You got a designated, right? Or taxis? Or a sturdy pair of limbs?
I think a little bar hopping is in order.
If you want to have a well-crafted cocktail, and be adult about it you can start at Teardrop Lounge in the Pearl. If you want to
begin well, this joint is in the upper echelons for the whole west coast. Don't be afraid to ask questions, the cocktail list is very sophisticated. Clyde Common on downtown Stark Street is a restaurant with another upscale bar; the head bartender there is named Jefferey Morganthaler, google him if you want to be geeky about it. (You can also feign inebriation from this point to branch out to some other nearby liquor holes, wink wink.)
My third upper end joint just opened, Beaker and Flask. It's on the other side of the river on around 8th. You'll have good bar snacks here, too. I haven't had the chance to try it yet, but the word is good.
But being young you may not be interested in upscale. Or lower budget, I certainly was at 21.
So then, Crush is a great joint. It's gay, but the sort of gay that's like neighborhood-come-one-come-all gay, not helicoptering cocks gay. I think straight people even go there.

On like 14th and Belmont, I want to say. Too bad there aren't more places like this around.
If you want to fertilize your white sunglasses side, my friend you are in the right town. Throw a stone. Pick a neighborhood. The Florida Room? The Know? The Nest? Crow Bar? That lame milk bar on Mississippi? C-Bar? Bar of the Gods? The Maiden? Plan B? God, there's a million of these sorts. You have lots of options at this level. What's the target neighborhood?