What is the name of this movie about boy loses virginity [closed]

Question

Okay so it's been like 15 years since I saw half of this movie, always wanted to see the whole thing. I can remember a few tidbits.

1: The main character is a 20 something kind of nerdy boy. There is a scene where he is losing his virginity with a pretty girl. He's kissing her constantly and she says something like 'You don't have to keep kissing me the whole time, you can just look into my eyes'

2: The main character narrates a voiceover where he says he finally understands why people are so obsessed with sex. Something about, when you are doing it... you and seeing how much the girl is enjoying it, you feel like you're the best in the world

3: Another scene he decides the best way to live is to become 'all things to all people' He decides (I think) to impress his dad by being an ambitious business type guy, and make his hippie mom happy by smoking weed and listening to records. (pretty sure his parents were divorced)

That's all I can really remember, it was a slice of life philosophical kind of movie heavily narrated by the main character. I've tried searching quotes and stuff about the scenes I remembered once in a while over the years but could never find it.

Answer 1

100 Girls (2000)

This sexy, teen-comedy is about a freshman, Matthew, at college who meets his dream girl in a dorm elevator during a blackout. He never sees her face, but instantly falls in love. In the morning, the power is restored, but the "dream girl" has vanished. All Matthew knows is that she lives in an all-girls dorm. He sets out on a semester-long journey to find his mystery girl amongst a hundred female suspects. Could it be Wendy? Dora? Arlene? Patty? Cynthia? Or the 95 other girls, any of whom could have been in that elevator with Matthew.

Here's the first scene you describe:

The specific dialog begins at 1:28:

Hey, you don't have to kiss me the whole time, seems like you're kissing me just to avoid looking at me. Look into my eyes.