Interface to Interface: A guide to Craigslist dating 

“I went on the worst date of my life last night,” exclaimed a friend one evening over falafel sandwiches. We all leaned in to listen—everybody likes a good “worst date ever” story. “He showed up to the bar 30 minutes late, didn’t have enough cash to pay for a beer, and he looked nothing like his picture,” she griped. Before we could say anything, she snapped, “Yeah. It was a Craigslist date.”

I’ve noticed an ongoing trend with my friends in San Francisco: Everyone wants to Craigslist date, but nobody seems to be having any luck with it. It makes me wonder why people use a site that is also used to announce yard sales and job listings to find a date or even a long-term relationship. Can you form a successful, healthy relationship from a Craigslist date? And why Craigslist and not one of the thousand dating sites the web has to offer? I wasn’t surprised, however, when my friend, who is new to San Francisco, told me he was going to make a post on the Craigslist m4w forum. I sat down with a few Craigslist dating veterans living in San Francisco, the birthplace of Craigslist, to try and figure out what the allures and pitfalls are of the site.

What do I have to lose?

Twenty-six-year-old *Anthony had no problem making friends when he moved to the city, however he had a difficult time meeting girls outside of his circle. With little dating experience, Craigslist seemed like a logical strategy. “It makes sense…,” he says hesitantly, “in theory.”

*Cynthia, twenty-five, had just gotten out of a relationship when she moved to San Francisco and hadn’t dated in awhile. Still hung up on her ex-girlfriend, she wanted to meet new people but wasn’t sure how to go about doing that in a new city. She took a “what do I have to lose” attitude and started to browse the dating forums. “If you’re also really wanting to be in a relationship, just the act of putting yourself out there...sometimes it can make you more bitter, sometimes it can make you more relaxed,” she says.

Anthony agrees that Craigslist is a good way to gain dating experience. “I think that was a large part of my motivation [for going on Craigslist],” he recalls. “Going on successful dates makes you more confident.”

*Allison, thirty-four, wasn’t having any trouble meeting people or finding dates. She started using Craigslist, however, because it made dating “easier and quicker.” It enables you to cut out many of the steps of the dating process—finding somebody in a bar or any other scenario, approaching them, and then asking them out. You can just click on an appealing ad and you’re halfway to finding a date.

A dating free-for-all

Unlike other dating sites, Craigslist doesn’t have the technology for users to create a structured profile with a photo. There’s no specialized dating forums by race or religion (like Blackplanet.com or Jdate.com). It is also free and you don’t need to be a member to post or respond to personals. This is the reason a lot of people sign up for Craigslist—you don’t have to submit personal information so you can be as anonymous as you like. The openness of the website, however, can be intimidating for some.

Anthony only posted ads and developed his own method of attracting responses. “I had a strategy of making the most deliberately stupid ads possible. I would just attach an image, but it wouldn’t be of me. People are more apt to respond to ads with images attached,” he claims.

Cynthia, on the other hand, only replied to ads she thought matched her interests. She couldn’t bring herself to make her own ad because she just wasn’t sure what she was supposed to say. “There’s a certain image you want to convey and it’s really hard to figure out what that should be. I like referring to what they posted and then asking open questions,” she says.

Allison posted her own ads and responded to others. However, most of the replies she received were “scraping the bottom of the barrel.” She estimated that about 60 percent of the responses she got had a picture attached to them, usually of the pornographic variety.

Flakes and photo thieves

The anonymity and openness of Craigslist can pose other few problems. Both Cynthia and Anthony agree that people who Craigslist tend to be a lot flakier compared to those on other dating sites. Because Craigslist is free and anonymous, people are able to get away with being noncommittal, Cynthia believes.

She theorizes that most people who are looking for dates on Craigslist don’t actually want to be dating. Craigslist enables you to begin the process of dating, but also allows you to not follow through with it. She refers to this phenomenon as “half-assed dating.” “There’s some hang up of meeting someone in person,” she says.

Her date had problems with Craigslist flakes before, so she required Cynthia to go through an intense screening process where Cynthia had to answer important questions such as “Levi’s or Wranglers?” and “iPod or CDs?” in a survey before they went out.

Allison noticed another problem with Craigslist: users stealing other people’s pictures. She noticed pictures being recycled over and over, reincarnating in different ads. She warns others of posting pictures of themselves on ads. You never know who could see it and, worse yet, you never know where it might end up!

From Craigslist dating to casual encounters

Allison determined that Craigslist was better used as a hook-up site than for dating or romance, so she began to browse the casual encounters forum. She would post her own ads and reply to others. When she perused other ads, she’d look for a few essentials: a sense of humor, correct spelling, and some personality—much like she would if she were looking for date. “A picture and then ‘I’m horny’ isn’t going to get you anywhere,” she advises.

She would use email and name aliases and communicate with the men over email and the phone before she met them. However she never showed them any photos of her face. Before she left, she would give the guy’s contact information with her roommate. And though she never had to use them, she’d carry a flip knife and pepper spray with her.

She hit if off with one of the guys she met through casual encounters, and they dated for about three months. After awhile, he got overly persistent and she broke things off with him.

In a large city that often seems quite small—i.e. San Francisco—she ran into him about six months later and they started dating again. One day she decided to swing by his work to bring him a smoothie and caught him with the casual encounters forum up on his screen. “Wasn’t I enough?” she thought.

He made up some excuse, but she began to see how addictive the casual encounters forum was. She started to recognize certain posting styles and pictures and noticed that the same people were posting over and over. It got to a point where she would check the forum religiously when she got home, putting responsibilities, like homework, aside. Finally, after a string of bad meet-ups, her roommate looked at her and said, “What are you doing? You’re just meeting dirt bags.”

Finding exactly what you’re looking for

Twenty-six-year-old *Kat was not looking for a relationship and especially not on Craigslist. She had just gotten out of a long and stressful relationship with a woman and was upset and disillusioned. She was spending all of her time focusing over every little detail of went wrong and wanted to get out of that mind set. One day when she was casually browsing Craigslist to keep her mind off her ex, she stumbled upon an ad in the m4w section that caught her eye: “Lesbro seeks fag hag.” *Sydney, twenty-six, described himself as a person with a lot of queer friends who had trouble meeting heterosexual women. He wanted to find a woman who understood the queer culture and was also interested in a romantic relationship.

“What I thought I was looking for in a relationship was described in the ad. Which was an unusual circumstance,” she remembers. Kat had identified as a lesbian for many years, but became interested in dating men. The ad appealed to her because she wasn’t quite ready to be in a “straight” relationship.

When she first saw Sydney’s picture and MySpace profile, she wasn’t sure if he were her type. She was so attracted to what he said in his ad, however, that she decided to give him a chance. Their first date took place at a local bar (ironically, a lesbian bar, though they didn’t know that at the time). It was a little awkward at first, but they realized they had many things in common beyond what was written in the ad. Within a few days, they arranged a second date and have been together for about six months.

They’re very open about telling people they met off of Craigslist and it doesn’t really play any part in their relationship. “I think it’s because we met shortly after responding to the ads. I think if we would have had a lot of email correspondence it would have been a lot different,” Kat says.

The one issue they have that seems to be related to Craigslist is that they have trouble getting to know each other’s friends. “They didn’t have any context to give me. I was just somebody from the Internet and I think he had the same problem,” she says.

I would/wouldn’t recommend it

Many of Kat’s friends started using Craigslist to find dates after seeing how well it worked out for her, though she admits that she hasn’t heard many success stories. She still recommends it to other people and says that if she ever found herself single again, she would definitely use Craigslist again. “I kind of have an idea of what I’m looking for—a concept of similar interests and it’s not something I can easily find through other relationships, so Craigslist has been a good catalyst for forming these sort of romantic relationships.”

Allison and Anthony say that they will definitely never use Craigslist to date again. Allison is currently going out with somebody she met through a friend—not through Craigslist. So far, it’s going really well. Anthony has temporarily sworn off dating and thinks his negative experiences with Craigslist mostly play a part in that decision.

Cynthia has since switched to other dating sites because she was so tired the flakes on Craigslist. She wouldn’t dissuade someone from using Craigslist however. “I think it’s a really good way to spend an hour or two deciding if you want to start dating or not.”

And even if you can’t find a date, maybe you can find your dream job or a good deal on a used sofa.

*Names have been changed to protect identity.