Hillary is always struggling in life and love while constantly feeling the pressure to marry from her demanding mother. This holiday season, she thinks she finally has it right but when Hillary's fiance suddenly breaks up with her, she scrambles to find a fake fiance. After posting an ad online, she hires David, an out-of-work actor to pose as her fiance in front of her mom, her dad and her snobbish sister Trish. Her fake engagement starts to unravel...

Lizzie and her graduating eighth grade class take a trip to Rome where she is mistaken for an Italian pop star.