Not your grandmother’s Midnight Ma$$

I know you think your friends are funny and really great and all that. And sure, they are. They’re hilarious, screaming at each other over Rainier tall-boys and lying about how many Tinder girls have hit them up. Most nights, if you wander around the city for long enough and drink enough beer, you’ll be able to go home feeling like you’ve still got it after all these years.

But occasionally, your friends just aren’t going to cut it when it comes to meeting your crazy quota. It’s time to ditch the mundane. Hop down the rabbit hole that is Southeast Portland’s entertainment scene and get wild.

White Owl Social Club
1305 SE 8th Ave.
Now, we can’t just throw you into the fire. You’ve got to start slow on a night like this. And what better place to start than White Owl? Amazing food for carnivores and vegans alike, a side-eyed cocktail menu featuring local spirits, an impressive rotating tap list, and an irresistible photo booth where you can sit on your friend’s lap and show the world how spontaneous you are: you can’t go wrong here.

Order something hearty—I suggest the rice and bean bowl for herbivores and the bacon cheddar burger for meat-eaters. You’re going to need it to absorb the rosemary-infused liquor you’re about to drink.

And hey, White Owl also doubles as a music venue, so you may catch some live music now and again. After your second cocktail, go ahead and swagger (or stumble) your way to that photo booth.

927 SE Morrison St.
Obviously, after you’re done taking pictures of you and your boyfriend making fish faces, you’ve got to take it to the next level. Walk a couple blocks to Sassy’s and revel in the tacos and tatas. The only place worth sitting is the main stage, so buy yourself a drink, ask the bartender for some ones, and sit your ass at the rack.

The dancers here are pretty much like the dancers anywhere else, but so much hotter. Tattoos, librarian glasses, slinky American Apparel dresses, unexpeted music—everything from Beck to Band of Horses. It’s a Portlander’s wet dream, so sip your whiskey, and let your head start to spin.

Eventually, I’m sure, once all of your bills have disappeared from your hands—how the fuck did that happen so quickly?—you’ll get the urge to dance.

1001 SE Morrison St
Now that you’ve had some booties in your face, it’s time to shake your own. Conveniently, Sassy’s is directly across the street from Holocene, a music and art venue located inside a converted auto parts warehouse. Last time I was leaving Sassy’s, I narrowly avoided a random rave happening on top of a 15-passenger van. So that’s a thing.

On a given Saturday, you can plug into a myriad of events hosted by Holocene, including Booty Bassment, Verified and Gaycation. Tip: Sassy’s drinks are cheaper and their lines are way shorter, so knock one back before you go dance.

Midnight Ma$$ at Funhouse Lounge
2432 SE 11th Ave.
The clock is about to strike 12, but your night is far from over. Comedian Amy Miller hosts Midnight Ma$$, a monthly (vaguely) religious-themed stand-up showcase at Funhouse Lounge that runs from midnight to bar close. “Comedy fanatics often hear tales trickling out of New York or LA about Chappelle dropping into an open mic or Louie doing a spot on a basement show,” Miller said.

“Many Portlanders don’t realize that all it takes to experience some of this big city magic is to be a night owl!” Miller said the show has seen the likes of Dave Attell, Norm MacDonald, Kurt Braunohler and many many more. When celebrities don’t show up, the audience still gets a free taste of some of the best standup from Portland and beyond. Even the crabbiest of morning people manages to stay awake for the jokes and Miller’s energetic hosting style. Follow @midnightmassPDX for updates on upcoming shows.

Fair warning: If you have a crippling fear of clowns, steer clear of Funhouse’s nightmarish Clown Room.