Thought Catalog
March 21, 2014

10 Things I’ve Learned From Dating Rich, Older Men

Report This Article
What is the issue?
New Girl: Season 2
New Girl: Season 2

I love older men. I always have. My first crush was my dad’s best friend. As I got older I lusted after my high school teachers. In college I’ve done my best to seduce professors (I can’t claim to be a minx, since I’m still waiting on this one to work out).  I’m attracted to authority, money, and intelligence. Since entering my twenties I have had natural chemistry with men in their late thirties to early forties. These men are successful, attractive, and rich. I’ve spent the past year living out my secret desire to date older men. This is some of what I’ve learned:

1. Marriage doesn’t mean half as much of what you thought it would when you were younger. Being party to an extramarital affair just shows you how easy it is for anyone to do it. Marriage is boring and gets old for most people. I’m not saying that a genuine partnership predicated on commitment and honesty isn’t possible, or valuable. Generally though, most people don’t uphold the virtue of fidelity and the partnership that comes with that.

2. There is something unbelievably hot about a good dad.

3. There is something fascinating about a person who has seen the world, experienced more than you, is financially stable, and already knows who they are.

4. There is very little to fear from the unexpected when dating someone twice your age. You already know their behavioral patterns and how they will respond to the major stress situations like children, fighting, and getting serious. It’s almost comforting. Even if I don’t like what I can reasonably expect to happen. At least I know what that will be and am (mostly) emotionally prepared for it. They also don’t care to deal with drama or play games. Their standards are higher for what they are willing to put up with when it comes to emotional maturity. I know they exist, but I’ve yet to date an older man who wasn’t straightforward and assertive.

5. It opens up a whole new world of sexuality. Older men are more experienced so they know how to make you feel comfortable. They are also much more appreciative of a young body. I think they even appreciate the ‘flaws’ more. Because the ‘flaws’ of women their own age make a woman’s ‘flaws’ at 21 seem endearing. At least to the shallow douche-bags who sleep with younger women.

6. They are just so, so, damn appreciative. I cannot get over this. The best sex I’ve ever had was with a forty-two year old man. He was always so generous in bed. Like a sexual Jesus. We had hours of amazing sex any time we were together and it always absolutely blew my mind. He spent 40% of the time just admiring and exploring my body. That in and of itself was a major turn on. Older men get a look of awe and excitement in their eyes like they’re opening the best present in the world.

7. There’s something hot about the increased… physical substantiality. They are just a little bit thicker than they were when they were younger. It’s sexy because it gives them a bigger personal presence. I like the feeling of being with something strong and real.

8. There is an endless sense of mystery. These guys could be totally lame, if I were to look at it from a different perspective (like their ex-wives for example). In fact, twenty years from now I’ll probably think they are the creeps. But for now, these men are abstract and smoky images of man-gods who bless me with their presence a few times a week if I’m lucky.

9. It’s actually a pretty sweet set up. I don’t ever have to see their bad side. I don’t ever have to hear them go to the bathroom or clean up their mess. I don’t have to worry about whether or not we cuddle or sleep apart in bed that night. I get to love them from afar. I can love them for all that I imagine they could be, for the rest of my life. Hypothetically, staying in this state of limbo means you can indefinitely postpone the crushing realization of how disappointing the person you’ve given so much of your life to, actually is.

10. They have a lot more power than me. Their own lives are so full that I am only a passing thought on a free night. They’ve had their heart broken a million times already. They’ve already slept with a girl who was infinitely hotter than me, and a girl that was infinitely less attractive than me. I’m the last go-round on the only ride still left during closing time at the carnival. I want to feel important. I want to feel like if I never responded to them again it would bother them. Or at least that they’d notice. I constantly feel like I’m at the mercy of their whim. I am so eager to continue the relationship that I’d drop anything, whenever they want me or have time for me. I put my life on hold for someone to whom I’m like a new car. Interesting and entertaining at first, but eventually fading into the margins of their life once the new wears off. TC Mark

Read This