Meet Oakland, MD singles at a live online event

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

Troy, a Couple member near Oakland
Troy, 55
Man · Oakland, MD
Top interests
Camping Dancing Hiking

Our next four online events

Join from anywhere near Oakland. 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.

See the full schedule

Find local love in Oakland

Tucked away in the serene mountains, dating in Oakland, MD promises a cozy and enchanting escape. Discover the town's charm hand-in-hand, with small-town treasures and heartfelt moments around every corner.

Get lost together in the breathtaking beauty of Deep Creek Lake, only a short drive away. Or, explore nearby Swallow Falls State Park for an adventure that'll make your hearts race and your love story truly unforgettable. Your Oakland romance awaits, so get ready to create memories that'll last a lifetime!

First date ideas in Oakland

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

Garrett County Museum of Transportation
Garrett County Museum of Transportation
107 S 2nd St, Oakland, MD 21550-1519
Sipside Lounge
Sipside Lounge
119 S 2nd St, Oakland, MD 21550-1519

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

Meet singles from
towns near Oakland