To be honest, some parts of the game just seem silly. For example at one point of the game, you can save someone from killing themselves. If you pick "confident" as your mood, you'll get a message back saying "UR 2 CONFIADANT! UR FREND DIESSSS!".
Your choices over the game change your stats, and your stats actually change the outcome. This is especially important for the "Keep going or stop" trials you can do in high school. The game also tricks you into thinking that the next time you play, you'll know the correct choice (especially evident in the pimple scene - everybody knows that you don't pop a pimple slowly right before a dance!). I played the game through 10 or 20 times as both genders when I was younger. I'd usually save the jumper 70% of the time, but if you don't pick the mood that matches your displayed personality best, you pay for it. I remember the first time I lost him, I picked confident, but I was such a wuss that my false bravado got him killed. Another time, I went to get help, but just couldn't find anybody.
I also lost my first game to baseball. If you're physically fit, you will actually win the baseball game.
In the DOS version, there was a bug (specific to playing on Windows, I think) where you couldn't pass enough time to actually finish the teenage phase. You would run out of school, work, and general experiences. To get through, I had to try to propose to my girlfriend over and over and get the "her parents don't think you're old enough" message, which advances your age by 2 weeks.