relents after Jim expresses disbelief). Recurring Kyle, portrayed by Billy Aaron Brown, is Bridget's – and later Kerry's – boyfriend. He is often seen spending time with Rory when not with either Kerry or Bridget. His father, Tommy, used to work with Paul. Ed Gibb, portrayed by Adam Arkin, is the principal of the local high school. He and Cate knew each other in high school, and even dated. Their accounts of their first romantic encounter are different, each professing to have had more self-control. Despite this, they have some very intimate moments. Coach Scott, portrayed by Dan Cortese, is a high-school coach on whom Bridget had a crush. He likes Cate, and Cate initially likes him, but then discovers Bridget's crush, which causes her to deny Scott's romantic advances towards her. Jenna Sharpe, portrayed by Nikki Danielle Moore (2003–2005), is the daughter of Paul's boss Nick, and one of Bridget's rivals, who later becomes her friend. She has a younger sister, Rachael (Nicole Mansour), who is a friend of Kerry. Missy Kleinfeld, portrayed by Daniella Monet (2003–2004), is Rory's love interest in Season 2. She has a sister, Sissy (Elena Lyons), who likes C.J. Jeremy, portrayed by Jonathan Taylor Thomas (2004), is Bridget's tutor and eventual boyfriend. He is considered a nerd at school, and because of this, Bridget at first denies her interest in him. Anthony W., portrayed by Cole Williams (2002–2003), is a student in Bridget's class. He is a white boy who speaks like a black rapper, often resulting in confusion. In "Cool Parent", he is shown to play lacrosse. Maggie Barnes (née Egan), portrayed by Cybill Shepherd, is Cate's sister and C.J.'s mother. Maggie shares the same sensitive, moody nature as Kerry. However, it appears (from a conversation between Ed Gibb and Cate) that Cate was the smarter one, as well as being more popular. Fred Doyle, portrayed by John Ratzenberger, is a persistent and overly friendly neighbor of the Hennessys, and husband of Mary Ellen (portrayed originally by Shelley Long and then by Cindy Williams). He is the father of Donald "Donny" Doyle, who has dated Bridget for some time. Fred is the head of the neighborhood watch, and his family is religious. Mrs. Crupp, portrayed by Suzy Nakamura, is a math teacher at the school. Damian, portrayed by Paul Wesley, is Bridget's ex-boyfriend who appears in two episodes. Lacey/Lacy, portrayed by Kala Savage