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, Clea, and Francine discover that Barry was enrolled previously in the military after his former Army commander, Major Curtis, recruits him for a secret mission. Denise loses the phone number of the man she met on the subway platform, but meets another man with the same name, causing her to consider dating him instead.

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.

Clea and Viviana help the agoraphobic Jamie meet his perfect match with a woman who accepts his anxiety disorder. After discovering Jamie is lying about his condition, Clean and Viviana threaten to tell Charlene the truth if he keeps being dishonest. Barry attempts to leave his girlfriend after discovering that she uses dating books to manipulate their relationship.

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.

Denise tutors Viviana, who must pass a college course to extend her student visa and avoid deportation. Viviana disagrees with Denise's strict teaching style, and asks Francine for help instead. After winning entry into the Tri-State tournament in Atlantic City, Barry turns to Clea for support.

Denise is faced with a major decision when her boyfriend Mike asks her to move in with him, however, when she finally agrees, matters get complicated.

Meanwhile, the Love, Inc. staff tries to help a man who wants his female friend, whom he is in love with, to see him as more than just a friend.