Jeri Ryan As Sherri Now
Jeri Ryan is best known for her role on Star Trek: Voyager, where she played Seven of Nine. She also starred in Leverage, Body of Proof, and Major Crimes. She is married to Christophe Eme, and the two have two children together.
Kimberly Williams-Paisley As Gretchen Martin Then
Kimberly Williams-Paisley portrayed Gretchen Martin, Larry’s sister in the eleventh season of the show. When Alan begins to dat her, he tells her that he owns the apartment and he doesn’t live with his brother. Eventually she figures out that he is lying to her and they break up.