Denise helps a former flame find some new love, while Clea comes clean about her less-than-stellar love life.
Denise and Francine try to help Clea break it off with ex-husband Daniel, but they soon are torn on how to handle the situation when they see Daniel's fiancé having an affair. Meanwhile, Barry wishes he could get romantic with his new client.
Denise starts frequenting the subway train line on which she met a handsome guy, hoping he’ll turn up again. Meanwhile, the staff is saddled with the task of finding a match for a woman whose desired qualities in a mate are far too unrealistic.
On their second date, Greg invites Denise to his birthday party, but his frequent absences during the night lead her to believe that maybe he's not romantically interested in her. Meanwhile, Clea puts Viviana to work finding a match for a gay woman.
Francine tries to help an older white man with delusions of cool find a match, only he really wants to get to know her instead. Meanwhile, Denise pretends to be comfortable around animals in order to get close to a hunky veterinarian.
Clea hesitantly accepts a date from her church’s former priest, Father John, when he explains to her that he is no longer a priest because he wants to fall in love, but finds herself unable to see past the collar. Meanwhile, Denise and Barry try to help a recent ex-convict get back into the dating scene.
The Love, Inc. crew tries to help Clea be more spontaneous after she tells them her ex-husband felt she was too restrained. Meanwhile, Denise and Barry assist a man too nervous to go out on a second date with a woman with whom he had a successful first date.
Denise begins to think that her relationship with an old friend was more as an advisor than a friend, when the friend, once overweight, but now svelte, comes into town with an independent and more self-confident spirit. Meanwhile, Clea's insecurities come into play when she discovers that her new flame, David, has a sexy roommate.
As Clea s relationship with David (Rick Fox) moves forward, she is distressed to learn that his roommate is a beautiful model.
Clea tires of losing to her overly-competitive boyfriend, David, so she tries to find the one thing in which she can prevail over him. Meanwhile, Denise and Barry try to find a woman, whose job as a subway token clerk keeps her inside a bulletproof booth.
Clea coaxes Denise into spending Thanksgiving with her so that she won't have to think about her recent divorce, but Denise quickly finds Clea smothering her a bit too much.
Viviana accepts a marriage proposal from a young man, Charlie, who is okay with her using the marriage to get a green card, only to find that her former love has come from home to restart things with her. Meanwhile, Barry and Francine try to set up three dorks with dates.
Francine is saddled with her visiting, controlling mother. Meanwhile, Barry and Denise try to help a boy looking to woo what could be his first real girlfriend.
Barry's old superior from the Army comes to recruit him for a matchmaking assignment, namely himself, which reveals to the group Barry's former military status. Meanwhile, Denise tries dating another Mike Smith after thinking about the one that got away on the subway.
Clea throws a Valentine's Day party for all the dateless clients who are alone on Valentine's Day, but the partygoers react angrily when they find out the event has been less-than-flatteringly dubbed by the staff to reflect their "loser" status. Meanwhile, Clea finds herself agreeing to date a stranger named Larry after David tells her he can't get home in time for a romantic day with her.
Major Curtis tries to get a quality date for his daughter, Molly, but when the staff finds out that she is already in a relationship with an older man, they must try and get the couple to split. Meanwhile, Clea forces herself to be honest with David about her unexpected kiss with Larry.
A timid Denise enlists Francine to take on the chore of convincing her new boyfriend, Mike, to change himself. Meanwhile, Barry is brought in to serve as a ringer date for a client who has an obnoxious funny bone.
The staff tries to get one of their clients to come clean about his faked agoraphobia, which he played up for his date. Meanwhile, Barry has trouble getting out of a relationship with his manipulative girlfriend.
Clea engages a series of different soul-searching processes to figure out what the cosmos has in store for her relationship with David. Meanwhile, Francine is turned off to the fact that her sensitive date’s tear ducts are always turned on.
Francine begins to feel like an outsider in Denise's life now that she's got her boyfriend, Mike. Meanwhile, Barry and Viviana attempt to find a match for a firefighter who always feels the need to move on after playing hero to his dates.
Denise offers some assistance to Viviana with a class she needs to pass for the sake of her visa, but Viviana turns to Francine for help instead when she starts to feel like Denise's tutoring methods are too tough.
Barry wins a poker tournament and decides to use his money to help one of the staffers achieve a long-term goal, but the generous act causes everyone to compete for the money. Meanwhile, Clea shows a client how to understand when a man is sending her romantic signals.
Denise finds that things get more complex than she anticipated when she agrees to move in with her boyfriend. Meanwhile, the staff tries to help a man woo a female friend who doesn't know he wants to escalate their relationship.
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