When the Woman You’re Dating is More Successful

I’m happy to lay down my spear and be a gatherer.

If I had the means I’d spoil my cougar rotten (although I do so in other ways). She, however, is successful, solvent and generous. I’m regularly showered with dinners and outings and gifts. I expect none of these things, but there’s no doubt they make for exciting times. I graciously accept.

In order for this to make me somehow feel inadequate about myself as a man, or whatever, I’d have to be:

  • riddled with insecurity
  • feeling guilty about “using” her
  • completely out of touch with gender equality and respect

I clearly have no problem being with an older woman, nor am I concerned about satisfying her in that oh-so-manly way. I’m not guilty because I’m not “using” her: I want to be with her, and I’d be just as happy if she didn’t spend a dime on me. And I think her success should be given the respect it deserves.

And here’s what I wanna know:

  • What’s so wrong about being proud of the woman you’re with?
  • Why can’t I bask in the glory of a woman who’s successful? She wants me there, and it’s fun!
  • Would it not be overlooked if an older man—successful, solvent—were wining and dining a younger woman—too young to yet be successful or solvent? I think so.

This kind of sexism runs rampant, but it’s rarely confronted openly or with any sort of resolve. Drives me crazy. I think it’s sad how so many young guys keep their relationships with older women hush-hush in fear of being ridiculed by their friends. It’s sad and it’s unfair and it’s unacceptable.

So why not make it easy for yourself and follow my motto:

  • fuck what other people say
  • tell her how proud you are of her
  • celebrate in her successes
  • appreciate any generosity bestowed upon you
  • reciprocate when you can
  • never mooch, and
  • fuck her like she needs to be fucked

Any questions?


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