Romantically Challenged

TV review by
Kari Croop, Common Sense Media
Romantically Challenged TV Poster Image
Weak comedy mines laughs from single mom's sex life.

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A lot or a little?

The parents' guide to what's in this TV show.

Positive Messages

The show paints casual sex as a rite of passage and places little emphasis on the characters' professional (or deeply personal) lives. Most "lessons" are pretty glib.

Positive Role Models & Representations

The main characters aren't known for making great decisions. Rebecca sleeps with a stranger, and Lisa encourages her to do it. Shawn freeloads off of Perry, etc. Rebecca's role as a mother is hardly explored -- and neither is the effect her newfound sex life might have on her son.


Some heavy sexual innuendo, but there's rarely any action on camera. One character has her first one-night stand, etc.


Some gateway words like "ass," "hell" and more creative phrases like "piece of ass" or "you're his bitch."

Drinking, Drugs & Smoking

Adults drink socially on occasion in bars or restaurants, or at home.

What parents need to know

Parents need to know that the series deals with a divorced mother's attempt to reassert herself on the dating scene. Because of that, there's a healthy dose of sexual innuendo, but you won't actually see many sexual situations -- you'll just hear about them. Along with that, there's some gateway language like "bitch" and "ass" (and even phrases like "you're his bitch" and "piece of ass"). There's some social drinking, too, in the context of going to bars or entertaining at home.

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What's the story?

Divorced single mom Rebecca Thomas (Alyssa Milano) might be ROMANTICALLY CHALLENGED, but her sister, Lisa (Kelly Stables), is determined to guide her through the dating scene, even though Rebecca hasn't been out with anyone in more than a decade. While Lisa schools her sister on the rules of one-night stands and such, their mutual friends, Perry (Kyle Bornheimer) and Shawn (Josh Lawson), work out cohabitational kinks as platonic roommates.

Is it any good?

Although Romantically Challenged was created in part as a vehicle for her talents, Milano barely registers here, and it's not because she isn't good in it. It's mostly due to a flippant script that oddly ignores her character's complicated past (she's raising a son from a previous marriage and, apparently, is also a lawyer) and gives all the good one-liners to her likable co-stars. Stables, in particular, tends to run away with any scene she's in thanks to a charismatic blend of Megan Mullally and Kristin Chenoweth.

As a result, you care less about Milano's character, who's supposed to be holding it all together, and tend to notice curious details. Like the fact that we have no idea how these friends are acquainted (other than the fact that two of them are sisters), how most of them make a living or why they seem to spend all their time in a combination coffee shop/lunch spot that also serves wine. Finding romance again is challenging, but so is this comedy's half-baked premise.

Talk to your kids about ...

  • Families can talk about the show's reliance on sex and sexual topics for humor. What messages is it sending about sex and dating? Are those messages different for women versus men? Is there any attempt to talk about safe sex?

  • How do you think these characters became friends in the first place? What clues do you get from the script?

  • Do you think Rebecca is a positive role model? Does your opinion of her change when you find out she's also the mother of a teenager?

  • What kinds of stereotypes about women and men are portrayed on this show? Does this show do anything to challenge stereotypes, or does it reinforce them?

TV details

Our editors recommend

For kids who love comedy

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