Ray’s night with Kyla leaves him wondering who she really is; a competition develops at the Wellness Center; Tanya gets help from Charlie in finding out what happened to Ray’s money.

Ray and Tanya conspire to get rid of an explosive client. Charlie advises Tanya to keep Lydia happy. Lenore manages Sandee's rising demands, and Matt and Jessica bond.

The guest list for Frances and Mike's wedding doesn't include Tanya; Ray takes back what was his after a physical confrontation with Jason; Tanya finds a connection with Charlie's kids.

After Ray tells Lydia he's leaving the business, she takes Ray and Tanya on a ride they will never forget. Darby threatens to leave home, and Lenore confronts Jason about missing a date with a client.

Tanya discovers that Charlie has skipped bail, and she asks Missy, the mother of Charlie's child, to help locate him. Lenore declares war on Tanya and the Wellness Center, and Sandee tries to position Jason to take Ray's spot. Ray faces concerns about his ability to satisfy women, particularly Jessica.

Ray and Tanya must convince a bank officer and her friend that their "Wellness Center for Women" idea is financially sound. Lenore discovers a new prospect to rival Ray.

Ray worries that his cover might be blown when he confuses one of his former students with a client. Tanya finds her self taking care of a convicted felon, and Jess takes a job working the Dr. Matt Kopylov's office, the husband of Ronnie's mistress. Lenore makes a deal with Jason's fiancée, Sandee.

Ray's unscheduled appointment with Claire threatens his participation in a student-alumni baseball game; Frances has doubts about her affair with Mike and her business relationship with Tanya; Ronnie delivers a stern message to Ray.

Tanya takes matters into her own hands after Jason steals one of Ray's clients. Lenore discovers some surprising news about Jason. Meanwhile, Jessica tries living on her own, and Charlie asks Tanya for a favor. Ray works with a new client who likes to dress up as a cop.

Ray Drecker is a struggling high school coach in Detroit who is descending to all-time lows in his professional and personal life. He attends a self-help group in a desperate attempt to find a plan for financial success. Tanya, an old flame, is also attending the self-help group and she gives Ray inspiration in an unexpected way.

Tanya pitches Happiness Consultants to other women in her office, with mixed results. Damon goes to detention to hang out with his androgynous friend, leaving Ray baffled. Lenore gives Ray some lessons in branding and, after a chance encounter at a department store, offers Jessica some lifestyle advice.

Tanya enlists the help of a former colleague Lenore, who is now a professional shopper, so Ray can offer his services to her clientele of rich older women.

Ray's life continues to frustrate: His neighbor Koontz is on his case for urinating in the lake; he and Jessica continue to argue over the best way to parent the twins; and it turns out Lenore has disappeared, along with his wallet.

After standing him up, Jemma tells Ray they should take a break, and Ray seeks out Tanya for advice on women. Ray finds himself in an uncomfortable situation at Jessica and Ronnie's family barbeque.

Ray gives Lenore an ultimatum, and probes Tanya about the possibility of cutting ties with her fellow pimp. Disturbed that Damon has defiled the school baseball diamond, Ray considers Tanya's suggestion that his son find a new hobby to shake him out of his recent doldrums. Ignoring Ray's warning, Lenore offers Jessica advice in dealing with Ronnie. On his way to meet a new client, Ray has to think on his feet when he runs into Mike in a hotel lobby.

Tanya worries that Lenore may stage a coup for control of Ray, who is unnerved by rumors of layoffs at his school.

Tanya finally gets Francis to agree to dinner with Ray and Lenore is continuing to be a pest as usual. Ray can tell that Mike is struggling to not continue with his life and tells that he needs to look at himself and tell himself that he is wonderful. Damon goes back to the Poetry Bar and embarrasses Darby after which he has a performance "enhancing" scone and sees Jessica and Ronnie naked. Ray has to choose whether to cancel on the big client or his son who needs him.

Jessica turns to Ray for help with a rodent problem that may be imaginary. Rebuffed by Ray in her attempts to add Mike to her stable, Tanya gets guilt-management advice from Charlie (Lennie James), then goes to extremes to prove her success. Ray has difficulty thawing a client who is cold as ice.