A less successful movie I liked a lot was Milk Money


About an 11-or-so kid who lives with his widower father(Ed Harris), and he and his two 11-year-old classmates have this idea to pool their piggy-bank money, go downtown and hire a hooker (Melanie Griffith) to let them see her naked. The situation evolves into them bringing her to their classroom for show and tell so they can do a fun presentation on biological reproduction for the class. That scene alone is really funny.
Then as things progress the kid grows to like her and think of her as a possible wife for his dad, and a mom for him.
The whole hooker-with-a-heart-of-gold thing.

Not a box office hit or critically acclaimed, but both me and my girlfriend really enjoyed it. So it withstood the date test.