Not one of the women in this article. Photo via Flickr user Phil Galdys
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. After opening the app, I realized that I had racked up dozens upon dozens of matches—many of whom were “mature” women—and it gave me an idea: I was going to try and get wined and dined by older women without leaving a date too early or dashing after I had my share of food/booze.
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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.
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The next night I set up a Craigslist posting seeking older women along with an account on a cougar dating site.
“19-year-old male going to university and working in media. 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). “I’m looking for something casual because I want to learn. 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. All of the women I went on dates with were pleasant but firm—some more so the latter. Here are the highlights.*
*All names have been changed.
That is some high-class eatin’. Photo via Flickr user w00kie
Tessa, age 39
Tessa was the first person to message me when I put my profile up, noting that she liked the forwardness I displayed in my bio and she admired how I was hard-working at such a young age. However, our digital conversation quickly turned to more shallow characteristics, such as how she my jawline was sexy and how I thought her athletic build was hot.
Since this was my first foray into the realm of dating women only slightly younger than my mom, I didn’t really know what to expect and came prepared to leave if shit got weird or uncomfortable (which I was expecting might be the case). Based on the “horror” stories I had heard from friends who had gone on dates with people much older than them, occasionally matches go awry when they find out the person is super desperate to have some kind of kinky sex or treats the younger person like a fresh crop to be harvested. I didn’t want to be corn.
When I arrived at the place—an Italian restaurant in a trendy part of town—ten minutes early, I was surprised to find Tessa already seated at the table with a napkin on her lap and purse neatly tucked beside. She looked stunning, too. In a way, she reminded me a lot of Gillian Anderson back in the X-Files days, who I had a giant crush on as a kid. That alone really motivated me to make this work.
When she saw me striding over, she didn’t stand up. Instead, she made unbreakable eye contact with me like she wanted to know my soul. Since I am a tough staring contest opponent, I kept my gaze locked as I extended my hand and made the introductions.
“How are you?” I asked, to which she replied. “Great, great. Sit down.” I followed her instructions without question and did.
One of the terms they use in the cougar community for younger guys going after older women is “cub,” and although Tessa never used it in real life, she did use it frequently in our digital communications. Of course, “cub” is essentially just a nice way of saying that a matriarch owns you, which I knew going in. I actually looked forward to the prospect of being taken care of by an older, more successful woman. It was a flip on the typical stereotypes of male-female interaction, and I like free food, so why the hell not?
After a few minutes of small talk, the ice broke quite easily. We ending up having a long dinner (€50), a bottle of wine (€20), and spent the rest of the evening walking around the city slightly intoxicated. Throughout the entire night, my expenses were covered. Tessa was an accountant and she made it clear that she wanted me to pay for absolutely nothing. I eventually made the argument that I had enough trouble letting her pay for the entirety of dinner, so she conceded and let me buy us coffee (approximately €2) when we stopped by a downtime diner.
When it came time for us to part, she became very forward with me. She came onto me very quickly, which I gave into without protest (obviously). For the first time in a long time, I actually had to do virtually nothing on my end of the equation. We kissed for a bit on a park bench and parted ways. Before I left, I told her that I’d be down to do it again, but later felt weird about it after I saw pictures of her kids—the father whom she separated from shortly after their birth—when she added me on Facebook. We never went out again, despite her sending me two messages asking to grab Baskin Robbins. As much as I love ice cream, awkward makeout sessions with someone old enough to be my parent was just a little too much at that point.
Photo via Flickr user Nicolas Alejandro
Angela, age 42
Shortly before I went on a date with Tessa, Angela reached out to my Craigslist ad with an email saying, “I’ll buy you dinner but are you dtf? Not interested otherwise.” I didn’t know how to respond, exactly. There was no photo of her, I didn’t know who she was, and the only detail she gave was her age. I mean, I usually am DTF, but I was somewhat worried about whether I was being catfished or led on by some kind of sex-thirsty predator. In the end, I sat on it for a few weeks before coming back to it while cleaning my email. After reading it over again after my date with Tessa, I figured: Fuck it, why not? With a few strokes of the keyboard, I said, “Sure. Call me.” My phone rang almost immediately.
We spoke for about ten minutes before deciding to set something up. She said we should go to a coffee shop in the east end, head to a bar later, and see where the night takes us. Once again, like the last date with Tessa, Angela would pay. During the whole process of setting up the date, I made absolutely no decisions, nor did she let me. While we were on the phone, one of things she told me was that she did not ever, under any circumstance, want me to call her a cougar. If I was to refer to her by something other than “babe,” it was to be “tigress” and I was to listen to her at all times. This kind of threw me off. I was used to being on the same level in my relationships, so it was pretty fucking weird being told that I had to submit to somebody else. For a slight moment, I kind of felt what almost every woman has felt for, like, thousands of years.
When we met up, Angela’s outfit screamed boss: She was dressed in a black leather jacket and blue jeans with tall black boots and a low-cut white shirt. She was definitely a hot-mom-type figure—kinda like a biker mom without the meth—and she was also very in control. She was so insistent on making all the decisions that, at one point in the early part of our date, she snatched my hand into a tight grip and led us to our first destination. This was an experiment and I was getting free lattes and booze, so I had little to complain about.
The entire night was mostly a blur of bar hopping, but what I do remember from it is that Angela was a very interesting woman: She told me that she got divorced from her husband—who happened to be ten years older than her—a while back, which came out of a desire to date younger men. When I asked her how many men she had gone out with before me, she said couldn’t remember but that she’d been doing it pretty regularly for the past year. She also insisted we go back to her place, to which I obliged.
When we arrived at her house—a loft near the coffee shop she originally brought us to—the whole place was set up like some kind of red-light district sex den that was built solely for the purpose of seducing me. The room flowed with creamy colors, from the gray leather couch with red velvet pillows to the white beads that hung in front of a door to the hallway. The room smelled great, too, like lavender and chocolate had a delicious baby. Neon sign fixtures with the words “Love” and other phrases that belong on Tumblr, which provided most of the light in her dark living room, were moody and dimly lit. A few candles sat burning on the kitchen table and an iPod was docked while playing some kind of atmospheric house music. It was basically like being in one of the Weeknd’s music videos, minus the drugs and mushroom-cloud hair, and I actually kind of dug it.
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As soon as I unlaced my boots and stood up, Angela pointed to me to the swagged-out couch in the middle of room. Almost immediately after my ass touched the sofa, she reached for my pants and started to rub my crotch, no kissing or small talk. I was kinda weirded out—she sort of reminded me of a friend’s aunt I used to know who drank a lot of V8 and was super-tanned. But I had also taken two Ativan earlier so my brain didn’t really give a chemical fuck about anything at this point. In a few seconds, she scooped my pants off my legs, tore my boxers off, and began to give me head immediately. I have to note, too, that this was good head. Like, the best blowjob I’ve got since I woke up fucking a mattress because I was getting a dream-level blowjob. Angela knew her game and she played it well.
Suddenly, she stopped and stood up. For a moment, I almost thought I did something wrong. Had I not fought back enough? I didn’t understand. After a pause, she pulled her pants off, and then she tried to mount me.
This is where things broke bad. When I told her I needed to grab a condom, she tried to prevent me from reaching for it. I told her I wasn’t interested in having sex without one, and she told me to stop whining. Instantly, I was no longer into it at all. Somewhat angry that I was being told by somebody what I could and couldn’t do with my own body, I dropped the submissive act and gently pushed her off. We both sort of sat on the couch for a minute while I slowly put my pants back on and explained that this had gotten too weird for me. I told her she was a very nice woman and that I was super grateful for the drinks, but that this is where it ended for me and our night of escapades.
I ended up leaving €14 on the table despite her protests not to, partly because I felt bad (even though I shouldn’t have, considering I have the right to decline sex), and partly because some deep-rooted sense of masculinity said I should have split the tab on the booze. On the stairs down from her place, I deleted our texts and her number. We never talked again. Some regrets!
Gillian Anderson. Photo via Wikipedia
Marilyn, age 40
I met Marilyn the same day she sent a message to my profile. As a real estate agent who both lived and worked in an upscale neighborhood, she had the bling to show for it. She picked me up outside of a north-end subway station around noon in a brand new Audi that smelled like fresh leather and expensive things. When I got in the car, she gave me a hug and greeted me with a big smile. She had a great laugh and was incredibly well-spoken. I was so comfortable, in fact, unlike my previous dates, it didn’t feel like I had to ease into the situation or fake small talk. She was quite fun to be around. She even liked Drake.
Marilyn was clearly into fashion. I’m talking layering and color coordination that even the most pretentious fashionistas would lose their shit over. It made me feel kind of underdressed, especially because I was in my regular greaser getup. Either way, Marilyn didn’t seem to care as much as I did. She asked where I bought the leather jacket from, to which I replied, “Some guy in the Grand Bazaar.” It was the truth and I felt no need to lie around her.
When messaging each other beforehand, we had planned to grab lunch and scope things out, to see if it was a good fit to go on further dates. I was pretty happy with that idea, especially considering she probably had as much reservations about dating a strange young man as I did dating a random older woman. We ended up choosing a cheap Thai restaurant downtown that’s popular with students in the area—somewhere I thought was busy enough that we wouldn’t be stared at.
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Marilyn and I shot the shit for almost two hours over a few plates of spicy stir fry and crunchy egg rolls. Marilyn was a vegetarian, while I’m more of a only-eat-flesh type of person, and we ended up getting into a bit of debate about the ethics of meat eating. We both agreed that animal slaughter is kind of fucked up, and she accepted my answer that I bear full responsibility for the poultry I consume on a daily basis. She ended the conversation by making a quip that she “eats meat… sometimes.” On that note, I ordered the bill. We split it without argument. It actually felt quite normal.
After food, we parted ways and made vague plans to meet up again. It wouldn’t be until the end of the summer that we did actually meet up for coffee. When I ran into her this time, things were quite different. She seemed to be a little less on edge but a little more drained. Her energy was lower, she wasn’t smiling as much, and she seemed to be there out of a show of courtesy rather than to actually have fun. When I asked her how things were, she told me that her mother passed away recently and things have been rough.
We spent the rest of the evening talking and walking around the city. It was a bit of a gloomy day, both because of the rainy weather and our conversation, and we ended up at a church. It was heavy. Marilyn told me that she needed some time to herself, so I gave her a hug and we parted ways. While we never ended up meeting again, I texted her to check up on her and she said she’s doing much better. She also told me that she wants to meet up soon to grab more Thai food. I told her I was totally down, even if that was a bit of a lie in order to stop her from feeling any worse than she already was from her mom dying.
Vanessa, age 48
The final woman, Vanessa, contacted me through my Craigslist ad before I pulled it down—which I did after realizing that school was coming up and I shouldn’t keep going on dates with women twice my age when I would be surrounded by thousands of university girls in just a few weeks.
Vanessa messaged me with a very detailed and highly specific profile of herself. Aside from her height, weight, and hair color, she also emphasized that she was of Chinese descent. When I emailed her back saying that I was interested, I also asked her why she specified her race. She told me that some men had told her to essentially fuck off once they met in person when they realized she was Asian.
As a guy who grew up around bro culture, this was depressing but unsurprising to me. Men, especially white dudes, can be absurdly offensive with their “fetishes” and choices in women. Regardless, I assured her that I legitimately did not care and that anyone who did that to her was a raging asshole. We set up a date for the day after at a Korean BBQ restaurant with plans to go and do a photo shoot by the waterfront later. (I happen to do photography and it happens to be a very useful icebreaker on dates, OK,? Please don’t judge.)
When we got to the BBQ and ordered our food, I had a hard time communicating with her and it was kind of pissing me off. She spent a lot of time on her phone (it’s not just a millennial thing!) and kept giving me very vague responses to my questions. Thankfully, since a Korean BBQ requires actual, y’know, real-life engagement to cook your own food and eventually eat it, she did put down her phone occasionally to throw some beef on the grill and talk to me for a minute. Strangely, every time we talked, her eyes would dart around the room, never staying locked with mine for too long (not like Tessa!), and she seemed genuinely nervous. I tried to appear as relaxed as possible to make her feel more comfortable, even depressing my posture and making my voice sound soft and angelic like a social worker does, although it was to no avail. She was not easing up.
After we left the restaurant and started walking toward the waterfront as planned, she kept checking her phone, even more frequently than before. About halfway there, I stopped and asked her if she felt OK, at which point she broke me the news: Her husband (whom I didn’t know existed) was asking her where she was and had suspected she was cheating on him.
Taken aback, I asked her why she didn’t tell me in the first place, and she said it was because she was afraid I might not go on the date with her. Of course, she was right—I definitely wouldn’t have gone on a date with somebody who was not only cheating on their husband but also putting me in potential danger of being at the other end of her partner’s wrath—but I was having trouble actually giving her the whole truth considering how anxiety-ridden she already was and how she might’ve ended up crying in the middle of the busy street we were now about to argue in.
Instead, I told her that I found it a little bit weird and that we should pack up the date so she can go see her husband. As I learned, that was the wrong fucking choice. Vanessa blew up on me, accusing me of being shortsighted and inconsiderate of her situation. Her voice began to grow from “I can’t believe you just said that” to “People are going to start staring at us with great concern really soon.”
After going off for about half-a-minute, she stopped and told me that she would put her phone away from the rest of the date if I would put the whole thing behind me. At this point, I was totally uninterested and ready to decline her offer, so I just kind of stared, shook my head, and sighed. I told her that I’d be glad to walk her back to her car, but that I really saw no point in continuing this anymore. She told me that she would be fine and called an Uber. Seeing this as my chance to eject the fuck out, I nodded, said goodbye and popped in my headphones for a long and relieving walk home to some Phil Collins. You can judge me for that.
What I Learned
If there’s anything I pulled out of the entirety of this experience, it’s that dating people way older than you is a delicate balance between challengingly exciting and really fucking uncomfortable. While it’s hella awesome to have expensive dinners paid for you, someone to lead you around, and to have sex thrown at your dick, I still couldn’t fully stomach the concept that the women who were providing me with all these luxuries were looking at me as freshly-legal ass.
Frankly, in terms of the actual dates themselves, I’m still undecided on whether I’m just an immature piece of shit or that some of the more cringe-worthy moments were genuinely not my fault. For example, while I found Angela’s insistence on dominating me completely off-putting, you could also make the argument that I just wasn’t being open-minded enough, especially considering I was supposed to be assuming the role of a sugar mama’s cub. With that said, I have a hard enough time watching porn where dudes yell obscenities at the women they’re fucking, and the one time an ex asked me to choke her during sex, I actually went half limp. I guess I’m just a softie.
But would I recommend getting sugar momma’d to other dude my age? Yes. Yes, I would. Not because I can guarantee they’ll be happy with the outcome—they might leave as weirded out as I was, especially after I realized how unlike porn it actually was—but I am a firm believer in learning things the hard way. In fact, I think the only thing to truly know if something’s right for you is to try it, fuck it up, and then audibly make small whimpers when you relive the terrible moments of your experience over, and over, and over again (this may or not be something I actually do). Also, you’ll get to kick it for a bit and get drunk for free instead of splitting the tab like most culturally-appropriate people do nowadays. How can you pass that up?
