Ben and Danny gamble on their mom's love life.

Bonnie and her old boyfriend Brad are in competion for a huge listing so she decides to seduce him in order to beat him.

Ben and Riley make a bet concerning strangers in a bar and it leads to trouble at work for both of them: Riley sleeps with a stranger who becomes her new boss, and Ben sleeps with the wife of the man who's trying to purchase the bar where he works.

While looking for a new bar manager, Ben interviews his old crush Sam, and decides to get revenge on her for never noticing him in high school. But things don’t turn out as planned.

Ben discovers Tucker has been making extra cash by visiting a sperm bank. In order to help Tucker pick up a nurse at the bank, Ben agrees to donate his own sperm but quickly regrets his decision after a couple chooses his sample. Riley and Danny continue to fight while attempting to host their friend’s engagement party. Their moms, archenemies Bonnie and Jennifer, team up to get Riley and Danny back together.

After Emma accidentally pokes holes in Ben’s stash of condoms, Ben, Tucker and Danny all fear their girlfriends might be pregnant. They discreetly try to find out if there’s anything to worry about while the girls pretend to have pregnancy symptoms to get them to confess the truth.