4 Real Men Talk About What It Was Like To Date An Older Lady

There is just something about people with huge age gaps who happen to be in relationships that just captivates most of society. And it’s usually the “older man – younger woman” dynamic or narrative that a lot of people have a tendency to obsess over. They make jokes about how the man probably has a lot of money or that the woman must have a bunch of daddy issues. But people rarely ever give as much attention to the “younger man – older woman” setup in a relationship. And it’s a really different set of dynamics with this kind of relationship. If you’re curious about what it’s like to be a younger man who is dating an older woman, then here are a few stories from some real-life men that might seek to enlighten you.

1. Jake got really tired of all the “mom” jokes.

“I happened to be in an intimate relationship with someone who was twice my age. I was only 25 at the time and she was 50. She had just endured being in a terribly toxic and manipulative marriage with a psycho. She also had 3 full-grown children with two of them actually being older than I was. They all treated her terribly. Her ex-husband was milking everything that he could out of the divorce with her. And her kids barely ever talked to her. She felt so lonely and vulnerable. She felt so insecure and unlovable. They walked all over her and she just allowed them to do so. We tried to make things work between us despite all the chatter and noise surrounding our relationship. We were running a successful business together as a couple. We were able to afford a nice home and a fancy car too. I had a really good life with her except for one thing: I just wasn’t happy. I didn’t feel happy anymore. I didn’t feel fulfilled in our relationship. That’s when I realized that age isn’t just something that you can choose to overlook after all. It’s really something that generates huge differences in a relationship. I was getting so tired of the mom jokes that everyone was hurling my way. And I never felt comfortable with the fact that she had kids who were older than me. I hated the fact that they existed but she still loved them because they were her kids. We first got together and the sex was amazing. But then she reached menopause and she started to have  a growing disinterest in sex. That proved to be too problematic considering that I was a 30-year-old man with a lot of needs. I realized that I would be miserable if I didn’t choose to just get up and leave. It was really difficult to do but I decided to talk to her and end things. It was hard on the both of us. But I know that it was something I really had to do.”

2. Henry just loves the sex.

“I’m in a relationship with someone who is 9 years my senior. And of course, the blaring differences between us are financial and professional in nature. She is way more ahead in both respects than I am. She has a really solid job and she is making way more money. I’m still struggling to try to climb my career ladder and she seems to have found a lot of stability in her life. But there’s one thing that I loved about her right off the bat: she is absolutely amazing in bed. The thing about her is that she’s experienced. She knows what she wants and she knows how to get there. And that makes my job a whole lot easier. She just tells me what to do and I execute it. The sex is always amazing. It’s just annoying how sometimes, she expects me to have everything together in my life even though I’m so much younger than she is.”

3. Gerard thinks that he’s still the more mature one in the relationship.

“Frankly enough, I feel like we are in a very normal relationship even though she’s a decade older than me. She’s still really immature and naïve. I find myself having to put her in her place a lot of the time. Also, I’m the one who seems to be adding a lot of structure and order to our relationship as well. It’s no different than dating a girl who would be much younger than I am right now.”

4. Frank loves the lack of drama.

“I just love the fact that older women are so over the drama. Younger girls tend to attract and draw drama into the relationship. I don’t like that. With her, seeing that she’s 8 years older than me, she’s seen it all. She has been through the ropes and she knows how exhausting drama can be. She doesn’t want any of it anymore and I get to reap all of the benefits.”

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