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 what’s wrong with all the people you will definitely meet on Tinder in New York or trying to hit it off between shots at one of New York’s best hookup bars, it takes a lot of legwork to get your legs up in this town. So each week, 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

Michael and Austin
Sex and dating

Michael and Austin

Matt and Caitlin
Sex and dating

Matt and Caitlin

Sarah and Sam
Sex and dating

Sarah and Sam

Matt and Cara
Sex and dating

Matt and Cara

Natalie and Matt
Sex and dating

Natalie and Matt

Michael and Kyle
Sex and dating

Michael and Kyle

Juliana and Andrew
Sex and dating

Juliana and Andrew

Matt and Krista
Sex and dating

Matt and Krista

Wandi and Sam
Sex and dating

Wandi and Sam

Meredith and Craig
Sex and dating

Meredith and Craig

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After the date

A classic fade-out
News

A classic fade-out

A terrible second date
News

A terrible second date

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