Bruce sets his sights on Jessica, a single mom, who proves to be more challenging than expected. Liv feels so alive with Ron that she starts behaving out of character. Maya fends off advances from some Hawaiians that think she is one of their own.

Hopeless romantics and frequently heart-broken, Cal and Kacey seem perfect for each other, but Bruce has other ideas and tries to keep his friend from being a four time loser in love. Liv's wild night continues as she decides to give her panties to Ron while Jessica and Fab decide to engage in a friendly competition.

Jessica and Fab compete for Dominic, the bartender. Bruce, Cal and Tom can no longer get any service from Kacey, who is upset with Cal, so the guys risk giving up their table to move to a booth. Liv is shocked when she learns something intimate about Ron.

Tom and Maya are hitting it off well, to the amazement of Bruce and Cal when trouble enters the bar in the form of Tom's ex-girlfriend. Liv makes friends with Jessica and Fab and asks for their advice with meeting guys. A group of firemen enter the bar and charm the ladies but Ron is in no mood to surrender.

Bruce and Fab's intense dislike of each other lead to a bizarre bonding moment. Tom becomes the talk of bar and gains respect by accident. Liv and Maya track down the owner of a picture of a well endowed package.

Jessica sets out to retrieve a delicate photo of herself from Ron's phone and ends up remembering how much she likes him. Maya talks to a man who thinks she is something she is not while Bruce searches for a woman who likes redheads.

Kacey gives Dominic an ultimatum about their relationship and is surprised by his answer. Dominic then seeks Tom's advice as to what he just agreed to. An intoxicated Liv is out of control and consumed with jealousy over Ron and Jessica.

After being caught at the bar by her fiancee, Liv tries to win Jim back. Bruce learns Tom and Cal sometimes choose not to hang out with him and it hurts his feelings.

The night is late and Bruce has yet to seal the deal with Jessica, so he decides to try something clever. Fab and Kacey both notice their handsome gynecologist and must decide which one of them gets to make a play for him. Liv and Ron decide to do something crazy and leave for a strip club.

Last call induces panic among those who have not locked up someone to go home with. As Tom tries to finalize Maya, he finds himself drawn to Liv, while Liv is having second thoughts about Ron while seeing Tom in a new light. Meanwhile, Bruce strikes out with Jessica and is stuck looking for a fallback.

It's closing time and Tom takes Bruce and Cal's advice to not waste time getting Maya home in case she changes her mind, but a surprise awaits him anyway. Bruce must decide whether to take one last crack at Jessica or go home with the girl who likes redheads. Kacey has second thoughts about Cal while Liv does the same with Ron.