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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.

18
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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The USGA has crafted the ultimate fan experience for the 126th U.S. Open Championship, held at the historic Shinnecock Hills Golf Club, with elevated activations taking place now through June 21st.

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A Seat at the Table

A Seat at the Table

  • Golden hour just got a little sweeter 🍋☀️ Fishers Island Lemonade is back at the iconic Clam Bar in Amagansett. Last Saturday they hosted a special weekend pop-up with drinks and custom embroidery. Stop by for fresh oysters and refreshing Fishers Island Lemonade. The perfect way to kick off summer in the Hamptons. #hamptons #lemonade #clambar
  • On Friday, June 12th, the U.S. Open Championship Trophy arrived at the new Shinnecock Hills Station on the Long Island Rail Road (LIRR). President of the Long Island Rail Road Robert Free accompanied the trophy aboard the LIRR and was welcomed by USGA Senior Director Eric Steimer at the station.⁠
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#usopen #golf⁠
#golfcourse #golfing #shinnecockhills
  • Rooted in sustainability, community, and exploration Amber Waves Farm is a place where people connect with the land, learn where their food comes from, and help preserve local agriculture for future generations. From educating aspiring farmers to supporting food security and protecting open farmland, Amber Waves continues to grow stronger one harvest at a time 🌱 #hamptons #farms
  • Check Out the Top Hamptons Events This Weekend!

🥃 World Cup Celebration with Clase Azul
📅 Pushed to July 10th
📍 Si Si
Enjoy Clase Azul tequila tastings, light bites, personalized engraved decanters, and a World Cup match.

🍷 ARF’s Rescues & Rosé
📅 Friday, June 12 | 6–9 PM
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📅 Saturday, June 13 | 8:30 PM
📍 Amagansett Square
Grab dinner from your favorite local spots and cheer on the Knicks during the NBA Finals.

🌹 Southampton Rose Society Annual Rose Show & Rose Day Celebration
📅 Saturday, June 13 | 7:30 AM–4 PM
📍 Rogers Memorial Library
See stunning rose displays throughout Southampton!

🎡 LVIS Annual Fair
📅 Saturday, June 13 | 10 AM–4 PM
📍 Ladies’ Village Improvement Society
Celebrate America’s 250th anniversary with family-friendly activities, live entertainment, shopping, food trucks, and more.

🎨 Meet the Artist Series with Julia Scheuer
📅 Saturday, June 13 | 2–4 PM
📍 Gallery 908
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Enjoy pilates, wellness activations, food, drinks, a cold plunge, and sauna experiences.

👜 2nd Annual Hamptons Handbag Festival
📅 Sunday, June 14 | 10 AM–5 PM
📍 15 Montauk Highway, Amagansett
Shop designer, luxury, vintage, and one-of-a-kind handbags and hear from notable collectors and curators.

🖼️ Community Day at the Parrish Art Museum
📅 Sunday, June 14 | 11 AM–5 PM
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Enjoy free admission, artist-led workshops, exhibition tours, and a local artisan market.

🎶 Prospa at The Surf Lodge
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⛳ 126th U.S. Open Championship
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Check out more events at Hamptons.com (Link in Bio)
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#usopen #art #knicks #amagansett #tequila
  • Kith and Vivrelle have collaborated on a summer pop-up in Bridgehampton, bringing together contemporary fashion and luxury accessory rentals in a single retail experience. ⁠
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Running now through Labor Day, the store showcases Kith Women’s latest seasonal collections while introducing shoppers to Vivrelle’s membership-based model for borrowing designer handbags and jewelry. The partnership is designed to appeal to Hamptons visitors looking for a curated and elevated shopping experience that blends fashion, lifestyle, and convenience.⁠
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