I have a love/hate relationship with Craigslist, the American noticeboard with sections devoted to job, property, services and dating. I love, well, its randomness, the way it always manages to turn up someone somewhere who can quash a bug on my website or make my PowerPoint presentations shine. I hate how finding those people often means having to wade through the dozens of imposters, con artists and fantasists who use the site. Still I am loyal; at least from time to time.
Recently I did use it for something mutually beneficial. While searching for an interior designer who wouldn’t cost me an arm and a leg, I discovered one who refused to charge me on the understanding she could showcase the work as a way of achieving her British Institute of Interior Design qualification.
And then there’s the sex stuff – mutually beneficial but for different reasons altogether.
Eight years ago, before Tinder arrived on the scene and stole some of Craigslist’s thunder, Craigslist was an easy way to find local travel guides with special ‘perks’. I was in my mid-forties at the time, visiting Rome. I encountered one very nice young man who travelled all the way from Naples to Rome to meet me and show me around the city. He arrived, took me for a walk around the Coliseum and then, in my 5-star hotel room, he performed his final generoso—making me squirt all over the 400-thread count Egyptian cotton sheets. Craigslist had its purpose back then, it made business trips more fun.
Given my happy history with Craigslist, on the first day of spring, when the sun was shining brightly, the daffodils were in bloom and even complete strangers smiled at me while shopping on Kilburn High Road, I decided to throw the dice and post a personal on Craigslist. I was horny and was hoping to find, if not a partner, at the very least a shag.
Having just attended a workshop at the UK Dating Fair the weekend previously, entitled “Who Am I Compatible With?” a class that encouraged us to seek partners with shared values (apparently, it’s a myth that opposites attract), I was inspired to make my desire clear from the start:
Dominant, tall, slim man (45+) sought by confident, attractive woman.
I listed the attributes I was seeking: someone older, wiser, perhaps semi-retired, a lover of good food and wine and travel. I mentioned that I generally identified as submissive but leaned towards being a take-charge person in my day-to-day life. I specified no toy boys or married men, knowing from past experience, on Craigslist at least, that many men tended to skip the ad’s text and go straight to the image. I’d posted “no one under 40” and within five minutes received dozens of messages from Millennials telling me I was the perfect vehicle for their MILF fantasy.
In my ad, I requested that the man have all his own teeth and was able to write in full sentences, and I made a point of noting that I preferred men who looked after their bodies. “Most importantly,” I added, “you do not take yourself too seriously, are naturally curious about the world and interested in what others have to say.”
I pressed submit and, as has been my experience in the past on this site, within a few minutes the replies came flooding in.
There were the usual rejectees: men who couldn’t spell or who used text speak, recent college grads my own sons’ ages, and guys who provided a cock shot, a phone number, and nothing else. However, there were also half a dozen that stood out. They included a 45-year-old firefighter who claimed to be in ‘good shape.’ I was suspicious, given my CL experience with men and knowing that “good shape” was a subjective term. Another was a 39-year-old banker based in Canary Wharf with a penchant for poker and a ‘mature city professional,’ who apparently thought that information alone was enough to entice me. And there was a man named Bryan, a 47-year-old Canadian based in London, who sent me lots of pictures of his erect penis. It was of a pleasing size and shape, although I’ve always preferred a man who keeps it in his pants until after a face-to-face meeting, after which making a penile appearance is the logical next step.
After skimming through another ten or twenty messages, one arrived that contained the four magic words guaranteed to make me wet. Semi-Retired. Investment. Banker. That is – a man with money and time on his hands. I’m not a gold digger but I’ve funded most of my relationships and no longer have an interest in doing so.
The banker’s name was John and he had a double-barrelled surname which indicated Eastern European origins. A quick Google search revealed a slightly dodgy past. He’d had some kind of run-in with the FCA over an investment scheme that hadn’t gone well, and been suspended by his employer, one of the larger banks. But then, is that really unusual in that business? Over the years, I’d read numerous stories in the broadsheets about bankers cooking the books or setting up dubious trust funds or Ponzi schemes. At least John hadn’t gone to prison. He seemed interesting, at least, and probably had a story to tell. I got in touch.
John told me he spent most of his time managing a block of studio apartments he owned in West London and one he had just purchased in Leipzig, his hometown. He had a nice voice, sounded friendly and relatively interesting.
We met on a Sunday afternoon, at a Hilton Hotel bar, at John’s suggestion.
I got there early and took a seat at the back of the room, away from the handful of other customers scattered around the cavernous space. Dissonant jazz music was playing through the speakers. The décor looked like it had been lifted from a Bond movie —dark brown wallpaper, long mirrors, large high-backed 60s-style chairs. The bar was twenty feet long and its stools were deserted. I ordered a glass of Malbec, handed my card to the waitress, and hoped I wouldn’t be drinking alone. Having been stood up on dates with Craigslist prospects before, I’ve learned that one man’s “I’ll be there” is another’s “Sure, unless a better opportunity arises.”
John arrived 10 minutes later, in a mix of brown tweed jacket, purple flowery shirt, a pair of jeans and a grey flat cap—country gentlemen, by way of Bayswater. His skin was almost transparent and so white it made him appear otherworldly. Slim and about six feet tall, he took off his hat to reveal a shiny, bald pate. He had small blue eyes and slightly lopsided lips that I felt drawn to because their asymmetry was surprisingly fetching.
I was in no position to judge him, as I was wearing jeans, tan suede cowboy boots and a multicoloured trilby, which covered my long hair, recently tinted fuchsia, my nod to difference.
I stood up to kiss him on both cheeks. “You made it,” I said, the surprise barely hidden in my voice.
“Well, of course,” he replied, sincerely.
John called the waitress over and asked her whether she had any non-alcoholic cocktails. Red Flag number #1. It was late afternoon and I knew John had taken public transport. A drink or two usually takes the edge off first meetings. It looked like I’d be drinking alone. By the time, his non-alcoholic mojito appeared, I had almost finished with my wine and ordered another, not caring whether that might bother a non-drinker.
We discovered a shared interest in property, as I’d recently renovated my home. He told me about his property portfolio and a renovation project he had been working on in a remote Eastern European city, now almost complete. After an hour we were still talking about it. He took out his phone and we went through the slide show of images on it: the newly tiled bathroom, the dining table shipped from Italy, the balcony and roof terrace. Like so many other men I’d met online, the focus of the conversation was him. What he was doing, his own achievements, what he enjoyed. And I put up with it because I was ambivalent. And horny. And he was sufficiently intriguing.
“Maybe you can help me christen the bed,” he said, confidently. I laughed nervously, despite myself and despite my experience with Craigslist men. I hadn’t even had a sip of my second drink and he was already steering the conversation towards sex. “And you can give me some decorating advice too,” he added.
I wasn’t sure I wanted to fuck him or be his interior designer. Still, he ticked many of the qualities I was looking for in a potential partner. He was a semi-retired. As a former investment banker, he was solvent. We shared many interests. While he wasn’t traditionally good looking, he could hold a conversation, although laughter was in short supply. He confessed to voting for Nigel Farage and I wondered if I could overlook that. I wasn’t sure I could. That would be hard to explain to my friends, who were rooting for Jeremy Corbyn at the time. I was horny, so I tried to remain open-minded. We had met on Craigslist, after all, not Guardian Soulmates or one of the staid sites targeting those seeking long-term relationships.
We ended up taking the Jubilee Line together. As we entered London Bridge station, John turned around on the escalator, pulled me towards him and pressed his lips against mine. His tongue probed my mouth. I was a little merry with the drink so I let him for a few seconds. Then I pulled away.
“Come back with me,” he said. I told him I had to work the next day and get up early, which was half true. By this point, I just wanted him to go.
We got into the carriage, while I counted the stops until he got off at Baker Street. I didn’t want to go home with him. I wasn’t even sure I wanted to see him again. I was desperate for him to say something funny, to break the awkward silences, the uncomfortable conversations about sex and the misplaced intimacy.
When I got home, I went to my computer and saw another 40 emails in my inbox, all of them responses to my original Craigslist post. I deleted them all. And then I pulled up the ad and pressed delete. Craigslist had once been a reliable site for connecting with men, back when I thought of men as items on a takeaway menu: to be selected, delivered, nibbled on, then tossed aside. Craigslist still worked that way: it brought me a wide selection of prospects and then face-to-face with John, a man who found me attractive and wanted a shag. Just hours earlier, I’d thought I’d wanted the same, and when given the opportunity, I’d opted out.
Special thanks to Mark Rathmell for creating the illustrations.