Guest Stars Nia Long as Tamara Mather Zickel as Michael Carlson Taylor Gerard Hart as Alex Dushkin Ronete Levenson as Tessa Evan Hart as Kyle Dushkin Co Starring Christine Nguyen as Hot Date #2 Halszka Kuza as Hot Date #5 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