The first job I ever had in my adult life was boring as shit. In my early 20s, I decided that my future career would be in the wild world of marketing, so I got a job doing SEO and writing copy for a Canadian company worth billions of dollars. Their money came from providing a specific type of software to very niche industries for tens of thousands of dollars. The job was lucrative, but frustratingly tedious. To break up the monotony, I would often take small breaks and walk around the office, getting acquainted with the flurry of executives who populated the sprawling workspace.
One of the executives, whose office I wandered into one day, worked in sales. I'll call him "Tim." After some time, the conversation between us turned to one of the three most popular subjects in office life: women, sports, and weather. Tim confided that he was having trouble in the romance department, and how difficult it was for him to meet potential partners since he worked almost constantly. Since he was in his late 40s, Tim was out of touch with the internet and the solutions it afforded men like him. He had never heard of online dating, and was hesitant about the idea of meeting strangers off the internet. He still thought of the process as similar to answering an ad in a newspaper, where he would have to read a block of text a person posted online and then correspond with the anonymous stranger until they agreed to meet in real life with the hopes that neither of them was grossly disfigured or a psychopath.
Tim had never heard of OkCupid, the free online dating site that matched you with potential dates based on your answer to fun personality quizzes. I explained the concept to him, and while he was interested, he said that this sounded like too much to manage in addition to all of his important business work. A lightbulb went off inside my head: I told Tim that I had a solution, offering to act as his own personal, online Cyrano de Bergerac.
We agreed that I would create and run his account, corresponding with whichever women we managed to charm, and setting up the dates for him. I would act as a sort of personal assistant, scheduling his nights in his calendar and providing what was essentially a cue card with all the most pertinent information: like where these women worked, what they did for fun, and a few random facts for him to sprinkle through the conversation so it would look like he was paying attention to their online banter. We agreed on a standard rate for each plateau he achieved with a date: I'd received $25 for every completed date, $100 if they ended up having sex, $200 if it led to a real relationship, $5,000 for an engagement, and $10,000 for marriage.
Tim was not attractive by any means. His nickname around the office was Shrek, and it was one that he embraced regularly. He was short, bald, lumpy, and didn't know how to dress. The task of creating an online profile for him was gargantuan, so the only possible solution I could come up with was to frame the focus in the truth: He had a lot of money, and not a lot of time. He was a very important man who didn't have time for a social life, and was now looking for someone to share his time and riches with. I must have used the word "executive" over a dozen times in his profile. After a few hours of writing and re-writing and uploading the only three pictures that existed of Tim in a suit, the profile was complete.
Anyone who has used OkCupid knows that the brunt of your success hinges on how compatible your score is with the other party. Your score is calculated as a result of personality quizzes that suss out your true intentions and character traits. I completed this as best I could, using the knowledge I gleaned from conversations I had with Tim and what I observed him doing in the office. I knew that he was looking for a long-term relationship (that would hopefully, for my sake, result in marriage) and that he was allergic to most pets, because those things came up in conversation.
I answered the questions to reflect that he was spiritual but pragmatic, a Jewish Kabbalah practitioner who still believed in cold-calling at random to sell thousands of dollars in software. He was charitable but reserved, something that I observed when he would come into the office on random days with breakfast for the staff of 50 before retreating into his office, not to be seen again until five o'clock when he waved goodbye for the night. Slowly, I pieced together a comprehensive portrait of a man who I had spoken with for less than an hour in a professional setting.
It was easier than I expected to successfully start conversations with women online as Tim. Although he was objectively cosmetically challenged, women seemed to respect the fact that he was looking for something serious and was ready to settle down. Most of the women were in their late 30s and were receptive to Tim's purposefully corny messages, and the majority of women who engaged with Tim online accepted Tim's request for a date within five to six back and forth messages. After the first day, Tim's calendar had four appointments spanning the rest of the week and the weekend.
The first date was apparently terrible. She was a substitute teacher who was looking for someone to help her parent her six-year-old, a fact that I mistakenly forgot to ask about and include in Tim's notes. He wasn't happy, giving me an earful when he called me at 10 PM after he dropped her off at home. The second date went better: They went out for an expensive steak dinner and visited a strip club to get each other lapdances before going home separately. Tim had fun, but it was apparent that she had simply used him and his American Express for a night out. The third date proved to be the best one. She was an art collector in her early 40s who turned out to own a sex swing in her downtown condominium, a fact that Tim regaled to me as he proudly filled me in on Monday morning.
Eventually, I would go on to get another job, but when I met with Tim two years later, he told me the good news. He had apparently gotten engaged with Ms. Sex Swing, and would be tying the knot the following year. I congratulated him and casually reminded him about the deal we had made almost three years prior. Red-faced at his forgetfulness, Tim apologized and wrote me a check for $5,000 on the spot, proving that I managed to get the "charitable" part right when it came to those quizzes. The marriage never ended up happening for reasons that are unknown to me, but as far as I see it, it's for the best. If Tim could go on to get engaged at least two more times before finally getting married, I might be able to afford a down payment for a downtown condominium of my own, albeit without a sex swing.
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