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Main Plot:Denise aids an old boyfriend in finding a new love and Clea confesses some not so good news about her love life.
Clea struggles with her emotions as she and her soon-to-be ex-husband work out the details of selling their apartment.
After a chance run-in with a great looking stranger on the subway, Denise habitually returns to the location where they met in hopes of finding him again. The Love, Inc. staff has a difficult time finding a mate for Renee, a hard-to-please client who has an outrageous list of qualities that her perfect mate must have.
Denise's new boyfriend Grey invites her to his birthday party for their second date. At the party, she becomes increasingly confused and paranoid as he keeps disappearing throughout the night. Clea assigns Viviana to arrange a date for the agency's first lesbian client.
While working with an older, white man under the delusion that he is hip, Francine discovers that he is more interested in dating her than finding a potential match. Denise grows attracted to a veterinarian and lies to him about her dislike for animals to make herself more appealing to him.
Clea feels conflicted about her date with Father John, a former priest from her church who renounced his vows to search for love. When the date becomes more intimate, Clea becomes hesitant about the future of their relationship. Denise and Barry help a man acclimate to his life after prison by encouraging him to search for his possible soulmate.
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.
Clea convinces Denise to spend Thanksgiving with her to avoid feeling lonely. Clea becomes increasingly attached to Denise over the course of the day. Francine and Barry encourage a client to propose to his partner.
Viviana accepts a marriage proposal from a younger man, but feels conflicted when her ex-boyfriend returns to rekindle their relationship. The agency begins to market its services towards geeks, and Barry and Francine experience difficulty arranging dates for a trio of clients.
Francine is confronted by her mother over her friendship with her biological father who abandoned her a child. Denise and Barry help a 12-year-old child arrange a date with his crush.
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.
Denise recruits Francine to change her new boyfriend Mike into a perfect partner. Clea and Viviana use Barry as a fake date to get revenge on a difficult client who has an offensive sense of humor.
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.
A jealous Francine confronts Denise for spending all of her free time with Mike instead of her. Barry and Vivana attempt to help Eric, a fireman with hero syndrome.
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.
