Consider Breckenridge, Colorado. The Summit County resorts (Breckenridge, Keystone, Arapahoe Basin, Copper Mountain) are all great mountains and it's not as expensive to stay there as Vail. Breck has a decent bar scene and it attracts a lot of tourists during the high season, so if you're looking for drinking and girls you should be able to find some if you stay in Breck (at least more so than most places in UT or WY). It's right off I-70 and easy to get to from Denver International Airport which should be very easy to fly into from anywhere in the Midwest.
I grew up around there and I'm about your age so if you're headed out that way I can give you some more specifics.
I grew up around there and I'm about your age so if you're headed out that way I can give you some more specifics.