Racing with the Moon (1984) on Netflix

In the Christmas of 1942, in Point Muir, California, the seventeen years-old Henry "Hopper" Nash is the best friend of the reckless Nicky, who dates the local Sally Kaiser. Henry and Nicky have enlisted themselves in the U.S. Marines and they are waiting to be summoned to travel very soon. When Henry sees the gorgeous Caddie Winger, he has a crush on her and follows Caddie to find where she lives. He discovers that her address is a fancy manor on the top of the hill and Henry believes she is a wealthy teenager while she is actually the daughter of the maid. Sooner Caddie and Henry date each other and they fall in love with each other. Meanwhile Sally gets pregnant and Nicky needs a large amount for an abortion. They try to raise the money and when Nicky is desperate, he takes an attitude that will test his friendship with Henry.