But all the places you mentioned are at least 1.5 hours drive from San Jose. You can't expect me to drive 1.5 hours just to not have to sit at home every time I want to have some fun? I love day trips, but I don't want to have to to a day trip every weekend or every day I want to have some fun. Compare that to LA or San Diego where you don't have to drive far to have fun (nightlife for example) or awesome beaches. All I see in San Jose is empty streets after 9pm. There is nothing going on in this town besides work.
But here's one thing I've found: People who really want to have fun find a way. There are small pockets all over the bay. SJ downtown is a little lame but it is getting better
We do have hiking trails in the area too, particularly up in the Santa Cruz Mountains, and Henry Coe State Park is a little less than an hour away. There are a number of wineries in Los Gatos and Saratoga, around half an hour away. I'm less familiar with the microbrew scene around here, but I know there's mead in Sunnyvale (~30m) and a handful of larger "micros" like Rock Bottom in Campbell and Lazy Dog in Cupertino. NHL is downtown, NFL is ~30 min away in Santa Clara, etc.
You're overstating the issue. It's not New York or San Francisco, for sure, and we sure do need better rapid transit but you're definitely not an hour and a half from everything cool. You're more like half an hour or so. You just need to look for it.
Sounds like you're simply living in the wrong place. Within 30 minutes, I can drive from SJ to a number of great hiking trails or take my road bike to some super fun hills. Of course the streets are empty after 9pm... people want to be able to get outside when the sun is up!