When Alex encourages Mark to recycle his beer can, Mark takes an unusually firm stance against it, causing the two to "break-up." Trying to cheer Alex up, Whitney steps in for guy's night out, only to run into Mark and his new best friend, Neal. In an effort to reunite the bro-mance, Whitney, following advice from Lily and Roxanne, arms herself with some Rocky Road and red wine and sets out to discover the real root of Mark's heartbreak.

When Whitney and Alex go on a double date with Roxanne, Whitney is surprised to learn that Alex had a full life before he met her. In an effort to do more things together, they decide to play a friendly game of basketball, but things go awry and a sore loser emerges shocking the gang. Meanwhile, Lily thinks that she will win Neal's mother over by embracing his Indian heritage, but she takes it to a whole other level.

When Alex's childhood dog passes away, Whitney suggests they adopt a dog together. However, the adoption process isn't as easy as they'd hoped especially when dealing with pound owner Mrs. Janks. Meanwhile, Roxanne is interested in some financial advice and Lily, in an effort to bring them closer, suggests working with Neal, but things become increasingly awkward after a sexual mishap during their first meeting.