I haven't seen this one but encountered the description while researching movies:
Eight Days a Week (1997) starring Joshua Schaefer, Keri Russell, R.D. Robb, Catherine Hicks / From IMDb: Peter loves his next-door neighbor, Erica. On the advice of his grandfather, he decides to camp out on her front lawn for the entire summer or until she agrees to go out with him. His father is none too happy about the idea and refuses to let his son back in the house, even to get a change of clothes. Peter's friend, Matt, thinks Peter should give up on women (as he has) and just have sex with fruit.