Meet Pleasantville, NY singles at a live online event

Join our hosts for games, prizes, and speed dates while MatchMaker learns what you’re looking for.

Jessica, a Couple member near Pleasantville
Jessica, 56
Woman · Pleasantville, NY
Top interests
Hiking Traveling Arts and crafts

Our next four online events

Join from anywhere near Pleasantville. Every mixer has friendly hosts, group games, and video speed dates … all while MatchMaker, our AI Cupid, works behind the scenes to find you your most compatible matches.

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Find local love in Pleasantville

Pleasantville, NY is a small-town oasis that's perfect for romantic rendezvous! Stroll hand-in-hand through the charming downtown, where you'll find a plethora of cozy cafes, quirky shops, and delightful eateries. Sparks will fly as you explore this picturesque village together.

Take your love affair beyond Pleasantville's borders and discover nearby attractions for an idyllic date. Wine and dine in Tarrytown or embark on a scenic hike in the Rockefeller State Park Preserve. You'll be smitten in no time with the endless charm of Westchester County!

First date ideas in Pleasantville

Already clicked with someone? Take it offline with one of these Pleasantville spots.

Rockefeller State Park Preserve
Rockefeller State Park Preserve
125 Phelps Way, Pleasantville, NY 10570-3500
Rockwood Hall State Park
Rockwood Hall State Park
Phelps Way, Sleepy Hollow, NY 10570
Jacob Burns Film Center
Jacob Burns Film Center
405 Manville Rd, Pleasantville, NY 10570-2825

MatchMaker helps you meet singles from Pleasantville and beyond

Whether you’re looking for a date across the street or across the country, Couple has you covered. MatchMaker gets to know you and what you’re looking for, and finds your most meaningful matches from Pleasantville or wherever you’re looking. The more events you attend, the stronger your matches get.

Join us for fun games, prizes, and speed dates at our virtual or in-person get-togethers. If you’d prefer to venture just outside Pleasantville, explore the nearby towns below.

Meet singles from
towns near Pleasantville