Dating Site Secrets: I Was Paid By a Dating Site To Make Men Fall in Love

If you’re a female who’s ever used OKCupid and the like for any amount of time, you’ve probably received your fair share of absolutely creepy messages. In fact, I’m guessing many of you men have, as well.

Now, imagine having to respond to every single creepy message you’ve ever received on a dating site – with the goal of making them fall in love with you. 

When I was 20 years old, I was paid to do just that.

Now I’m sure you’re wondering: who would pay me to do such a thing? And more importantly, why would I do it?

Let’s rewind a bit. In fact, let’s go wayyyy way back… to 2003, when I was 20 years old. At the time, I was temping at a small mortgage company by O’Hare, covering for a woman who was out on maternity leave. My duties were simple: answer the phone. Take in the mail. Sit at the front desk and, well… keep the seat warm and try not to fall asleep.  At that time, the economy was still in its post-9/11 slump, people weren’t buying many houses, and as a result? I was bored out of my mind. No matter how many times I asked, no one would assign me extra duties. I ended up spending my days on AIM and reading message board after message board after message board. In short, I’d like to go back in time and smack myself – my ass should’ve been going to college, not wasting time in a shitty job… but I digress.

One day, I came across a job posting online – a dating website was looking to hire community managers. Back then, “community management” was limited to moderating comments, posting messages and basically making sure people weren’t going batshit crazy on message boards. I applied, figuring this was something I could do to distract myself while bored at work. (Clearly my ethics weren’t all that great at age 20.)

Low and behold, I got the job.

The job seemed simple enough:  I was to make a profile on their site and “make new members feel welcome” … whatever that meant. I poked around on the site to make sure it wasn’t anything sleazy and confirmed that it was just a basic, normal dating site – not unlike OKCupid or Match.com. I was offered flat pay of $300 per week – not bad for a side gig I was doing while at work. Once I had already signed the contract and had finally received full instructions, it hit me:

I had just taken a job as dating site bait.

Once per day, this website would send messages to men on my behalf. Not just a few – thousands of messages. Why? Simple: it was free for women to join the site. Men, however, had to pay. In other words, men would register for the free account, see they’d received a message from a cute 20 year old girl, curiosity would get the best of them, and they’d pay for membership.

Yeah – pretty bad. A brilliant growth move on their part – but ultimately, just kind of awful and morally questionable.

I questioned this, and was told by the founders of this site that this was perfectly legal, and that all of these men had been informed that I was simply an “online ambassador” for their site. “In fact,” they pointed out “your profile will even blatantly say ‘Online Ambassador’ – so you shouldn’t be concerned.”

With that reassurance, I dove right in.

On the first day, I actually thought it was kind of fun. I had received about 70 messages – totally manageable – and spent my day at work typing thoughtful responses to each message.

Day two? A little hectic –  I received a few hundred messages. Still, nothing too crazy – and it was keeping me occupied.

By day three, however, things got… intense. I had received over 500 messages – and in order to keep the gig, I had to respond to each and every message within 24 hours. According to my “manager”, the ultimate goal was to keep these men as paying members for as long as possible. In her words, I was supposed to string them along, get them to keep logging in, and ultimately – make them fall in love with me. However, I was never to provide any personal contact information, so they’d have to keep paying their membership fees just to maintain our “relationship” …yes, terrible.

The number of messages I received each day grew higher and higher until I was receiving a few thousand messages each day. Each night, some sort of message (I never did find out what it was) was sent out from my profile to every single man that had ever registered for the site, but had either cancelled their paid membership, or never paid to begin with. On top of these messages, I began receiving responses from men I’d already responded to. It was overwhelming – and at this point, things began feeling very, very… skeezy.

I’d receive messages from older, married men who alluded to paying me for my companionship. One in particular that sticks out in my memory was a very persistent 56 year old married doctor who looked like Santa Claus. He lived in Milwaukee, visited Chicago often for business, and wanted to put me up in a luxury apartment on Lake Shore Drive. He reasoned that it would be doing us both a “favor” – he’d be providing me (in his words, “a struggling young woman”) with a free Gold Coast apartment. In return, he’d no longer have to stay in hotels when he was in town, and he’d “no longer have to feel lonely when visiting” because he’d have a place to sleep… and someone to sleep with. And, he swore, his wife wouldn’t mind, because she worried about him spending all of that time alone. Right. 

Unfortunately, no matter how strange or creepy a man was, I had to respond, or I was fired. Since they weren’t actually reading the messages I was sending to people, my tactic was that I’d be as annoying or stupid as possible to scare the creepy ones away.

By the end of the first week, I was feeling downright… dirty. I was receiving so many messages at that point that at the beginning of each day, I’d simply type up the most vague message I could think of – something so general and boring about my (fictitious) life, that men wouldn’t realize they were simply receiving a form message.

A few smart men caught on immediately and became (justifiably) angry. When that happened, I was instructed to simply point them to the Terms of Service they had agreed to – buried within paragraph after paragraph of legal jargon was a line they had snuck in that made users aware of the fact that they may receive messages from “online ambassadors” that are paid to interact with members.

Oh, and that “Online Ambassador” logo that was supposed to appear on my profile? Was actually a tiny, well-hidden graphic that said “OA” – and out of every single person that contacted me, only two men ever questioned what that meant.

As creepy as this all was, oddly enough, there were a few positive moments. At times, I felt like I was brightening the day of some men that needed it. I’d receive messages from people who were physically or mentally disabled, and I’d be sure to take the time to actually talk with them, send them real messages, be a friend, listen to their problems, and offer advice.

In every single case, that’s all they were really looking for – a friend to talk to. Most of them began confiding in me about how lonely they felt, which broke my heart. Sometimes, there were elderly men who had lost their wife and missed having someone to talk to. Ultimately, it was the men who were extremely lonely that would maintain correspondence with me. All for the low, low price of $49.95 per month.

What it boiled down to was this: I was essentially a virtual escort for thousands and thousands of terribly lonely men – and a sleazy website was making boatloads of money off of it.

After a short while, I no longer felt safe. While much of the information I used was fictitious (namely, the little details I provided about my day-to-day life), there was enough real information about me posted on my profile for things to get creepy. According to the rules, I had to post at least 10 of my own pictures – and they all had to clearly show my face. Additionally, I had to use my real name and basic info – location, age, etc. There were a few creepy men who became obsessed with finding out my personal information, and would send me message after message trying to guess specifically where I lived, where I worked, etc.

By the end of the third week, I couldn’t handle it any more and quit. Not only did I feel unbearably guilty for leading these men on, but I felt dirty – and I didn’t feel safe.

Before I deleted my profile, I checked my inbox one last time. I had exchanged over 30,000 messages in the course of three weeks. I’d estimate that at that volume and at $49.95 a head, I had earned them at least $50,000 in membership fees in three weeks.

While I don’t want to disclose the name of this site for legal reasons, you can probably figure it out if you search “online ambassador dating site” on Google. And yes, this site is still very much in business – although it appears as if they may have dropped this tactic somewhere around 2009 after people started to catch wind of this particular dating site secrets and began to threaten legal action.

As for me? I guess this explains why I absolutely hate reading the messages I receive on dating sites – I typically log in, read one or two messages, and begin to panic and log out. I’m even worse when it comes to responding to messages. My mailbox on OKCupid has been at capacity for about six months now, and I haven’t responded to a single message in four or five months.

However, I did become a real community manager about eight years later, so there’s that. That being said, this is one “community management” position that I’ll be leaving off of my resume.

Oh, and fear not: I’m fairly certain karma has already bitten me in the ass for this particularly poor life decision.