The Portland That Wasn’t: With Missed Connections, it’s flirtation without consequences—or closure

With Craigslist’s Missed Connections, locals flirt without consequences—or closure.

Willamette Week | Feb. 9, 2011

If Mike Gutowski had said hello to the cute girl in the peacoat and Converse All-Star sneakers who boarded the No. 6 bus after him on a Friday evening, this would be a different story. He and the girl made eye contact and exchanged smiles as they traveled south along Martin Luther King Jr. Boulevard. But rather than start an across-aisle conversation that might make him late to his friend’s house, Gutowski got off the bus silently at his stop and posted this ad on Craigslist’s Missed Connections page the following day:

6 MLK bus exchanging glances – m4w

To the extremely cute girl on the MLK 6 yesterday 7:30-ish… Loved the smile : ) You wore a longer brown coat and a pair of low-cut caramel-colored Chuck Taylors…

He hasn’t heard from her.

“Does she even know about Missed Connections?” asks the tall, dark 34-year-old tattoo artist. “I didn’t even know about it until a year ago.”

Since Craigslist established a Missed Connections page in the Personals section of its Portland site in the fall of 2002, the number of posts has multiplied from fewer than five to sometimes 100 per day.

Against the stark white website background, blue letters recall encounters at bars, coffee shops, grocery stores, elevators, gyms and stoplights during rush hour. They describe outfits and distinguishing features, mention glances, smiles and blushes, declare love and lust — and vent anger, frustration and broken hearts. “Sunday jogger guy,” “Redhead at Kinko’s,” and “On the max with your prego sister,” they say. “You blew me kisses as my bus pulled away” and “What you must feel like (fuck you who cares).”

The entries offer a glimpse into the Portland that would exist if people didn’t face obstacles or inconveniences and acted on all their impulses. They hint at what would have been if the young man at Fred Meyer had introduced himself to the brunette holding a fern and a basket of coat hangers. If the woman in the Lloyd Center neighborhood had run after the guy with “the sexy beard and the hot cat vest” who rides his bike by her house every morning. They serve as a testament to what might be if she’d had the presence, if he’d had the courage, if they hadn’t been in a hurry or copied down their numbers wrong.

Gutowski does not normally shy away from social interaction, he says, but the circumstances weren’t right for a conversation with the girl on the bus. Still, he does not expect a response. “I never expect anything,” he says. “If you keep your expectations as low as possible, you can be happily surprised.”


Erick Reddekopp sips a coffee near the Dutch Bros. coffee stand by the Morrison Bridge. He comes to the stand every day on his way to work partly for the vanilla soy lattes, but mostly for the man who is working the window now.

“He’s a good-looking guy,” says Reddekopp, a heavyset 39-year-old. “There’s a really nice laid-back manner to him, which I really like. There’s a sense you get—the sense he’d be a fun person to hang out with and get a drink.”

The young man, who appears to be in his mid-20s, is wearing a black seashell necklace and knit toboggan hat as he serves espressos. During Reddekopp’s daily drive-throughs over the past few months, the two have developed a comfortable rapport. When the young man asked one morning what he was doing after work, Reddekopp gave a safe answer and then posted this ad:

Really nice, cute guy at Dutch Bros. by Morrison Bridge — m4m

I come by Dutch Bros fairly often. […] Never been ballsy enough to ask your name, but we always chat when you’re working. […] I have no clue sometimes if you are just a cool guy who’s just friendly or if maybe there is something more there. My gaydar is a bit off. Would not be opposed to hanging out beyond the Dutch booth though either way. […] love to hear from you.

Reddekopp tried Missed Connections because his other options for meeting men, including bars and the male-for-male section on Craigslist, seem tailored mostly to facilitate random hookups. He sent his message anonymously rather than in person, he said, because he doesn’t want to cause an awkward situation for the man at work—and he doesn’t know if he’s even gay.


The I-Saw-You ads published in the 1800s read remarkably similarly to those on Craigslist today. Take this ad, which appeared in the New York Herald in March of 1861:

On Wednesday afternoon a lady with a black silk hat walked nearly side by side with a gentleman in a drab overcoat […]. Both were annoyed by the wind and dust. Her smile has haunted him ever since. Will she send her address to Carl, Union square post office.

Mark Twain, who read his share of the ads at the time, wasn’t amused. “There seems to be a pack of wooden-headed louts about this town who fall in love with every old strumpet who smiles a flabby smile at them in a street car,” Twain wrote.

While Twain might say the same today, Missed Connections has accrued a following of loyal readers. Garrett Simpson, who moved to town with his girlfriend three years ago, considers Missed Connections “kind of a copout,” a dating service for people who want to force someone else to make the first move. Still, he enjoys the stories. He used to check the site regularly, purely for the entertainment value. As Simpson read, he would keep an eye out for references to places he frequents and people he knows.


Once, Simpson found an entry describing one of his friends.

Christopher Bayerle is a slight 26-year-old who often wears skinny jeans and canvas shoes. He had been out at Valentine’s, a chic hole-in-the-wall bar downtown, when he noticed a blond young man by the stairs. The two made intense eye contact throughout the night as Bayerle ordered drinks from the bar. The next day, Simpson found this ad on Missed Connections:

Looker at Valentine’s, Thurs, 7/16 — m4m

You, in jeans and a grey shirt, came in with another guy and girl. I was sitting against the wall, near the stairs. It seemed we were looking at each other a lot, unless you were eyeing my female friend… (that would be too bad.) And that smile, just as you walked out the door? More, please! Coffee or a drink sometime?

Simpson let Bayerle know. “It was really exciting,” Bayerle said. “It’s kind of like winning the lottery.”

He and the young man returned to Valentine’s a week later. Their meeting was relaxed, but the relationship didn’t go anywhere. “We just didn’t have anything in common,” Bayerle said.


Gutowski acknowledges he and the girl from the bus might discover a similar lack of compatibility if they ever encounter each other again. “I may hang out with her once and be totally turned off and not want to take it any further,” he said, “or who knows, maybe she won’t be into me.”

While Gutowski doesn’t have regrets about not talking to the girl face to face when he had the chance, he sees, moving forward, posting an ad as preferable to doing nothing. He welcomes the probability that maybe, just maybe, the girl will see the ad and write back.

“You’ve actually got to do it to know,” he said. “You can’t sit around pondering, ‘what if.’”

See the original in Willamette Week here.