When Whitney and Alex, a happily unmarried couple, attend one of their friends' weddings, Whitney realizes that she and Alex are dangerously close to relationship boredom after three years together. Determined not to let that happen, Whitney consults her close circle of opinionated girlfriends Lily and Roxanne. Snapping into action she tries to seduce Alex in a sexy costume, but someone winds up in the emergency room.

Whitney re-creates the first date she and Alex never had.

Whitney and Alex have a movie night at home, but the evening soon becomes a competition over who is most romantic. Meanwhile, an edgy Lily anticipates Neal's imminent proposal, sparking Mark's mission to prove that women are more eager to marry than men.

Alex becomes angry when Whitney takes a friendly competition at Low Bar too far; Mark learns that R.J. has a fear of spiders.

Whitney catches Alex checking out an attractive woman but he refuses to admit to it; Roxanne tries to make her ex-husband jealous.

Alex lies to Whitney about going away for a tech seminar in order to have some time by himself; R.J.'s niece becomes friendly with Roxanne.

Alex lets his ex-fiancee crash on the couch without consulting Whitney first; Lily has a date at Roxanne's apartment.

Whitney is not enthused when Alex tries to bring his former motorcycle days back to life; Lily orders new beer for the bar without Mark's approval.

When Alex and Whitney decide to take their honeymoon at his family's lake house, they find his father there; Mark, Lily and Roxanne hang out at Whitney and Alex's apartment.

When Whitney (Whitney Cummings) and Alex (Chris D'Elia) go on a double date with Roxanne (Rhea Seehorn), 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 (Zoe Lister-Jones) thinks that she will win Neal's (Maulik Pancholy) 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.

When Lily asks Whitney to be her maid of honor and plan her engagement party, the stress drives Whitney to see a therapist; Roxanne decides to take control of her future.

After a revelation from Chris, Whitney decides it's time to come clean about past falsehoods; Mark hires a new bartender.

When Alex (Chris D'Elia) encourages Mark (Dan O'Brien) 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 (Whitney Cummings) steps in for guy's night out, only to run into Mark and his new best friend, Neal (Maulik Pancholy). In an effort to reunite the bro-mance, Whitney, following advice from Lily (Zoe Lister-Jones) and Roxanne (Rhea Seehorn), arms herself with some Rocky Road and red wine and sets out to discover the real root of Mark's heartbreak.

Whitney and Alex scheme a way to skip out on their family gatherings to start new holiday traditions with their friends Lily, Neal, Mark and Roxanne. However, Whitney's little white lie to her mother Candi and an unexpected visit from her father, Vince, cause her perfect plan of merriment to unravel.

Whitney's reaction is less than heartwarming when Alex falls off a stage while speaking at his alma mater; R.J. tries to teach Mark about chivalry.

A terrible ex-boyfriend contacts Whitney in hope of making amends; R.J. presents a theory to Roxanne.

Whitney thinks her father has changed for the better when he visits and gives her $5,000; while Alex thinks Whitney should rent an art gallery and display her photos, Whitney gives the money to Lily, who is very short on cash.

Whitney asks Alex to spend time with Lily; Mark and R.J. start a competitive game of darts to bring some excitement to Low Bar.

After an argument over whether or not Alex uses a condescending "tone," Whitney decides she is going to catch her boyfriend in the act and enlists Mark's help. The two scheme to set up a hidden camera in the couple's apartment. Lily, Roxanne and Neal gather around the television to watch the drama unfold. Later, Alex's brother Brian crashes on the couch, and old sibling rivalries come to the surface causing the two brothers to brawl.

Whitney and Alex head to City Hall to get married, but Whitney's driver's license is expired and sparks an unusual chain of events that interferes with their wedding plan. Whitney's father tries to come to the rescue. Mark confesses his feelings for Roxanne to Neal and Lily.

Whitney's mother interrupts the celebratory mood of Whitney and Alex's unofficial wedding day; Lily and Roxanne have trouble choosing a gift for Whitney.

Whitney's half-sister visits to discuss a life-altering decision; Alex and Mark try to cheer a depressed R.J.

When Alex becomes jealous of one of Whitney's co-workers, the two decide to try couples therapy; Mark and Roxanne realize they make good partners while at Lily and Neal's game night.

While trying to figure out what is making Alex's allergies act up, Whitney reveals she has a heart condition; Lily introduces her new boyfriend to her friends.