Jack "Gator" Gately finds himself ill-prepared to re-enter the dating scene as a blind date goes bananas for him; his friend and neighbor Kate finds big things come in small packages when she dates a member of the Boston Celtics; and Indian-born Dr. Freddy learns that love isn't cheap with the woman of your dreams.
Gator is hung up on his new girlfriend's minor physical flaw, leading Tommy to take drastic measures. Freddy befriends a bouncer; Kate dates a musician whose talents are not what they seem.
Gator tries to relive his college drinking and glory days, when he and Freddy meet two attractive Icelandic women. Meanwhile, Kate plans to drag Tommy to a children's birthday party, until she learns her ex will be there.
Gator joins Kate's boxing gym only to be challenged by a woman in the ring, and Kate confronts a co-worker who lets it all hang out in the locker room. Freddy teaches Tommy tantric sex methods.
Gator and Kate are both handicapped when Kate begins dating his new assistant. Freddy reconnects with his ex when he attempts online dating. Tommy finds love at jury duty.
Gator woos his new neighbor, an animal-rights activist, while Kate dates an exterminator. Meanwhile, Tommy teaches Freddy how to drive.