Samir, my favorite laid-back bar is ACE Bar
http://www.acebar.com. It's in the East Village. They have skee-ball, a jukebox and a mausoleum for vintage lunch boxes. I think a pint of Guinness is $6. It's a place where you go to socialize with your friends, not to be seen. Hence the reason why I've seen David Cross hiding out there.
Can't help on the clubs-front, but ACE Bar is close to the Lower East Side, where the stretch of clubs and s hit-shows are never ending. I could tell you places that are popular, but I can't vouch for their character.
Food-wise:
1) Breakfast at the Clinton Street Bakery is well worth the 1-2 hour wait if you go after 11:00 a.m. Also, a bagel at David's Bagel (19th street and 1st) is a must for the bagel connoisseur.
http://www.clintonstreetbaking.com/bakery-where.php2) Dinner is too tough a call without knowing if you're a vegetarian or what you consider expensive.
a) I personally get giddy over the cheeseburgers at the Shake Shack, as well as their cheap Brooklyn Ales, milkshakes and outdoor dining in a park setting. Don't be intimidated by the long line, it's actually quite efficient.
http://www.shakeshacknyc.com b) If I was going for taste and not atmosphere, I'd head over to Pearl Oyster Bar. An appetizer, wine and a lobster roll, will set you back $50-$60 a head. The guff you take from the waiters is worth it.
http://www.pearloysterbar.com/ c) For overall value
and taste, I'd go to
Lombardi's for some chianti and pizza! Again, a long wait depending on when you go, but well worth it. It's touristy. But there are somethings you just have to do, and pizza is one of them.
http://www.firstpizza.com/newyork.html
