Romantically Challenged poster
Seen it?

Romantically Challenged

TV·2010–2010·ABC·Comedy, Romance·30m·Created by Ricky Blitt

Not streaming in your region — see every region's options

Smart and beautiful Rebecca is recently divorced after 15 years of marriage. Having never really dated before she was married - and not having been on a date since Clinton was in office -- she finds it scary to start over now. Although a gifted mom and lawyer, she is clueless about dating and hopes to get some help from her equally romantically challenged friends. Perry is Rebecca's best friend since childhood. He is a rugged man's man and a tremendously successful financial planner -- but also one of Pittsburgh's most sensitive hopeless romantics. When it comes to matters of the heart, Perry is a romance-aholic who falls in love with women 20 minutes after meeting them. After 40 minutes, he's already naming their future children. A struggling novelist, the witty and affable Shawn has been Perry's best friend and rent-free roommate for six years. Shawn is the emotionally unavailable cynic to Perry's hopeless romantic. He has never had a relationship more serious than a three-night stand - and even those send him running for the door. Rounding out the group is Rebecca's petite, baby sister, Lisa. Behind her deceptively sweet appearance is a sassy pit bull ready to protect her older sister. Although a nurturing kindergarten teacher, she has a wild side too, and sees a "threesome" as "second base." Will these four romantically challenged friends ever find lasting love? Or even someone who lasts until next Thursday?

Cast

Shows like Romantically Challenged all similar shows

The closest matches on shared genres, ranked by match strength and popularity.

  1. 01Comedy·RomanceFriends1994–2004·NBCStreaming on HBO MaxSix young (20-something) people from New York City (Manhattan), on their own and struggling to survive in the real world, find the companionship, comfort and support they get from each other to be the perfect antidote…8.5Compare
  2. 02Comedy·Romance·DramaHow I Met Your Mother2005–2014·CBSStreaming on HuluHow I Met Your Mother is a comedy about Ted and how he fell in love.7.9Compare
  3. 03Comedy·Romance·DramaGilmore Girls2000–2007·The CWStreaming on NetflixGilmore Girls is a drama centering around the relationship between a thirtysomething single mother and her teen daughter living in Stars Hollow, Connecticut.8.1Compare
  4. 04Comedy·RomanceYounger2015–2021·Paramount+Streaming on NetflixYounger follows 40-year old Liza, a suddenly single mother who tries to get back into the working world, only to find it's nearly impossible to start at the bottom at her age.7.3Compare
  5. 05Comedy·Romance·DramaHacks2021–2026Streaming on HBO MaxHacks explores a dark mentorship that forms between Deborah Vance, a legendary Las Vegas comedian, and an entitled, outcast 25-year-old.7.4Compare
  6. 06Comedy·Romance·DramaRivals2024–present·Disney+Streaming on Disney PlusRivals dives headfirst into the cut-throat world of independent television in 1986, where the shoulder pads are big and ambitions even bigger.6.2Compare

Head-to-head pick any opponent

Stack Romantically Challenged's full episode-rating history against a rival, on one chart.

Keep exploring top shows