Yes, Dear (2000)

S5E4 High School Reunion

During the gang's high school reunion, Greg finds himself unwittingly pretending to be a popular student after being mistaken for one of them. This situation ignites jealousy in Jimmy, who feels his title of "Coolest Guy" is at risk. Meanwhile, Kim hatches a plan to rekindle the interest of her former high school stalker. Additionally, an inappropriate and aging teacher continues to pursue Christine, adding an awkward twist to the reunion festivities.