Alice falls in love with a divorced dad but she then learns that he has 3 kids. Alice becomes consumed by her fears and contemplates giving up until her old childhood imaginary friend, Mary, comes back.

Ben asks Alice to help him with her first mom-like task: picking up Bunny from dance class, causing Mary to discovers the simplest parental tasks are fraught with difficulty. Later: Ben is disappointed to learn Alice 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 away a guy who persistently asks her, but Alice tries to convince her to go. Meanwhile, Ben struggles to deal with kids growing up and tries to scare away Dora's date.

Alice wants to meet Ben's friends, but Ben is hesitant. Later: he makes a startling admission after devising a plan to impress her.

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.

When the kids donate the shoes Ben hid the engagement ring in to a charity drive, Alice worries the delay in his proposal is due to his cold feet.

Alice is ready to sleep over at Ben's when his kids are in the house, but Ben worries the nightly rituals will put her off; when Alice gets rattled, she gets Mary's help in an attempt to fix the situation.