In each episode of flirtations and fails, one real-life single navigates five blind dates. The mission: Find one match worthy of a second date.
Dating Around (Season 1)

Luke (Episode 1)
Air date: 2019-02-14
Runtime: 29 min
Overview: He may be a ladies' man, but Luke is ready to settle down -- after some light drinking, deep kissing and one date's awkward-but-adorable door snafu.

Gurki (Episode 2)
Air date: 2019-02-14
Runtime: 26 min
Overview: Fiercely independent Gurki is eager to open up about divorce, until one date radically challenges her candor. Will she back down or speak her mind?

Lex (Episode 3)
Air date: 2019-02-14
Runtime: 26 min
Overview: Production designer and mustache aficionado Lex is a master of cool, cultured charm. But can he defuse one man's awkward second-date invitation?

Leonard (Episode 4)
Air date: 2019-02-14
Runtime: 29 min
Overview: What does love look like after loss? Sweet and sophisticated widower Leonard is ready to find out -- and try his hand at an impromptu dance lesson.

Sarah (Episode 5)
Air date: 2019-02-14
Runtime: 26 min
Overview: She’s got a thing for a quick wit. But will tech recruiter Sarah find a genuine connection after dinner conversation takes an unexpected turn?

Mila (Episode 6)
Air date: 2019-02-14
Runtime: 24 min
Overview: Mila knows the ropes of NYC fashion, but she’s brand-new to NYC dating. Will her fresh take serve as a turnoff or seal the deal with the right lady?
