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.
Read on i-D: Is Ageism Pop Culture's Final Frontier?
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?
Source-Vice.com
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