Living with Fran (2005)

Riley and Fran realize they don't have many common friends because of their generation gap, but find her friend Becca and his Danny ideal for a double date on their anniversary. When the girls overhear Riley saying he pretended the cool leather coat she gave him is too delicate for him to wear in construction, she's livid but decides to test him further by giving instead an indestructible watch. Meanwhile Josh has fixed his nasty sister Allison a date with hunky Cory, but she and her cahoot dump the lovely boy just because he's a freshman, hence 'social suicide for sophomores'.