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This one is, well, as described.  Alyssa is great in this though.  Here is the ABC data sheet, I couldn't not make some comments... Enjoy! 

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 (why Clinton is the marker here makes this instantly uncomfortable,  but I digress) -- 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  (Perfect Plan!). 

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 (Why?) After 40 minutes, he's already naming their future children. (Cringe)  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 (go on...), and sees a "threesome" as "second base." (Queen!).  

Will these four romantically challenged friends ever find lasting love? Or even someone who lasts until next Thursday? (insert chuckle here)

Files

Romantically Challenged - Unaired 2008 Pilot (Director's Cut)

Alyssa Milano, Kyle Bornheimer, Josh Lawson, Israel Broussard, Valorie Hubbard, Nicole Pettis Directed by James Burrows After Rebecca learns about her ex-husband's impending wedding, she decides to jump headfirst into the dating pool. But the crew get her so worked up that, when it comes time to the actual date, she becomes flustered and ends up saying some ridiculous things about herself. Meanwhile Perry meets a girl he thinks is perfect - until he finds out she likes to be talked dirty to during their romantic encounters, so Lisa takes it upon herself to coach Perry through Dirty Talk 101; and Rebecca enlists struggling and unpublished writer Shawn to help her son, Justin, write a story for his high school English class. This series DID air, just had a slightly different pilot (don't they all)...Blueprints aren't subject to change, they are intended too!

Comments

LifeIsStrange

I hope the unaired episodes turn up someday

Anonymous

Here’s the script for the original version of the pilot (don’t know if it was filmed or not) which has the Eric Christian Olsen as the center and is based on his romance with Milano's character. Odd pivot. It's by Ricky Britt, who wrote the previously featured SINGLE WHITE MILLIONAIRE.