Clea reveals to the staff of Love, Inc. that her ex-husband frequently criticized her for not being spontaneous enough. The staff attempts to make Clea less serious. Denise and Barry try to encourage a client to overcome his anxiety and go on a second date with a woman he cares about deeply.

Denise reunites with her former college friend, who had recently lost a dramatic amount of weight, and rejects all of Denise's advice and concerns. As Clea feels more attracted to her boyfriend David, she becomes paranoid after finding out he has a female roommate.

After discovering that David has a highly competitive personality, Clea attempts to find something at which she can beat him. Denise and Barry help a client to connect with a woman who works behind a bulletproof window at a subway station.

Denise, Francine, and Barry are angry at their clients' demands for the perfect Valentine's Day dates. Clea plans a party for her employees and clients to appease them. The clients riot after overhearing the staff call the party "The Losers' Ball". Clea feels neglected by David, causing her to agree to go on a date with Larry.

Major Curtis recruits the agency to find a suitable match for his daughter Molly. They discover Molly is secretly dating a much older man and attempt to break up that relationship. Clea struggles with whether or not she should tell David about kissing Larry.

Confused about her relationship with David, Clea seeks advice from Viviana's psychic, Denise's therapist, and Barry. Francine is turned off when she finds out that her date cries too much.