The Undateables

We take two undateable New Yorkers and put our matchmaking skills to the test

The Undateables

Everyone knows it can be tough to be single in New York. Whether you’re trying to figure out some actually good cheap date ideas in NYC or hit it off at one of New York’s most romantic bars or restaurants, it takes a lot of legwork to meet the perfect one in this town. So twice a month, we try to help two single New Yorkers who think they’re totally undateable. We pair them up and send them out to have (we hope) a fun, romantic night on the town. Afterward, we find out what went well on the date, and what went horribly, horribly wrong.

Do you want to get set up on a free blind date? Email undateable@timeout.com.

The Undateables

Eliza and Luke
Sex and dating

Eliza and Luke

Megan and Alex
Sex and dating

Megan and Alex

Orlando and Renée
Sex and dating

Orlando and Renée

John and Davis
Sex and dating

John and Davis

Advertising
David and Maura
Sex and dating

David and Maura

 Luke and Viviana
Sex and dating

Luke and Viviana

James and Annabelle
Sex and dating

James and Annabelle

David and Barrie
Sex and dating

David and Barrie

Courtney and Maggie
Sex and dating

Courtney and Maggie

Aliyah and Ryan
Sex and dating

Aliyah and Ryan

Show more

Round two dates

Michael and Devon
Sex and dating

Michael and Devon

Lauren and Tyler
Sex and dating

Lauren and Tyler

Sarah and James
Sex and dating

Sarah and James

After the date

Recognized on Tinder
News

Recognized on Tinder