Nick Watt doesn't quite understand Portland, Oregon. In the last decade the population has risen over 50%, much of which is accounted for by young people-musicians, artists, and the otherwise alternative-but Nick wants to know why they come to Portland and not another city. Is there some great draw that he's just too old and un-hip to understand or is it something deeper than that? Nick arrives in Portland unsure that he'll fit in-he's clean shaven, doesn't have any piercings, and despite having worn a necklace for a brief time in his youth, dresses like a Midwestern accountant-but that's not going to stop him from trying. His first stop is the Alberta Rose Theatre, where members of the Wanderlust Circus are practicing their musical and acrobatic acts. He meets the director Noah Milkens, who tells Nick how he ended up in Portland. In any other city "avant garde circus performer" might not be a viable career choice, but Noah found kindred spirits in both his fellow circus geeks and an audience that would appreciate their art. Noah is aware of the "Portlandia" stereotype that exists in the rest of the country, but tells Nick that it doesn't concern him at all-one thing that sets Portland apart is that you can be as weird as you want as long as you are yourself. After begrudgingly participating in one acrobatic trick with the Wanderlust Circus, Nick meets Thomas Lauderdale, the eccentric lead singer of the indie band "Pink Martini." Thomas gives Nick the grand tour of his loft and helps him understand the creative culture in Portland. They decide to hit the town in Thomas' car, a vintage Nash Metropolitan, but first they need to get it started. After a push from behind and a near miss with a trolley-car they're on their way. Sort of. The Metropolitan stalls again, so Nick and Thomas decide to abandon their wheels and walk the rest of the way to Darcelle XV, one of the oldest drag clubs in America. Nick meets Darcelle-real name: Walter Cole- as he's getting ready for the night's performance. The octogenarian drag queen tells Nick about his former life as a blue-collar family man and how the city itself helped him be true to himself. The next morning Nick has an appointment with Samantha Hess, perhaps the only "professional cuddler" in the world. He arrives early to find her door unlocked with signs leading him to her bedroom- nothing sexual, Samantha just isn't home yet. Samantha finally arrives and Nick observes as she cuddles up to her latest client Gretchen, an emergency room nurse who seeks Sam's help to relieve stress. Nick decides he has to try it for himself. Sam explains to Nick that Portland inspired her business; the city shows the same unconditional love and acceptance to its citizens as she does to her clients. As Nick drives around the city he notices something, Portland is very white. It's actually the whitest city in America, 75% white. Something else he notices, it's home to abnormally high number of strip-clubs. Nick drives out to a quiet residential neighborhood to meet Liv Olthus-AKA "Viva Las Vegas"-an author and musician who also happens to be a stripper. Nick goes with Liv to Mary's Club, a gentleman's club owned and operated by women. Thomas Lauderdale joins Nick in the front row and invites him to a sing-along cocktail party at his loft later that night. Nick Watt doesn't sing-it's his idea of hell-but the last few days have rubbed off on him and he gets into the spirit of the party. He meets the former Mayor and a number of other famous personalities in the Portland social scene, and he finally starts to understand the Rose City's credo: "Keep Portland Weird." It's not about being weird for the sake of it; it's about being brave enough to be who you really are and accepting others who do the same.