Tips for Dating Older Women with Money

Costing-Out a Cougar

Young guy, older woman—there’s often a greater discrepancy than age: income. In the older man-younger woman scenario this issue is, well, rarely an issue at all, really. We talk of Sugar Daddies and have a socially acceptable chuckle over it. So why are Sugar Mamas not looked upon as favorably?

If you ask me, the simple answer is sexism. In fact, I struggle to find another. It’s all just part of the long line-up of things that men can do without question, but women can’t—certainly not without raising eyebrows.

The great thing about women who date younger guys is that they (the older women) are usually far too confident to give a shit about such discriminations, so, no worries there. The problem usually lies with the young guys, who can feel emasculated by the thought of having a woman covering their costs.

Within my circle of friends, when it comes to paying, I prefer a method that has nothing to do with gender: everyone takes a turn, and in the end it all evens out. (Sitting at a restaurant table doing math in order to ensure an even split is something I find annoying and cheap. I tend not to go to restaurants with penny-pinchers.)

It’s not uncommon to be showered with generosity when dating older women. Such an age difference usually means the older person (in this case the woman) is more established in their career and is the one with more money to spare. And I’m not just talking restaurants. In a most generous of scenarios, she might offer vacations, clothes, a high-rollin’ lifestyle, whatever. Here’s what I say:

If you can afford to pitch in, then take your turn the way you would with any friend. Sometimes you can insist on treating for any of the items mentioned above. Sometimes she can insist—in which case you should (like they do in Europe), accept graciously. If, by some stroke of bad fortune you don’t have a pot to piss in, but the older woman you’re dating insists on pampering you, then, once again, accept graciously.

There’s nothing wrong with it at all, on the following conditions:

1. You’re not taking advantage of her (which, if so, is because it’s in your nature, and hopefully she’d suss that out soon enough and drop you like the scoundrel that you are).

2. She’s not trying to “buy” you, or “own” you, cuz that’s just icky on her part, and shame on you for playing along.

For obvious reasons, I’m hardly about to name drop on a dating site, but I can tell you that I’m personally connected to a certain high-ranking government official in the federal finance department who once told me while we sat in a fishing boat, “Y’know, it’s only money.”

Don’t let it get in the way. And don’t fight over it.

And no matter how rich you think your woman might be, don’t expect it.


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