Milano plays Rebecca Thomas, a recently divorced single mom attorney in Pittsburgh who hasn't dated "since Bill Clinton was president".

[9] Initially titled Threesome, the pilot revolved around a single 30-something man who is caught between his lazy best friend roommate and his single-mother girlfriend.

Our creative showrunner is Ricky Blitt from Family Guy and I was struck at how funny the female characters were written.

[13] At the end of March, ABC announced the show as Single With Baggage in its 2009 program development guide,[4] and finally as Romantically Challenged in May.

Director Burrows also endorsed Pittsburgh since his positive experience filming parts of the former sitcom Back to You in the city.

An Entertainment Weekly critic wrote of the opening episodes: "At times relatably funny: The rules of one-night stands can be fairly confusing.

Others were praising the performance of Milano but gave a negative review of the show, like USA Today: "As terrible as Romantically is, it is in the end more puzzling than insulting.

[24] Although a reasonable amount at another timeslot, the show's future was already feared to be cut short due to its lead-in from Dancing with the Stars, which captured 20.8 million viewers.