Tom Farrell, a music executive, looks for love in the big apple. While looking for love he is fired from his record company so attempts to start his own. Meanwhile, Tom's girlfriend pressures him to get married to her.

Tom promises to get a famous singer he once represented to play at a benefit concert, but her lable company will not let her even though she wants to. Meanwhile, Mike and Karen look for a nanny for their child.

Tom deals with a tight budget, quirky director and looming deadline as the record company films Wayne's first video.

Tom must represent his ex-girlfriend's band and discovers that they still have feelings for each other.

Tom has a small window of opportunity to promote the Barbarian Brother's latest album and a review from Abby Powell could take the band to the next level. However, as the band's rock star lifestyle spins out of the control and Abby makes her feelings for Tom known, Tom must find a way not sabotage both his career and love life. Meanwhile, Bran's relationship with Scott progresses until a pregnancy scare threatens to derail it.

Tom and the guys attend Carmine Moretti's, the owner of their favorite pizza place, funeral when Tom finds that Carmine's son Ray is an amazing singer and could be a star. But since Ray must now support his family and take over his father's business, Tom must convince Ray not to squander his talent and convince Jeff that Ray has more potential for greatness than the artist Julia wants to respresent. Meanwhile, when Shooter and Mike are mugged, they are both forced to deal with the situation in their own way.

Tom gets the chance to buy the catalogue of a singer who cracked under the pressure of the music business years ago and never completed his long-awaited sophomore album.