There are three clothing optional places that gay men–of all ages–love to frequent: Rooster Rock, Sauvie Island (a sliver of Collins Beach) and bathhouses like Hawks or Steam, Portland's only gay bathhouse. Taking your clothes off is a great way to initiate a hookup. Queer dance parties are also comfortably co-ed, and it won't be weird if you bring your female roommate. Dancing is cool because you don't have to talk and somebody will make eyes at you at 1 am before walking right into your warm embrace. People in bars are awkward (everybody has phones now), and you probably don't smoke. For the main event, attend LGBT-themed dance parties like Blow Pony, S1 (if you recently graduated from college), a drag night at Lovecraft or Judy on Duty at the High Water Mark. If you want to get laid, utilize gay bars for pregaming. So, when you're 29, would you rather scroll your finger over that pic of them kneeling with a husky and cringe, or would you rather think 'I wonder if Mark wants to try that new fried chicken donut place tonight after the gym?' You can't go to Blow Pony alone.
Realistically, the guys whom you're excitedly chatting up because they're 'kinda cute' and 'so close' will still be there three years from now. Grindr is great for finding long-term relationships.