The Most Unconventional Dating Sites

by Spencer Bronson · July 22, 2011

At Guest of a Guest we've always been fans of HowAboutWe.com, a site where you propose date ideas and rank people by what they come up with rather than petty compatibility questions like on sites like OK Cupid, ever since we wrote about the site last year. Since yesterday we talked about some unconventional date ideas, what about some unconventional dating sites?

If you feel like you're looking for love in all the wrong places (and you got kicked off the hotties-only site you use, and you're not a huge fan of Apple products), maybe it's just that "normal people" aren't really your thing. "Woe is me," you might be thinking, but fear not! Thanks to the Internet, that magical, timeless universe where anything can happen, you're in luck! Here are some weird dating sites to help you meet the crazies of your dreams.

Women Behind Bars

If you're looking for the woman of your dreams to "Sing Sing" sing your passions from the mountaintop for without actually having to, you know, interact with face-to-face, then Women Behind Bars might be the perfect dating site for you. The site organizes personals by age and ethnicity (though curiously not sexual orientation). Meet hotties like Amy F7922 from Michigan, who is in prison for life but willing to relocate, who says "I'm looking for my soul mate" and "I'm in need of someone who has knowledge of juvenile laws in the State of Michigan prior to 1990." Many of these women are just looking for a pen pal, so don't let Amy's plea for legal assistance deter you! Just don't expect too many conjugal visits.

420 Dating

If you define your life by what you smoke (Didn't mom tell me "You are what you blaze"?) or otherwise consider your dream date to be "Let's burn a fattie and watch TV with a bowl of chips between us" (Or you live your life by the doctrine of Puff Puff Pass, or you worship either Jack Herer or Jah) then stop reading this article right now and click that link because you're seconds away from meeting your new partner. Plenty of stoners are desperate and lonely, so this site should be filled with potential mates ripe for the picking.

Trek Passions

How big of a Trekkie are you? Do you feel like you can't spend another moment of your life without someone to share your obsession with? Trek Passions is sort of the classic strange dating site; as you can see above, their actual slogan is "Live Long & Prosper." They follow me on Twitter, though I'm not entirely sure why, because I don't even speak a lick of Klingon! If you're interested in cultivating a healthy relationship based on your mutual passion for the hit sci-fi franchise, look no further: You're about to boldly go where no man (rather, you) has ever gone before. Is there a Star Trek equivalent to the baseball metaphor for sex? You could make it all the way to... uh... I dunno, the bridge of the Enterprise?

STD Friends

If you have (or want, I guess) certain medical issues that turn dating new people into an elephant-in-the-room kind of situation, I suppose you can feel more at ease with people you meet on STD Friends, where you can search people by criteria like oral or genital herpes, HPV, HIV and Hepatitis B and C. The site also has fun features like forums and polls. (The most popular answer by far to "At the end of your first date what happens?" is "Sex"; the most popular answer to "Do you have sex on the first date?" is "All the time"; the most popular answer to "What are you looking for on STD Friends?" is "Hooking up.") The site has a wider scope than its alternative, the herpes-and-HPV-only site MPwH, which has been around for 13 years.

No Longer Lonely

Rounding out this list is by far the most depressing dating site out there, No Longer Lonely, which caters specifically to people with mental illnesses. The "crazies" comment I made earlier may seem insensitive in this light and mental illness is certainly a serious issue that many people struggle with every day, but can you imagine the shit show that must be a website devoted to forming relationships between mentally ill people? Everyone has their fair share of "psycho ex" horror stories—so, hey, let's see what happens when they all date each other!