How does the chaos of Craigslist love endure in an eHarmony world?

craigslist loveCraigslist is many things to many people: To the modern Internet denizen, it’s an unsightly holdover from Web 1.0. To the open-source advocate, it’s a locked up, selfish, overflowing database of information that’s anti-innovation. And to some of us, it’s where the magic happens.

While you and I might browse Craigslist to find a new apartment or a gently used (fingers crossed) couch, there are many, many more people using it to look for love.

But why? In a world where we have innumerable dating websites, applications that tell us if someone is right around the corner, and social networks that make it beyond easy to browse for a potential new boyfriend or girlfriend, what would ever compel us to turn to Craigslist? It’s ugly, it’s arguably broken, and you know, there’s that whole Craigslist Killer thing. I mean, if there is a Lifetime movie (especially one featuring the incomparable Billy Baldwin) about the dangers of something, as a rule of thumb you probably should avoid said thing. (Looking at you, teenage pregnancy and experimental drug use).

At one point, I was paying hundreds of dollars a month to date.

Enter the Craigslist Conqueror, real name Aaron Smith. After a divorce he didn’t see coming, Smith found himself more than a decade out of the dating game and very, very alone. “I tried every dating site out there,” he tells me. “The problem is that it’s too easy to see a picture and keep moving.” Smith describes himself as a moderately attractive but not exactly eye-catching guy – one, he says, that is easy to just skip past. “I could craft a great bio, but so many people just take one look and keep moving.”

He lists the myriad of other dating site dilemmas: You find someone you connect with, but they live too far away for anything to develop. They haven’t logged in to their accounts in months. And perhaps, most discouraging of all, the cost. “At one point, I was paying hundreds of dollars a month to date,” he says.

His frustration isn’t unique: One friend who’s given the online dating scheme a go has similar complaints. “The worst part about it is definitely the cost… Aside from that, learning how to actually effectively use each site is tough. Different types of people are on different sites and it’s tough to find the type of person you want to date, quite often.” He also says that it’s more than common to never heard back from a person you reach out to, and that even those who do respond, the odds of getting them to go on a date are less than 50 percent.

After Smith’s failed and disappointing attempts at using dating sites, he turned to Craigslist Casual Encounters. “I was watching the news and there was some story about Craigslist Personals, and I figured, why not.” He says after initially writing up a rather tame profile describing himself as a nice guy with a great sense of humor, he received zero responses. “It was like crickets,” he says.


That’s when he decided to just go for it, writing ads designed to make a lady go weak in the knees. And it worked. The ads varied: “Sometimes I’d write them as a man that just wanted to dominate a woman and make her feel submissive. Other times, I’d be the loving guy that just wants to please you and make you happy all night.” Whatever character he decided to play, he got results. At one point, he tells me he was sleeping with two to three women a week, sometimes more. And thus, the Craigslist Conqueror was born.

But he realized it wasn’t him: It was his methods. “I would buy romance novels and glean details on how to appeal to women… and so I started telling my friends about it,” he says. “And they did even better. I thought I was Superman – but I just had the right tools.” That’s when he started sharing his secrets, via his book and even on the Howard Stern Show.

While his time conquering Craigslist was originally of the sexual variety, Smith ended up finding love on the site. He’s been in a relationship for some two years with a woman he met using the site, and says friends who’ve used his system have found serious, committed relationships as well.

If Craigslist Casual Encounters is the equivalent of writing your number on the bathroom door of the bar, then Missed Connections is like putting a love note in a bottle and hoping that one person finds it. More than 60 million people in the U.S. use Craigslist each month. As of late 2012, it was pulling in 50 billion page views a month. It has an Alexa rank of eight. Suffice it to say that the odds of reconnecting with that stranger you made furtive eye contact with across the bar are bad.

I figured, what do I really have to lose besides the five minutes of my life it took to write and post the thing?

But… what if they aren’t? The Missed Connections success stories are surprisingly many – and unsurprisingly, inspiring. Our own Jen Bergen is one of these lucky souls. She tells me that after locking eyes and dancing with a mystery man at a concert, he disappeared into the crowd. “The next day, I thought, ‘what the heck? Why not try Missed Connections,’” she says. “I figured, what do I really have to lose besides the five minutes of my life it took to write and post the thing.”

As a New Yorker, she didn’t expect anything to come of it. But the next day she got a response from the man himself; his friend had noticed the Missed Connections ad and pointed him toward it. “Neither of us had ever done anything like [that], so it was a bit awkward at first,” Bergen says. “We met up a few days later for our first date and the rest is history.” The rest being that the two have been together for nearly three years. She mentions she knows two other couples who met thanks to Missed Connections, and one of them is now engaged. 

“I knew it was a long shot, but Missed Connections is the first place people go when they want to find someone they had a fleeting moment with on the subway or in a coffee shop,” she explains. “Plus the anonymity thing is a big part of it.”

And therein possibly lies the catch: The guarantee of remaining undercover offers us the confidence to pour a piece of our hearts out to that stranger we felt a spark with (or find someone who wants to share a steamy, no-strings-attached sex session for a night).

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