The gang all learns that Mike (played by Bianca Kajlich's real-life husband Mike Catherwood) is going to propose to Leslie. Danny is tasked with keeping Leslie distracted, only to hear his sister say she thinks Mike is way more serious about their relationship than she is. Danny then leaks the secret about the ring, making Leslie angry.

Jackie (Christa Miller), the older woman to whom Danny lost his virginity when he was 17, is returning to town. While Danny assures his friends that Jackie can no longer control him like she did when he was younger, it quickly becomes clear that she can still get him to do whatever she wants.