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

Michael and Jaime
Sex and dating

Michael and Jaime

Molly and Tom
Sex and dating

Molly and Tom

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Miri and Margo
Sex and dating

Miri and Margo

Kris and Stacy
Sex and dating

Kris and Stacy

Michael and Dominick
Sex and dating

Michael and Dominick

Josh and Shannon
Sex and dating

Josh and Shannon

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Parker and Nick
Sex and dating

Parker and Nick

Effie and Alex
Sex and dating

Effie and Alex

Michael and Austin
Sex and dating

Michael and Austin

Matt and Caitlin
Sex and dating

Matt and Caitlin

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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

A classic fade-out
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A classic fade-out

A terrible second date
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A terrible second date

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