User menu

Main menu


The History of Creepy Online Dating

From AOL chatrooms to Craigslist to ChatRoulette, weirdos just won’t go away

Looks like someone just discovered our Found Porn tumblr blog... 

Through Internet history, there’s always been a slightly creepy aspect about meeting people online for a romantic hookup. Sure, it’s common now, but the very term, “online dating” still has a bit of a stigma about it, mostly thanks to the types of oddballs who, in fairness, would also ruin most other kinds of social interactions (if they ever left their house). Over the last 15 years, simple dating chat rooms on Yahoo and AOL have evolved into the new wave of live social mixers on sites like SwoonXO, where people with common interest connect via webcams. Dating sites are big business and growing (IAC’s - which also owns, People Media and Singles.Net - purchased OkCupid for $50 million in February this year), so join us as we journey through some of the more questionable moments from the history of online dating. (Want to hold hands? No? Ok.)

Started: 1996
Back in the dark ages of the Internet this sounded revolutionary: AOL Chat Rooms allowed groups of people with similar interests to convene and type conversations in real time. Theoretically, it was just like real life, except that you had to HIT CAPS LOCK TO SHOUT AT PEOPLE.
Creepy Outcome: One small problem: you never knew if the woman you were chatting with was actually a dude with a hairy back requesting that you touch yourself. Also, poor typing proclivities usually left love-seekers out of the reindeer games, cursing their slow fingers. Eventually AOL Chat Rooms devolved into a forum for webmasters to sell online porn.

Started: 1996
You have to love the women who post free dating personals on Craigslist; it’s a regular pictorial barnyard of human curiosities. And we mean barnyard.
Creepy Outcome: For those looking for love and romance, Craigslist personals might not be entirely the wrong amorous avenue: Most of the ads that appear written by horny women seeking men are usually written by prostitutes—you can hook up with them, but it’s going to cost you some bucks…or your life! Yep, that’s another serious drawback of Craigslist online dating: people sometimes end up getting murdered. Yikes! To avoid this situation, make sure you know who you’re corresponding with on Craigslist. A quick ice-breaking question to ask: Will you eventually murder me? (Hint: only murderers say “no”). Alternatively, agree to meet in daylight at a crowded café. And bring an axe.

Started: 1997
If you prefer a captive audience, Women Behind Bars is for you: featuring profiles of hotties who are incarcerated, it’s ideal for guys who like to know where their girl is on a Saturday night (and every other night. For the next five to eight years). That’s right, your next love-spark could be a murderer or drug addict! Just to make it very clear that these are not your average, law-abiding citizens, the Warning Page of Women Behind Bars says the following:

“First you need to keep it in mind that these ladies are in prison and most for good reason.
Here are some of the problems we have encountered:

Frankly, these offenses sound pretty minor compared to whatever it was they did to get their asses flung in jail in the first place, but whatever.
Creepy Outcome: Women have told men they are about to be released and that they need money wired to them for a plane ticket. After the transaction, the jail honey never corresponds again. But why not, right? What do these women have to lose? They’re already in prison!

Started: 2000
eHarmony is a Christian-founded dating site that claims to have a "scientific" approach to matchmaking. Maybe that’s why when you fill out their questionnaire, it makes you feel like you're taking a Scientology E-meter test. From below, guess which question is eHarmony’s and which is from a Scientology personality test:

I often leave a mess in my room.
a) Not at all
b) Somewhat
c) Very

Do you linger when you eat?
a) Yes
b) No
c) Somewhat

If you are confused: the first question is from eHarmony and the second is from a Scientology personality test. Both will probably end in a crappy date.
Creepy Outcome: You’ll probably find someone to practice sexual abstinence until marriage with, while discussing aspects of the Planet Xenu. As with all online dating sites, the problem is the profile photo: date-seekers sometimes post images that are over a decade old. A good way to combat this problem: have your potential love connection send a photo holding a copy of a newspaper with today’s headlines. Is that too much to ask?

Started: 1999
Daily Diapers is a dating site for adults who like to wear diapers. And…that’s all we need (or, indeed, want) to say about that.
Creepy Outcome: YOU END UP IN DIAPERS. If you don’t find that creepy, well, we’re cool with that, but…man, you creepy.

Started: 1999
This is the dating site you join after you’ve had enough Craigslist-related doctor visits. Not only can you cruise women’s profiles, but you also learn what type of STD they are suffering from. Is it genital herpes or HSV-2? One thing’s for sure: you know that these lovely ladies put out!
Creepy Outcome: STD Friends offers a relationship that will stay with you—forever!

A trip down Chatroulette Lane is an experience that mostly involves being exposed to a multitude of guys whipping out their junk. The site is a revolving live-cam chatroom that brings together people from around the world. Think of that magic chemistry: one minute you can be talking to a hot girl from Georgia: the next, it could be a white supremacist from Idaho. And then some guy whips out his junk. And then another guy whips out his junk. And another and another. Then, just when you think you’re immune – a girl whips out her (male) junk.
Creepy Outcome: A webcam on a dating site is a magnet for a virtual pickle-party circle jerk. Some sites like SwoonXO and Woome try to snip the penis problem by making users create profiles, but Chatroulette, with the webcam feature on its front page, is the Wild West of live social networking-- deviant behavior is the unmonitored norm. Talk about junk mail!

This site sounds like a plan for a better Aryan tomorrow (or a Marilyn Manson GeoCities page). It’s no surprise that this douche-y supremacist site only allows “beautiful people.” Sorry, uggos—go find another site like
Creepy Outcome: Members have been booted off Beautiful People for packing on extra pounds over the holidays. The founder of the site said, "Letting fatties roam the site is a direct threat to our business model." Which, surely, is only true if the site in question is a kitchen, and your business is selling cakes?

Harmon Leon is a comedian and author of six books, including The American Dream.