Guest Stars Nia Long as Tamara Mather Zickel as Michael Carlson Ronete Levenson as Tessa Taylor Gerard Hart as Alex Dushkin Evan Hart as Kyle Dushkin Co Starring Christine Nguyen as Hot Date #2 Debbie Jaffe as Ally Mercer Boffey as Monica's Date Aliza Pearl as Pepper Chris Rogers as Security Guy Erika Jordan as Hot Date #3 Tiffany Tynes as Hot Date #4 Halszka Kuza as Hot Date #5