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‘I Dated A Woman 10 Years Older Than Me’

Stop with the MILF jokes—these guys give you a peek into the ups (and possible downs) of going for someone more mature
by Cheekie Albay | Jul 14, 2018
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Men love young women—ain’t no rocket science to it. But to some men, the allure of the confident, self-assured older woman is strong enough to make them break away from the convention of worshipping college girls. And it’s not just some Mrs. Robinsons fetish—these men have found in these worldly women not just a great bedroom buddy, but a person to learn from, in more ways than one.

Here, two men tell us what it’s really like to date a woman leagues ahead in age and in wisdom. From a young man forging an unexpected bond over the space of a few continents to another coming to terms with his faults after failing at three May-December flings, see what can happen when you make that connection—minus the Stifler’s Mom clichés.

“I think our shared interest in many things was the main reason we never found any issue with our age difference.” – Marky Ramone Go, 36,

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I was 24 when I met Naomi* on She was a Filipina based in Chicago and almost ten years older than me. We got along through common interests in music and books and shared a common proclivity for the Beat Generation in particular.

From online interactions and long chats over Yahoo! Messenger, the day came when she came back to the Philippines for a visit. We scheduled a meet-up at SM Megamall. I never expected anything out of it; I assumed it would be a one-time thing. An “eyeball”—what online people then called it. But the moment we met and sat down inside a coffee house, I instantly felt a unique connection. As someone who speaks a few words, especially with people I’ve just met, I surprised myself by letting out an endless stream of words from my mouth, followed by bursts of laughter from her.

One night as I was reading the book she gave me, Lawrence Ferlinghetti’s A Coney Island of the Mind, I received a text from her inviting me to watch a film at the French film festival then happening at Shangri-La Plaza. I jumped from my bed and said yes at once.

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Over the course of the few months she was here, we would always meet up to just hang out. We’d meet at random cafes and talk about books, films nobody I knew had seen, and music. I think our shared interest in many things was the main reason we never found any issue with our age difference. Soon, what started as mere friendly dates became an intimate relationship.

When she flew back to the States, things kind of mellowed down between us. In the succeeding years, she settled into a steady relationship with a man who I believe is the same age as she is.

I still think about her once in a while. Each time I come across the film The Reader on cable, I remember the wonderful memories we shared together. If there’s a culprit behind why things never worked out between us, I guess it would be the physical distance that separates us. Not the gap in age.

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“I was intrigued by the way they thought and I was curious about what they knew. They were ahead of me in life and I wanted to know what was up ahead.” –Noel, 39

With all the women I’ve dated, it’s always been about the interesting conversations. But for the older women in particular who I dated in my 20s, I was intrigued by the way they thought and I was curious about what they knew. They were ahead of me in life and I wanted to know what was up ahead.

Jen* was a lawyer, ten years older than me. She was over the whole “gimik” thing, and I loved that she and her friends went out to relax and actually talk—really catch up and exchange ideas. When we had been dating and acting like a couple for a while, she began dropping hints about putting a label on the relationship. I tried to act cool, but deep inside, I freaked out. It wasn’t that I wanted to date other people; I just really didn’t know what I wanted in my life, let alone who I would commit to. I started fading away, then we had “that talk,” and I feebly said something along the lines of “I’ll think about it.”

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Petra* was the youngest older woman I dated at a five-year age gap, and she was the only one with a kid. I was really interested in the way she thought, and she seemed to like me, too. But then there was “that talk” again. She wanted to know if I was committed enough to her to be introduced to her daughter, which she was careful about. Like with Jen, it was too much, too soon for me. I could barely take care of myself, let alone a kid. I wasn’t ready to be a dad.

I met Brenda*, again 10 years older than me, at a convention. We had the same interests, she had a nice smile, and we naturally gravitated toward each other. This time, I was the one who initiated “the talk.” She had her doubts—she was the only one among them who expressed concerns about the age difference—but I was really into her, so I just went for it.

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I really liked Brenda. There was something comforting about being with her—I hate to use the word “motherly,” but for lack of a better term, it was really nice feeling like I could be myself running around like a headless chicken and she would still be there for me. But after a while, little things started to get to me—I found her too conservative, for one—and I broke up with her.

I don’t think it was just physical attraction that I felt for them. The fact that they were open to me was attractive, considering their status in life, and that made me feel special. But later, I’d feel insecure about not having achieved the same level of career success or status in life, and I’d realize I was being a mental and emotional parasite. And, being the younger one between us, there was always a way out for me. My age and lower status in life allowed me to keep the back door open for an exit.

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Looking back on these relationships now, I feel like a jerk. But then again, I don’t think I really knew any better. I never really had a father figure to help me develop self-confidence, and since my mom was overbearing, I was used to someone else taking care of me. I’m grateful these women were in my life, and I regret having used them and hurt them, but I’m deeply sorry and didn’t really mean to cause any harm.

With these women, I thought I could learn a thing or two about life and fast-forward my growth, only to find out and be disappointed that growing up actually took a lot of work, work that I couldn’t—and shouldn’t—pass on to someone else.

*Names have been changed

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