Jack "Gator" Gately goes on a surprising blind date, Kate dates an employee of the Boston Celtics basketball team, and Freddy learns that romance often comes with a price tag attached.
Gator's new girlfriend has a minor physical imperfection, but as small as it is, he can't help being repulsed. Kate begins seeing a "musician," and Freddy starts hanging out with a bouncer.
Gator and Freddy meet two beautiful ladies from Iceland, which makes Gator think he can relive the glory of his college years. Kate convinces Tommy to accompany her to a children's party when she discovers that her ex will be attending.
Gator meets a woman inside a boxing ring, after joining a gym. Meanwhile, a coworker's exercise habits are questioned by Kate, and Tommy receives intimacy lessons from Freddy.
Gator's new assistant has an admirer in Kate. Online dating links Freddie with a face from his past. Also, Tommy falls in love while working on jury duty.
Gator schemes to appear as if he change his ways to get a date with an animal rights activist. Kate opts for a different dating pool, and Freddy is given driving lessons from Tommy.