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I was lying in bed this past summer when I had the sudden urge to try something new. After reinstalling Tinder on my phone—which I removed after ruining most of my matches by spamming them with Drake lyrics—and setting up my profile, I was prompted with a choice: What was the age range of women I was interested in? With a nonchalant slide to the right, I set the end zone at 50 and began swiping away.
Eventually, I got bored, my thumb got tired, and I drifted off to sleep. The next morning, I woke up to a rumble, and another rumble, and another rumble. The prospect of dating a hot, mom-type figure is the fantasy of most straight guys growing up, but getting sugar momma’d is something a little different. Giving up the reins and showing some vulnerability as a man filled with machismo is a step beyond just beating off to a video under the MILF category on Pornhub. This was full-on commitment to a different lifestyle and way of being treated.
It’s an experiment I needed to try to know if the real thing lived up to the hype. The next night I set up a Craigslist posting seeking older women along with an account on a cougar dating site. I’m a pretty open book and I’m down for just about anything,” I wrote in my bio, following up with some details about my appearance not hideous and my financial status terrible. Don’t expect anything long-term, but don’t expect a quick hit-and-run.
With a partially-blacked out shot of my face for a profile picture, I opened my account and left it open to the public. For the following month, I would go on multiple dates with women from the ages of 35—48 in Toronto.
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