A thirtysomething woman's life turns to chaos when an imaginary friend she created as a child returns after she begins dating a divorced father with three kids.

When Ben asks Alice to help him with her first mom-like task to pick up Bunny from dance class, Mary quickly discovers the simplest parental tasks are fraught with difficulty. Afterwards, Ben is disappointed when Alice tells him she can’t help with the kids anymore, but things change when Andy enlists Alice’s help to overcome his fear of taking a driving test.

Andy considers auditioning for the school musical, so Alice gets really involved and learns the emotional highs and lows of being a parent. Meanwhile, Dora creates her own feminist musical when she doesn't like the underlying message of Andy's show.

Andy has a hard time finding a prom date while Dora keeps turning down a guy who persistently asks her to go. Since Alice never went to prom, she convinces Dora to go so she does not miss out. Meanwhile, Ben struggles to deal with kids growing up, even trying to scare away Dora’s date.

Alice freaks out when her friends want to meet Ben. But when an outing with everyone goes surprisingly well, Alice wants to meet Ben’s friends. However, Ben is hesitant but devises a plan that will impress Alice; but later, he makes a surprising admission.

As Alice struggles to connect with Dora, she faces a dilemma of whether or not she should play the role of parent or friend. Mary is sure she has the right answer while Ben has his own agenda to have Alice be his personal mole. Meanwhile, Andy’s own unique identity is challenged when the one place where he feels cool is taken from him when Bunny tags along.

Ben’s divorce has been smooth sailing, but it hits rocky waters when his ex-wife, Renee, finally meets Alice. Renee doesn’t believe Alice is a good influence on Dora, Andy and Bunny, so Alice goes overboard to prove her wrong. Meanwhile, Andy and Dora fake being sick at school and devise a plan to get what they want and have their parents play off each other.

Ready to take their next steps as a couple and get engaged, Ben hides the ring in a pair of shoes that the kids donate to a charity drive, and the situation quickly gets complicated. Alice, not knowing the ring is lost, is concerned Ben has cold feet, and she takes matters into her own hands.