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Sherri finds herself at a crossroads between re-kindling her relationship with Kevin and starting a new future with Randy. Celia and Angie have differing opinions about whom Sherri should choose. Meanwhile, Bart Peaslee tells Summer he's ready to officially begin their relationship, but first he'd like to spoil and pamper her with a head-to-toe make-over.

Sumner, Angie, and Celia are busy preparing meals for the less fortunate. However, they don't have a way to deliver the meals. One of the office colleagues decides to flirt with a cop to see if she can get the meals delivered. Soon the office colleague and the cop arrive at Sherri's house. Sherri's father is somewhat unhappy about having to share leftovers with so many people. Amid all the chaos Paula decides to tell both secret Sherri suddenly realizes that she has a lot to be thankful for.

Sherri hosts a game night so her friends can finally meet Randy. Celia brings her husband Miles, while Summer and Angie decide to each bring a date for the other. Thinking they'll be well-suited, Summer brings her plumber for Angie, but when Angie shows up empty handed, Summer decides to keep the plumber for herself. Randy seems to be charming Sherri's friends, until his answer to a hypothetical board game question leads Sherri to doubt his morals and his honesty.

After Bo tells her he hates her, Sherri volunteers to watch Julian, Paula's new baby. Sherri is suddenly summoned to the office to work on a weekend project and must take the baby with her. Sherri, Celia and Angie are not pleased when they learn Summer has brought them in to organize receipts for law partner Bart Peaslee's upcoming audit. Although Summer is ecstatic when Peaslee shows up at the office, she insists the ladies hide the baby.

Sherri and Celia are getting ready to play tennis when Paula goes into labor. Later at the hospital things get heated when there are problems with the baby. Meanwhile Celia, Angie, and Summer play board games.

Trouble begins to brew for Sherri when the topic of trick-or-treating as a family comes up. Sherri is upset when she keeps running into Kevin's pregnant girlfriend Paula everywhere she goes. Paula reveals that she has been trying to follow in Sherri's footsteps because Kevin says she's the best mother ever.

Sherri performs stand up about being newly single at a comedy club where her old friend Doug emcees. Doug is excited to hear that Sherri is single, reveals he's had a crush on her for years and asks her out on a date. Sherri decides to enjoy her newfound popularity and accepts. Celia and Angie have differing opinions on whether or not Sherri should let Dr. Gregg know she's going out with Doug. At dinner, Dr. Gregg corners Sherri and she admits she'd like to date other people.

Sherri doesn't want to date anymore after her date with Dr. Gregg goes bad. Redmond gives her the confidence to date again. Angie has trouble with Donna's daughter.

Celia invites Sherri to perform stand-up at a fundraiser she's organizing for her husband's church. When Sherri's routine is a hit and the church elders shower her with praise, Celia starts feeling jealous of the lack of attention on her as the First Lady of the church. Sherri's inflated ego causes Celia's competitive side to come out and she steals Sherri's thunder by singing beautifully on the church stage. Eventually, Celia apologizes for her actions but confesses that she feels like church is her place to shine. Meanwhile, Angie and Summer hatch a plan to get a discount membership at a high-end gym they've both been coveting by pretending to be a couple. via MyLifetime

Sherri struggles with Bo's first official custody weekend with Kevin, while her girlfriends try to show her the benefits of having time to herself. Angie drags Sherri to a bar, but a call from Bo cuts the night short. Celia takes Sherri to a meditation studio to help her relax, but it has the opposite effect, and Summer throws a party, but Sherri can't focus. She slips out of the party to spy on Kevin and Bo only to find the two nicely bonding. Sherri quietly slips away to do something for herself.

When Sherri can't reach Kevin by phone to confirm he's picking up a basketball hoop for Bo's birthday, she tries unsuccessfully, to sneak out of work and buy it. Already overwhelmed, Sherri is asked to take on Celia's workload when the president of the Minister's Wives comes to check up on her. To top it off, Sherri is locked out of the office without her purse during a company fire drill. Bo has a "zipper incident" at school which prompts Sherri to bring him in for another visit to Dr. Randy Gregg. Sherri finally buys the hoop only to discover Kevin already setting one up with Bo. via MyLifetime

Celia invites Sherri to perform stand-up at a fundraiser she's organizing for her husband's church. When Sherri's routine is a hit and the church elders shower her with praise, Celia starts feeling jealous of the lack of attention on her as the First Lady of the church. Sherri's inflated ego causes Celia's competitive side to come out and she steals Sherri's thunder by singing beautifully on the church stage. Eventually, Celia apologizes for her actions but confesses that she feels like church is her place to shine. Meanwhile, Angie and Summer hatch a plan to get a discount membership at a high-end gym they've both been coveting by pretending to be a couple. via MyLifetime

Single mother Sherri Robinson (Sherri Shepherd) juggles caring for her young son Bo and working part-time as a paralegal while pursuing her dream to become a full-time comedienne/actress. She splits from her husband Kevin (Malcolm-Jamal Warner) after she discovers his affair and finds solace and support from her girlfriends at the office. Kevin reveals that Paula, the 20-year-old he had an affair with and a fan of Sherri, is pregnant. On the bright side, Sherri's father points out that Bo's pediatrician, Dr. Randy Gregg, seems interested in her. Looking to blow off some steam, Sherri and her co-workers hit a local night club where things are not what they seem. via MyLifetime