The Future

A love story that started on ChatRoulette

James and Karen met on a more serendipitous version of the internet. Where there were a lot of penises.
The Future

A love story that started on ChatRoulette

James and Karen met on a more serendipitous version of the internet. Where there were a lot of penises.

In October of 2011, James Greenwood was playing Chatroulette, the website that pairs users around the world in video chats with other users at random. Though not a habitual Chatrouletter, Greenwood, then 21 and a student at Cardiff University in Wales, had used the app before with his friends. Once, they’d left Chatroulette running in the kitchen at a house party. Though they liked to peer into living rooms and offices around the world via Chatroulette, it primarily facilitated a laugh for those people together IRL, on the same side of the camera.

Karen Bird, then 18, was also on Chatroulette that night at her home in Cincinnati. A recent high-school graduate about to begin cosmetology school, she also rarely used the site; it was primarily a social activity to enliven a dull evening with friends, the way a prank call can spice up a sleepover. Karen and her friends knew the risks of using the site — an outsize proportion of Chatroulette users tended to be exhibitionist men, and the site became known for people flashing their genitals. If Karen and her friends saw a penis, well, that was a penis they all saw together.

Karen and her friend Tera had already been on Chatroulette for a few hours that night, occasionally fielding and rejecting requests to show men their tits. James’s friends, a few hours ahead in the UK, had gone to bed after a somewhat bland session. But James stayed online, putting off coursework and looking to chat.

Then, his face popped up on Karen’s screen.

“Oh,” Karen remembers saying to her friend, “we gotta talk to him.”

The microphone on James’s webcam was broken, so, after exchanging smiles, James typed questions while Karen and Tera answered using the video camera.

“If he gets his dick out, I can always leave,” Karen said she thought at the time. But, to her relief, his dick stayed in his pants. After an hour, Tera went to bed, sensing that there was a deeper connection between James and Karen. The two continued to talk for three hours.

“It was crazy,” Karen told me. “We were like, the same person.”

James stayed up deep into the Welsh night typing out questions for Karen and writing responses to her verbal queries. Chatroulette allowed users to export the messages afterward, but not the video playback, so they have James’s one-sided minutes of what they consider to be their first date.

“If he gets his dick out, I can always leave,” Karen said she thought at the time.

That night, they exchanged BlackBerry Messenger pins, and BBMed all day for the next week. Soon after that, James got his laptop mic fixed and the pair exchanged Skype information. For a month, he’d wait up every night after school for Karen to finish work, and they’d videochat late into the night.

“I could tell him anything.” Karen said. “I knew there was no way this was going to pan out so I was really open.”

By Halloween they’d become so inseparable that Karen remembers leaving a party to Skype with James.

“I’d rather be talking to him than anyone else,” she said. “Which was actually kind of overwhelming.”

But Karen got scared. Nobody warns you that meeting someone thousands of miles away over the internet can lead to… accidentally falling in love with someone thousands of miles away you met over the internet. “I thought, this is never going to go anywhere, so what’s the point of me missing out on spending time with people I actually know?” She told James she thought it would be better if they didn’t talk anymore.

“I was gutted,” James said. “But I guess I knew she was right.”


Founded by then-17-year-old Muscovite Andrey Ternovskiy in 2009, Chatroulette offered users travel, escape, and the emancipatory thrill of anonymity. The ubiquity of webcams (the MacBook released in 2006 had a camera; Ternovskiy, a PC user, bought an external cam for $10) had brought joy to every Boca Raton-dwelling grandmother dying to see their grandkids in New Jersey, but for Ternovskiy, the novelty of seeing his friends from afar had worn off.

“My friends and I used to video chat over Skype quite often, but that got boring after a while,” told Der Spiegel in 2009. “I always knew who was waiting for me and who I would be speaking to.”

Seeking a way to make random contact with people around the world and finding nothing, Ternovskiy coded a tool himself. It was free, and simple: go to the url and turn on your camera. Chatroulette quickly exploded from 500 users to 50,000, and at one point had more than a million users daily. People were enamored by the site: Wired wrote about the ability to meet people “from Florence, to Sao Paulo, to Little Rock, to Shanghai”; Union Hall in Brooklyn hosted a party where Chatroulette was projected on the wall and people took shots every time they saw a penis; the artists Eva and Franco Mattes displayed a fake suicide-by-hanging on the site and recorded ‘rouletters reactions.

Sure, Chatroulette was international, and allowed for chance encounters, but the promise of anonymity, chaos, and lack of supervision draws a specific crowd. According to a 2010 study by TechCrunch, 89 percent of the users of the site were male and 13 percent of the “spins” on the site yielded a dude jerking off. South Park parodied the site in an episode where Cartman and Kyle logged on and saw only penises. Where Facebook was the uncomfortable office party/family reunion of the internet, Chatroulette was a meeting of the UN, but 1/8th of the delegates had their dicks out. This explains why, well before October 2011, when Karen and James first met, the site’s usage had declined precipitously; a 2010 Salon article headlined “R.I.P. Chatroulette, 2009-2010” noted that, “a few months ago, it was the web’s hottest trend. Then users took their self-exposure way too far.”


A year after Karen and James first met, she logged onto Facebook, where they were friends. She saw James was online via Facebook Messenger, the AIM-killer that the site had integrated into their service that year.

“Hey,” she typed. “Long time no talk.”

Just as fortune had first rouletted Karen into James’s life, this reunion was perfectly timed. James, in Wales, had graduated and was suddenly untethered to the UK. To Karen, this signaled that a relationship that once seemed “pretend and pointless” now had the possibility to become “something totally real.”

After a few months of video-chatting — this time he even met her parents over Skype — James, who had been saving up money to go to South America, went there with the intention of backpacking for three months and then heading to Karen. He made it three weeks before decamping for Cincinnati, where he stayed with Karen and her parents — in the guest bedroom — for 90 days, the duration of his tourist visa.

James and Karen, with their daughter Poppy.

James and Karen, with their daughter Poppy.

James said it wasn’t awkward to disclose to others how he and Karen met. If an inquiring mind “didn’t know what Chatroulette was, then they’d just nod like it was any online dating site.”

“But if they knew about Chatroulette,” Karen smiled mischievously, “they’d freak out like, did he have his dick out?” (“I didn’t!” James insisted).

If at first they were embarrassed by the questions and evaded telling their origin story, now they relish the opportunity to tell people how they met. “I love it when people ask,” James said. “The response is always excellent. So now I’m like, well now I’m about to tell a killer story.”

Perhaps James and Karen’s story plays so well because it feels like folklore from a previous iteration of the web. As the internet is winnowed down to a few gargantuan, all-seeing websites, it feels a bit fantastical that something so “random,” so pure, can happen online. Around the time they met, still-new social networks like Facebook allowed users to update friends and family while hiding intimate details behind the friend-request firewall. Likewise, the then-three-year-old Twitter was used to follow people, ostensibly friends and public figures you were interested in, and in turn created a persistent epistemological record for everyone from your next door neighbor to the restaurant chain Denny’s.

“I love it when people ask [how we met],” James said. “The response is always excellent.”

By siphoning users from the maelstrom of internet chatrooms — in which random, anonymous encounters abounded — they have enclosed people in their preexisting social circles. What these social media platforms lacked was the old internet’s id, the chaotic, random, anonymous, and often prurient spaces that typified the early internet. Sure, social media made it easier to keep up with friends, but you couldn’t meet strangers, tell secrets, and wile out like you used to. In protecting users from creeps, phishermen, and scammers, the internet has lost a feeling of serendipity.

James left Ohio in the summer of 2013 and Karen soon booked a flight to visit him in the UK, where she stayed for a month. After traveling back and forth, James relocated permanently to Ohio. They were married in 2014 in a ceremony at the Cincinnati courthouse, followed by a small celebration with friends and family.

Karen, who works as a manager for Free People, and James, a fraud investigator at Barclays bank, remain in Cincinnati, where their family has grown. In July 2018, James and Karen welcomed daughter Poppy, who with her blonde hair and bright blue eyes is without question the cutest thing Chatroulette has produced. Karen said she’s not worried about explaining how she met James to Poppy. “I think we will probably just tell her," she told me. ”You don’t always meet your partner in the most conventional way anymore and that doesn’t mean it’s not special.”

Poppy, hanging out.

Poppy, hanging out.

One afternoon, after FaceTiming with Karen and James while Poppy was down for a nap, I logged onto Chatroulette, which is still up and running, if somewhat lethargically so. After landing on a man flexing his pecs, two penises in a row, and a guy in Germany who graciously asked if he could show me his dick, I was paired with a handsome young man who said he was from Turkey. He told me to guess how old he was and I did, correctly, 24. I told him we were the same age.

“You look much older,” he said. “No offense… But I like your blue eyes.”

Zoe Dubno is a writer from New York.