practical enough to enjoy wearing.

Life—and art—just looks better through a pair of AKILA sunglasses.

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  • What started as a personal idea rooted in love and connection has evolved into a refined jewelry brand that blends meaning with timeless design. Founded by Melanie Bronfman, Stella James was created to offer something more than traditional fine jewelry with pieces that feel personal and meaningful while maintaining an elevated aesthetic meant to be worn every day.⁠
⁠
Inspired by both New York’s sophistication and the relaxed elegance of the Hamptons, the brand balances strength and softness. Signature diamond letter pieces have become a defining element of the collection, designed to represent identity, memory, and the people we carry with us.⁠
⁠
As Stella James continues to grow, Melanie remains focused on craftsmanship, storytelling, and creating pieces that feel both modern and lasting. She spoke more about the inspiration behind the brand, her design philosophy, and how Stella James fits seamlessly into everyday style from city life to summer days out East.⁠
⁠
Can you share the story behind Stella James, when you launched, and what inspired you to create the brand?⁠
⁠
MB: Stella James was born from a deeply personal place. I wanted to create something that allowed me to carry a symbol of the people I love most with me, every day. What began as a personal idea designing a meaningful piece tied to my children evolved into a brand rooted in emotion, craftsmanship, and timeless design. We launched with the intention of creating jewelry that doesn’t just look beautiful, but feels significant.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#stellajames #jewelry #hamptons
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