Join or Sign In

Sign in to customize your TV listings

Continue with Facebook Continue with email

By joining TV Guide, you agree to our Terms of Use and acknowledge the data practices in our Privacy Policy.

Romantically Challenged Season 1 Episodes

Season 1 Episode Guide

Season 1

6 Episodes 2010 - 2010

A newly single mom, Rebecca Thomas (Alyssa Milano) re-enters the dating pool, and looks to her equally romantically-challenged friends Perry (Kyle Bornheimer), Shawn (Josh Lawson), and Lisa (Kelly Stables) for advice and support as she makes the transition back into the dating world and must become the primary bread winner along the way.

Episode 1

Don't Be Yourself

Mon, Apr 19, 2010 28 mins

In the opener of this ensemble comedy about four friends' hapless love lives, Perry (Kyle Bornheimer) has a problem with bedroom banter, and Rebecca (Alyssa Milano) rushes into romance when she learns that her ex is remarrying.

Where to Watch
Romantically Challenged, Season 1 Episode 1 image

Episode 2

The Charade

Mon, Apr 26, 2010 28 mins

Rebecca meddles in Lisa's love life, and Lisa finds a way to get payback. Meanwhile, a pretty girl short-circuits Shawn's attempt to pick up roommate Perry after gum surgery, and Perry kicks him out of the apartment.

Where to Watch
Romantically Challenged, Season 1 Episode 2 image

Episode 3

Perry and Rebecca's High School Reunion

Mon, May 3, 2010 28 mins

Rebecca and Perry attend their high-school reunion, where a prom-night humiliation haunts Rebecca. Meanwhile, Shawn romances Lisa's friend Vanessa because her cable system carries the hockey championship games and his system doesn't.

Where to Watch
Romantically Challenged, Season 1 Episode 3 image

Episode 4

Rebecca's One Night Stand

Mon, May 17, 2010 28 mins

Lisa convinces Rebecca to try a one-night stand. Meanwhile, Perry takes a stay-at-home vacation, which irritates unemployed roommate Shawn so much that Shawn is willing to take a job---virtually any job.

Where to Watch
Romantically Challenged, Season 1 Episode 4 image

Episode 5

Perry Dates His Assistant

28 mins

Rebecca sees potential in her date---until she sees the tattoo on his chest. Meanwhile, Perry tries to fire his assistant (Anna Camp) but unwillingly winds up in a relationship with her instead; and Shawn is reluctant to dog-sit for a coworker before he learns that the pooch is a babe magnet.

Where to Watch

Episode 6

Hey Now, Hey Now, Perry's Girlfriend's Back

28 mins

Where to Watch