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Swearing-Off Men Over 30

Hearing a man say he's 30+ fires off the same synapses for me as when he says he's an Aries:


I rarely get approached by men my age, and I used to think that was a good thing. People fill your head with the idea that older men are the diamonds of the dating pool: more financially stable, hoe/player phase out of their system, raised with old-school morals and know how to treat a lady. But while some of those things trend true, they come at the cost of the curiously intrinsic tension between the old and the new.

Being part of the Millennial/Gen Z generational cusp positions my mindset at a unique intersection of modern inclinations and traditional ideals. I find younger men to be more relatable than their older counterparts, not because it's so impossible to find things in common when navigating an age gap, but because they share more of the cultural sensibilities that play a role in my general outlook and personal value system.

Things are changing. The world is more inclusive and more attentive. Defining the bounds of not enough, just enough, and too much when it comes to keeping things PC might be an impossible task, but finding a partner with a compatible eQ proves more challenging when searching amongst men who came of age in times where sexual harassment was normal, nobody went to therapy, and everyone was still tossing around sayings like "no homo."


The other side to that is the sometimes predatory nature of age gap relationships. I'd be curious to discuss how this plays out in relationships between older women and younger men, but my experience permits me to speak only upon the opposite.

Youth and desirability are so inextricably linked in the context of womanhood as defined by the male gaze that we don't always stop to think about why that is. Archetypes like the innocent school girl are far more favorable to the bitter spinster: a young girl is eager to please while an older woman is too set in her ways. Rigid, conceited, and difficult to deal with. Obviously still single because there's something wrong with her.

In these cases, age and maturity can be easily conflated. I think it happens to be a coincidence that women and girls are so conditioned to be polite and agreeable that it often takes a second coming-of-age period to learn how to set boundaries and distinguish between self-care and selfishness; and perhaps that's why women of a certain age aren't checking for certain men, who then have to resort to dating young. Many men assuage the suspicions of younger women still navigating this stage by telling them how mature they are "for their age" - a flattery tactic that creates a false sense of security and specialness and masks any kind of maliciousness or manipulation.

It's only now, growing older, that I can look back at my 18-year-old self and her 28-year-old partner, my 19-year-old self with a 24-year-old, or even more recently at my 23-year-old self with a 33-year-old and see red flag power dynamics at play that just didn't really make sense when you think about how equally-yoked partnerships are supposed to play out.

(TW: SA) Dating Grant Williams (click to expand/collapse story)

That 33-year-old, let’s call him Grant.

We met one day when I was at work - he came in with a friend at sat at my bar. After some banter and conversation, we exchanged information and agreed to see each other again.

I enjoyed things between us at first. He would always call me “princess” and make me pancakes in the mornings. But soon, I started to notice tendencies that made our interactions more uncomfortable.

He neglected to mention when we first met that he was still finalizing a divorce. He spoke of his ex-wife with an overwhelming eerie disdain; spoke of his child with a strange bitterness. After a casual meeting with my mother, he would constantly make jokes about how beautiful she was. How he was just using me to get to her. And when I confided in him about my PTSD and history with sexual assault, he took it upon himself to push my sexual boundaries with his own forms of shock therapy.

One thing I was adamantly opposed to was anal sex. On this particular day, that was the only thing he wanted. After breakfast, I remember sitting on the couch in his living room when he started making advances. The more I told him I wasn’t interested, the more aggressive he became. We eventually started wrestling noisily as he pinned me to the floor grunting the words “don’t make me take it” over and over again. There was so much commotion, I started to worry that the people downstairs would get suspicious of what was going on - he owned and operated a gym from his basement and there were people there at the time who I was sure could hear everything. Just as I decided to stop resisting, something must of come over him to realize that I was unhappy. He stopped, and I went to the bedroom to sleep.

Once I woke up, we argued about something unrelated. He dropped me off at my mother’s work office, and made an off-color joke about how he liked the way she looked in the dress she was wearing. When I told him for the ump-teenth time that I didn’t like his aggression or crude sense of humor, he responded by telling me that he was no longer interested in talking to me.

I was so shocked and infuriated by the sarcasm and backwardness of all this, I didn’t know what to do.

He reached out to me later after more than a month without communication and said, “You miss Daddy yet?”

It should go without saying that I don’t think this experience is a representation of anyone other than this one individual, but I often think back to everything that happened between us and what I learned about power play. I trusted Grant implicitly because of how grown he was. But by doing that, I ignored glaring character flaws that ultimately exacerbated my trauma experience.


They tell you girls mature faster than boys to justify the regularity of age mismatches, but at a certain point the buck has to stop. When I tell people how abnormal it is for me to be approached by men my age in a serious manner, they always talk about how intimidated people must be by my success or intelligence. Yet I always felt "cool" to be so young with partners who were so much older. Shoe on the other foot, I wouldn't even typically consider a younger man as a dating prospect, but maybe that says even more about my social conditioning. I remember starting college with the mindset that I'd better enjoy my freshman year as much as possible because my dating pool would only shrink further and further the farther I got into my academic career: a freshman girl with a junior or senior? Great! But a senior girl with a freshman guy would just be...creepy. Where does that double standard really come from?

What have your experiences been with older partners? With younger ones? How do you think gender roles influence age gap dynamics?

Let this be a reminder to trust your gut! Partnerships of any kind require the right sort of balance. Know yourself. What you like and don't like isn't something that has to be explained or justified, and your instincts will lead you towards the right person (and away from the wrong one!).

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