Mega Mixer alert: Tons of matches, $3K in prizes! Thu. 10/29 @ 7:30PM ET! Mega Mixer Thu. 10/29 @ 7:30PM ET — $3K in prizes!

Meet Annapolis, MD singles at a live online event

Enjoy comedy, games, and speed dates while MatchMaker learns what you’re looking for.

Tosha, a Couple member near Annapolis
Tosha, 42
Woman · Annapolis, MD
Top interests
Board games Bowling Dancing

Our next four online events

Join from anywhere near Annapolis. Every mixer has real 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 Annapolis

Ahoy, lovebirds! Your romantic voyage awaits in Annapolis, MD, where the sea of love meets history's charming shores. Sail away on a cozy sunset cruise and swoon under the starry sky or take your darling on a dreamy stroll through the brick-lined streets of downtown Annapolis.

Add a splash of fun to your tryst by exploring the nearby Chesapeake Bay, or let your love bloom at the lush Quiet Waters Park. For an artsy twist, enjoy an intimate show at the Annapolis Shakespeare Company. So set sail, mateys, and embark on your Annapolis amour adventure!

First date ideas in Annapolis

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

The Colonial Players
The Colonial Players
108 East St, Annapolis, MD 21401-1710

MatchMaker helps you meet singles from Annapolis 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 Annapolis 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 Annapolis, explore the nearby towns below.

Meet singles from
towns near Annapolis