Sara and Sophia are working on some computer data entry for Regina when the computer crashes. Bullethead will fix the problem on one condition - Sara must go on a date with him. Reluctantly, Sara agrees and when Bullethead repairs the problem she is grateful.
With Steve's old friend and singing sensation Brian McKnight in town, Cedric visits Steve to find out if he was able to hook him up with tickets to the show. As promised, Steve delivers Cedric a set of nosebleed seats. Steve's seats are front row center. Despite Cedric's taunts, Steve asks Regina to be his date for the concert. Regina has a policy of not dating co-workers, but considering she can't get tickets on her own, she breaks her rule just this once and agrees to go. However, their plans are disrupted when, having recently left her wealthy husband, a former girlfriend, Alise, arrives to make amends with Steve. She showers Steve with expensive gifts and he can't getting re-involved with her.
Sara is unhappy about her date with Bullethead but doesn't know how to let him down easy. Sophia suggests she lie to him. Sara begins telling Bullethead a lie, but is surprised when he asks her about her perfect date. Sara suggests a moonlit walk on the beach and picnic under the stars.
Alise shows up at school to and meets Regina. Alise is rude and obnoxious to Regina. Steve is concerned he offended Regina and heads off to apologize to her. Convinced Alise and Steve are an item, Regina returns the shredded concert tickets and calls off their date. She also suggests their relationship remain only professional. Despite Cedric's cautionary words, Steve decides to pursue a relationship with Alise. When Alise soon suggests living together and kicking out Cedric, Steve explains he likes his life as is, including living with Cedric. So, admitting there's little to their rekindled romance beyond the sex, he reluctantly returns Alise's lavish gifts and sends her on her way.
Sara is touched and second has thoughts about dumping Bullethead when he goes out of his way to create the perfect date. He builds a seaside scene and even brings sand to their date.
In an effort to win Regina's trust and respect, Steve enlists the help of Brian McKnight, who visits Regina and sings to her.