Harry Connick Jr is a well known musician who's recently split with his girlfriend Emily. In an effort to get him to realise there are other women out there, and also to get some free promotion his manager and friend Keith puts him forward to take part in a charity edition of a dating reality show. Jennifer Lopez is a young single mother to a 19 month old son and hasn't been dating since the split from her son's father. Her room-mate and best friend Leah decides to put her forward to take part in the charity edition of the show to make her friend at least dip her toes in the dating game once more. Will Jennifer let herself get involved in love again and could they have a real relationship if Jennifer is keeping the most important thing in her life a secret? Not to mention inter-office relationships heating up between herself and one of her employers.