After some encouragement from his therapist, Jason attends his friend Erick's wedding with good intentions, but the event is filled with pressure from family and friends for him to finally settle down. Erick deals with a bout of cold feet and marries Lisa. Things take a turn when a love from his past arrives at the reception.

Jason gets a new assignment at work with a well-known client. Lacy gets the call for an audition that could put her acting career back on track. After a run-in with her ex-husband, Lacy's attitude and inability to let go of the past affects her future prospects. Jason unexpectedly goes to a speed dating event and runs into Erick's ex, who invites him to a party with ulterior motives.

Erick's father makes a surprise weekend visit with the hopes of getting to know Lisa better. Patricia urges Jason and Alexandria to settle down. Jason reluctantly rolls solo to his married friends' get-together and the event quickly goes downhill.

Jason finally meets his new client, Lola Lane, and deals with the work place blues. Lacy goes out with the date she's been hiding, Steven, and runs into Bryan who learns why she's been hiding him. Alicia is tired of waiting for Bryan to be ready to get married, and the two discuss the future of their relationship.

Jason and Cody celebrate their new business along with the rest of the gang, who each have exciting news of their own, but there are many surprises that will follow them along the way. Jason gets news that could change his life in more ways than one.