Rob Estes makes his first of two guest appearances in the first season playing Sam Towler, an old friend of Michael's who hits on Michael's wife, Jane. Estes would return as a series regular in the fifth season but in a different role playing Kyle McBride. He would remain on the series for three years until the series finale, where Kyle and Jane are a couple and expecting a baby. Jane was played by Josie Bissett, who was married to Estes in real-life for 13 years. They have two children together.