Dating Older Men: The Hustle, Reality and Support

written by Xiao mei

As the weather turns back to its blissful self, warming up and shining bright on us, I reflected on a few memories during spring and summer of last year. It was filled with happy hour vibes, cocktails on the patio, networking at political campaigns, showing up late to cookout functions and ubering from day party to day party.

During that season of fun, I remembered my dating life wasn't so boring for once. I met different personalities and mindsets when I interacted with an older age group. And my dating life, older men sort of became a fetish. It became my "thing."


For a moment, I nodded my head in agreement to liking the 70's music, I cheered with Gigondas like I was already a wino for life and cut my hair to signal an older, more sophisticated appeal. All because I gave interest dating older men. (I cut my hair to please myself first.)


How It Came About:

Several months ago I developed a strong liking in dating men between 27 to 35 years old. Why? The independence of a man who held his own was intriguing. The dynamics of conversing are intensified. I also never paid a dime. They hated seeing my wallet come out (most of the time.) But the shocking part that caught my attention, including my friends, was the major age gap.

In my early twenties, I attracted men who could play the role as my uncle. Strange things happened, but many valuable lessons occurred too.

Before you judge, hear me out because it's not so bad.

These were the most vulernable highlights I decided to share:


The Work Ethic:

If you’re not hustling, do not bother dating older men with ambition. I cannot speak for all determined 30-year-old aged men, but majority are career-focused and money-driven. It’s something they direct their energy towards after recognizing of all their victories and failures that they learned during their 20’s. With high hopes during their 30’s hopefully they’re capable to build a solid foundation for their career, wellness, and fantasy lifestyle then focus on a family.

As a direct woman, I always articulate my theory concerning the pursuit of a man’s career vs. providing space for a woman. I discovered a pattern with each man. I assumed maybe it was me and not them, but that’s bull. These men got me all the way f**cked up.

If you’re a woman who enjoys a man with power, success that incorporates multiple lines of income expect him to remain busy. That’s just facts. Yes! Support him during his career pursuit, don’t communicate 24/7 - he has work to handle, but be transparent that your time is valuable as well. If he manages his time efficiently, trust me you’ll be on his to do list. To Do.


The #1 One Word That Kills His Ego:

The #1 one word you never ever say is “Old.” Their poor ego gets shot down hearing this. Depending on the age gap this may not be the case, but old and young relationships are often looked down upon.

For dinner, we walked in the restaurant and these old, white women gave us such a dirty glare. I assumed it was because of our age difference. He assumed it was due to our different races. At the end of the day, who knows? But, if you’re going to give someone or something a try, either be fully in it or not. Reality is, others will hate so you might as well own it.


The Elongated Wait For Entry:

The best part by far is the fact older men’s control for intimate interaction is kept on lock down. Not saying they don’t want to, but patience is an essential they offer that most young men can’t. There’s no pressure. No stress. No give. No take.

Ladies, if this isn’t what you want, older men may not be for you. Because hunny they can wait.

And let that not confuse you with “you’re the one”, just understand their resilience is far more mature. (Keep in mind it’s the 21st century, so if the wait is too elongated…ask about their male history and notice if they drink tea with their pinkies up.)



Stay Chic, Stay Youthful:

Here is where I partially went wrong. I’d try speaking their lingo, hoping I’d fit in. Obviously growing up in different time periods there are hip sayings I was never educated on. A lot of woman do this subconsciously - trying to mirror a man. For example, women act interested in sports to please a man because it’s his interest. Though majority women know nothing about sports.

We say “score!” and he yells “touchdown!”

So yeah, at times I felt incompetent conversing intellectually, but I realized another thing - Older men love teaching younger chicks what they don’t know. It gives him an upper hand, makes him feel superior and dominant.


Xiao's $0.02

Although old & young relationships may not be your “thing.” Learn to be free-spirited enough to allow people with good intentions to enter your life who are capable of teaching you beneficial experiences. Your opportunities become endless when you throw away the side comments from friends and family and live for yourself.

Write down what you want in a relationship, create a mood board and place yourself in events that present those opportunities to discover.  Did I do this? No. However, I did self-reflections about why I was attracted to older men.

Naturally begin to figure out what’s best for you and all good things will come.

Thanks for reading!