The BEST Episodes of Dating Around
Every episode ever - ranked by fan votes!
Last Updated: Sep 21, 2021
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.
#1 - Ben
Season 2 - Episode 2 - Aired Jun 12, 2020
A unique "nice guy," Ben's been called "too good for this world." Now it's time to see if his matches agree - or if he's destined for the friend zone.
#2 - Justin
Season 2 - Episode 1 - Aired Jun 12, 2020
He's got smooth moves, swift jokes and a soft spot for his mama. Now Justin is ready for real romance - and an awkward round of guess my age.
#3 - Demi
Season 2 - Episode 6 - Aired Jun 12, 2020
She's a dynamic catch in search of a kind-hearted match. Will native New Yorker Demi finally find one - or will she fall for another bad boy?
#4 - Deva
Season 2 - Episode 3 - Aired Jun 12, 2020
Deva's an open book when it comes to art, identity and sexuality. Will one date's strict rules for intimacy ruin an evening of flirtatious fun?
#5 - Heather
Season 2 - Episode 4 - Aired Jun 12, 2020
She shares her heart and charms her suitors with honesty and confidence. But can Heater handle one beau's surprising hobby?
#6 - Luke
Season 1 - Episode 1 - Aired Feb 14, 2019
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.
#7 - Lex
Season 1 - Episode 3 - Aired Feb 14, 2019
Production designer and mustache aficionado Lex is a master of cool, cultured charm. But can he defuse one man's awkward second-date invitation?
#8 - Gurki
Season 1 - Episode 2 - Aired Feb 14, 2019
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?
#9 - Leonard
Season 1 - Episode 4 - Aired Feb 14, 2019
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.
#10 - Sarah
Season 1 - Episode 5 - Aired Feb 14, 2019
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?
#11 - Mila
Season 1 - Episode 6 - Aired Feb 14, 2019
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?
#12 - Brandon
Season 2 - Episode 5 - Aired Jun 12, 2020
All of Brandon's dates comes with surprises, from a dashing smile to a passion for cheese. But who will he pick when past, present and future collide?