Fed up of having bad luck with his profile on dating sites, 36-year-old Sy Thomas of London went through an entire makeover: feminine clothing, makeup and a full wig. He wanted to pose as a woman and did just that: to his surprise, getting 400 messages within the space of three days. The messages weren’t all that positive, either: some were downright sleazy.

Reason for Posing as a Woman

Sy explained in experiment in a video with more than 200,000 views. He said: “I'm a single man growing increasingly frustrated with online dating. It got me thinking what if I was a woman. Maybe I'd learn techniques from the men trying to woo me.” The makeover was filmed and posted on the WhatIf? Channel. Part of his getup included fitting chicken fillets into a strapless bra.

Makeover: From Sy to Simone

After shaving very closely, Sy put on a lacy black dress (tight, of course!), did his eyebrows and applied smoky eye makeup as well as bright pink lipstick. When the transformation was finally over, selfie-taking began. He decided to change his name to Simone and state his age as 28: the sort of individual who would deign to take selfies whilst holding a coffee cup outside. The experiment, to his surprise, was certainly a success. He said: "I have been inundated with responses, it turns out I'm much more popular as a woman." "Look, it just goes on and on," he said, showing the matches he'd received. "I've been on the dating apps for years and I've never had as many as I've had in days."

The Messages Start Pouring In

A lot of messages on the site began with a simple "hello" or "hi". However, more interesting ones were soon to come. Overall, Sy was wholly unimpressed by the openers that he received. Sy has now urged men to put a bit more thought into what they send. One seemingly harmless message soon turned crude:

"Do you like Harry Potter?" it started. The reply: "Very much." The message then continued: "If so you should open up your Chamber of Secrets and let my Basilisk Slytherin." Steamy messages continued: "If you were a washing machine, I'd put my dirty load inside you."

"I need a massage," a rather direct individual messaged. Another one was simply more complimentary than anything else, with "Damn girl!" and accompanied with a winking face. Another posted: "Are you a cigarette? Because you’re smoking hot and I want to stick your butt in my mouth." Despite the heaps of filth that Sy received, there was one hopeful message: "Your eyes are amazing. Nice to meet you."

According to Sy, "He's correct, they are spectacular." There was of course a message that went along the lines of an insult more than anything else, "You look like trash." Charm offensive was of course also on the menu when Simone received, "And I thought owning a model agency and a nightclub I knew what sexy women looked like."

"I clearly didn't, until now."

"Down with the kids" is something that Sy is not. One sender shot a "WUU2" message. After discovering that it meant "What are you up to?" Sy said, "I was inundated, turns out I'm very popular as a woman.

"But what have I learned from these opening messages for my own experiences online?

"A lot of these opening messages, you'd never say that to someone in a bar.

"The best messages were the ones that were genuine and nice and those were the ones that hit home and that's what I'm going to be more like when I'm doing online dating."