Christopher Cantwell never asked to become a moderator of online dating site OkCupid. The site tapped him, without warning, and now he’s privy to private conversations, lovers’ tiffs, and the sometimes dark, often inane, unseen side of the online dating world.

Many OkCupid moderators are pulled from the site’s userbase and just six months after signing up for the singles site, Cantwell was elected to the army of arbiters who review posts flagged by OkCupid users and are tasked with marking the profiles “deleted,” “left alone” or “can’t tell.” Moderators can see comments from other moderators and how they ruled on an issue, but not who those moderators are or what ultimately happened to each of the posts in question. OkCupid’s arbiters of right and wrong also have access to the profiles of people who were flagged, though not the people doing the flagging. OkCupid did not respond to requests for additional information on how it works with its moderators.

What doesn’t fly on the site? There are strict guidelines for profile pictures -- no nudity, it must be of you (no "pets, cars, artwork, etc."), no extreme closeups -- and a predictable set of rules governing good behavior -- no spamming, no hate speech, no harassment, no "commercial solicitations," no “crude, overt sexual remarks" and no threatening messages.

Cantwell walked us through life as an OkCupid moderator and what happens on the side of the Internet most never see.

What did you have to do to become qualified to be a moderator?
Absolutely nothing, apparently. I’m not a very active user of the website and all of a sudden they notified me that I had been made a moderator. As far as I could tell, it was completely random.

What kinds of things do you see getting flagged?
Users can flag a profile and then the profile gets put into what’s basically a queue for the moderators to go through. And most of it is kind of frivolous. People report things like, “There’s a picture of their car” and I’m like, “I don’t care if they post a picture of their car, I don’t care what the rules are.” Out of a few dozen, I’d say I’ve only flagged two or three for deletion.

You mentioned that one of the things flagged was a series of private messages between two users. A man contacted another user, the “flagger," who said she/he wasn’t interested in him because he was too young for her/him. He responded with a terse “You’re pretty ugly yourself.” One of your fellow moderators weighed in with, “Not ban worthy, but he’s clearly a jerk.”

It’s remarkable that people have access to private messages, in some cases, and get to weigh in on them.

Yes. It is interesting that this person flagged a private message on a dating site and now it’s up for scrutiny by anonymous people who have apparently been chosen as moderators for no reason at all that I can find.

What have you learned about people since being a moderator on OkCupid?
I’ve learned that people are nitpicking and if they see something they don’t like, they’ll flag it for no good reason. For example, I’m looking at picture of woman in a driveway with dog and the picture is a little far away. So someone flagged the picture because it doesn’t show her face. I haven’t done a lot with it because most of the complaints, like this one, are total crap.

okcupid moderator
via ThatsNotOkCupid.com, a Tumblr of screenshots chronicling "the woes of a lowly OKCupid moderator."

Why do you think people bother to tattletale? And what does that say about how we behave online?
For the same reason that they vote for asshole politicians and 'cause all the other problems they cause in the world: because they’re assholes. I really have no faith in the human race. I look at this stuff, I look at politics and I think people are idiots and there’s just no hope for them.

What’s the strangest thing you’ve seen during your time as a moderator?
I’ve seen some nude photos, but I’m no stranger to that, and I’ve seen scammers. The worst thing I’ve seen is people asking for money and it looks like it’s bullsh-t. I used to work in a data center and I was responsible for the abuse department serving thousands of servers, so seeing scammers trying to rip people off could be off-putting for some people, but it's run-of-the-mill on the Internet for me.

In the course of your work in the abuse department you said you had to deal with everyone from spammers to child pornography purveyors. What would you do when you came across something illegal?
In the case of child porn, we would pull down the site and contact the FBI. Though there was one incident where the FBI demanded that we leave it up because they were running an active investigation on our networks and want to see who was accessing it. That was pretty disturbing. We told the site [hosting the child pornography] that the server had frozen up.

Besides that people are idiots, what’s your takeaway from your look behind the scenes on OkCupid?
I’m not taking much away from this except people are nosey busybodies.

Still, I would also say OkCupid looks like an okay site and you shouldn’t worry about it -- moderators are not deleting people for no reason, the complaints are pretty mild. There’s a shining little glimmer of hope for mankind.

This interview has been edited and condensed for clarity. For more on what goes on behind the scenes of OkCupid, check out the NSFW Tumblr ThatsNotOkCupid.com

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  • Don't Exaggerate

    Sometimes we embellish the truth, particularly when we want to impress a possible mate. But <a href="http://www.eflirtexpert.com/about-laurie" target="_hplink">Laurie Davis from eFlirt</a> warns us against exaggerating. "Overplaying your lifestyle will attract different matches who, ultimately, won't be the best fit for who you really are," she says. And <a href="http://cyberdatingexpert.com/" target="_hplink">cyber dating expert Julie Spira</a> agrees, also noting there is a huge difference between fibbing about your height vs. your martial status. "Single is single, and divorced is divorced," she says.

  • Don't Answer All Of OkCupid's 'Questions'

    One of OkCupid's features is a "Questions" section that allows users to reveal a few more facts about themselves. These factoids are then matched via an algorithm with other people who answered similarly. Questions can be answered publicly or privately, meaning your answers can be seen or hidden. But Spira thinks some questions are best left unanswered. She tells users to be careful with those that seem too political or sexual in nature because this data is all over the Internet: "You need to think every time you push the send button." She also says for public answers, you should "only pick the questions you would tell your mother [the answer to]."

  • Don't Assume The Right Person Will Magically Appear

    Davis says her biggest online dating no-no is complacency. "If you're not utilizing all the functionality a site offers, you miss out on the experience. Rather than complaining that you're receiving messages from matches you'd rather not meet, search and message some on your own," she advises. While this is true of all online dating sites, Davis stresses the importance of reaching out on OkCupid. "[It's]one of the fastest-growing sites, which is an advantage, but make sure you're not being lost in someone's search results by being proactive on your own as well."

  • Don't Use Old Profile Pictures

    If you're thinking of putting up a profile pic from 2004 -- reconsider. "They are going to look you up on Google; they are going to look you up on Facebook," says Spira of potential dates. "I think it's really important to have recent profile pictures. You're thanked a lot for being recognizable and having truth in the advertising." So skip out on that glamour shot from the '90s. And men -- most of us agree that the muscle shot in front of the bathroom mirror is an automatic "skip."

  • Don't Be A Rude Rejector

    Just like in real life, there are right and wrong ways to reject someone in the virtual world. "I don't believe in burning digital bridges," Spira says. "Why should you have to email someone and say, 'Hey you're not my type.' Dont say you're not my type -- you haven't met yet!" But if you really aren't attracted, Spira says just move on. Don't message them back, or simply thank them for the communication and wish them luck in their search.

  • Don't Check Your Profile Obsessively

    OkCupid's popular free edition of its dating service comes with a few catches, one of which includes people knowing when you check into the site. While possible soulmates won't know how long you've been online, they can view the time you last logged on. "It can be very obsessive and dangerous to your emotional health," Spira says about online daters who get addicted to flipping through OkCupid. For example, what if you go on a great date only to realize that 30 minutes after you parted ways, your date accessed the site two more times that night? Spira reminds users to "take a deep breath and don't jump to a digital conclusion."

  • Don't Withhold Too Much

    It's important to fill out OkCupid's "About" section to receive matches with similar interests. "Skimping on details will hurt you instead of help," Davis says. "The ultimate goal of your profile is to give someone a quick snapshot of your life. The more details you include, the more interactive your profile becomes, encouraging matches to message you because they enjoy the same activities." By adding a few facts about yourself, it's easier for possible dates to start conversation -- both virtually and in the real world.

  • Don't Come Off As Desperate

    Nobody wants to read on your profile that you've "tried this once before, but you're back one last time for more!" Forgo fishing for compliments or talking yourself down throughout OkCupid's "About" section, and let digital relationships run their course. Share information concisely and positively with people who match your interests ... unless you happen to be in the market for the desperate sort.

  • Don't Use The '3-Day Rule' Online

    "There is no digital equivalent of the 3-day rule," Davis says, noting our connected society has pretty much destroyed the idea of an ideal timeframe for response. "Today, responding quick doesn't necessarily mean you're pining away in front of your laptop all night. The OkCupid app sends notifications in real time, allowing you to compose a response quickly and easily, even when you're on the go." Both Spira and Davis agree responding in a timely manner is usually the best method to snatching up the right guy or girl.

  • Don't Obscure Your Intentions

    If you don't want to just hook up, and are looking for a little bit more in the relationship department, how do you present yourself? "What can seem sleazy to one person might be flirty to another. Make sure you stay on the right side of the gray line by keeping your intentions in check and acting according to what you're looking for," Davis says.

  • Don't Forget About The Buddy System

    There are a few instances where your friends should be involved in the online dating process. First, Spira suggest you have a buddy proofread your profile for spelling errors and accuracy. When you finally find a match, make sure a friend has the lowdown on where you're going for the evening. Online meetups in public places are common, but it doesn't hurt to have a friend know you went to see the latest movie, or that you plan on being out for a certain amount of time.