Kelly learns that she is pregnant, and has difficulty breaking the news to her mother. Brandon is thrilled, but Kelly isn't sure that she wants the baby. Driscoll suggests that Valerie sell her shares in the club so that she has more money available for investment. Val makes a pass at David, prompting Donna to order him to end their working relationship. Valerie eagerly accepts David's buy-out offer. Clare is saddened by Mother's Day, so Steve tries to take her mind off things by going for a drive. Clare believes that her father cannot handle discussion of her mother, but Steve discovers that he was trying to spare Clare's feelings. He brings them together to reminisce.

Music: ""Don't Take It Personal (Just One of Dem Days)"" (#2, 1995) and ""For You I Will"" (#4, 1997), performed by Monica

Kelly and Matt babysit Erin, and have sex in the living room after she goes to sleep. They do not realize that Mel and Jackie have set up a video camera to observe prospective nannies with Erin. Erin switches the tape with a copy of ""There's Something About Mary,"" and the illicit video ends up in Dylan and Gina's hands. Dylan becomes furious, prompting Gina to suspect that he still has feelings for Kelly. She believes that Dylan is trying to overcompensate by arranging a private concert by Monica, and tricks him into admitting that he slept with Kelly in Mexico. Matt breaks up with Kelly, who reminds him that he was married at the time. He forgives her after she insists that she never revealed the truth because she did not want to add to his woes. Donna asks Wayne, a good-looking pro beach volleyball player, to model her new line of men's wear.