S1 • E1
Natalia and Skip - UncensoredBig Jay Oakerson does his best to hook up Natalia, who's normally drawn to guys who aren't interested in her, with his college buddy Skip.09/21/2015
S1 • E2
Eli and Kitty - UncensoredBig Jay Oakerson introduces a nerd named Eli to tatted-up cool girl Kitty to find out if they're a match made in Tatooine.09/28/2015
S1 • E3
Keifer and Julia - UncensoredBig Jay Oakerson sets up mild-mannered Keifer on a date with a woman named Julia and sees if sparks fly when they're challenged to write poems about each other.10/05/2015
About Lucky Loser Season 1
Big Jay Oakerson brings his famous on-stage matchmaking skills out into the real world in a quest to find a perfect mate for people on a romantic losing streak.