Henry Beckman was living the perfect life - until his girlfriend, Heather, convinced him to move to Chicago to work for her uncle. Now she's dumped him, he's out of work, and living with a very outspoken roommate who has his own surreal opinions on life and women.
Henry reveals he still has the engagement ring he intended to give his ex-girlfriend Heather before she broke up with him. Larry pressures Henry to sell the ring online to pay for a wine refrigerator. Amanda borrows Henry's ring to impress a guy she used to date but hasn't seen in years. Meanwhile, the gang is surprised to find out that Tina popped the question to Brad, but has yet to receive a ring from him since they got engaged.