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What It’s Like To Date A 50 Year Old Woman, When You’re A 25 Year Old Man

Does it make you emotionally mature, or a sugar baby? We find out.

Whether you’re worried about libido compatibility, stunting your financial development or “mum jokes” there is a lot to consider when dating an older woman.

However, armed with the tales of the following men, you can at least be a little more confident in your own endeavours (or live vicariously for a minute).

Sure: eHarmony says “age is just a number,” and while there’s some truth to that; lived experience shows it’s not that simple.

These are the advantages, disadvantages and insights you only get from going out with a cougar.

The “Mum” Jokes Will Get Old Real Quick

One young man on Reddit revealed that your mates’ (or even your date’s) repetitious sense of humour can really get under your skin: “Dated a lovely woman that was exactly twice my age. I was 25 and she was 50. She… had three grown children, two of which were older than me. Her ex and her kids treated her like shit, and unfortunately she let them. Together we made a life running a business together that was successful enough for us to afford two homes, three nice cars, and a boat. Eventually I realised that while I had a damn good life, I was not happy.

“Age is not just a number. It eventually gets to the point where you can see the huge difference.”

“I got tired of the mum jokes and I was totally out of my element when her kids visited. I hated how they treated her and it became a source of contention for us.”

It Doesn’t Always Have To Be Serious

Another Redditor on the same thread, however, said it didn’t always have to be this way: “I myself recently met someone twice my age and we hit it off really well. Immediately, I knew that there was no longevity to any of it; what could I possibly offer someone emotionally who’s raised a full grown kid and gotten divorced?”

“I made my intentions known and thankfully they agreed.”

“We’ve remained good friends, he continued, “And see each other every other week or so. We really have a lot in common and enjoy each other’s company. When people ask about us hanging around each other I laugh and tell them about the amusing conversation we had about how much we do not want to date. It’s a great great dynamic and I’m glad we have it.”

She’s A Level Ahead Of You In “Life”

A further source of contention is demonstrated by the following man’s story: “My SO is 9 years older than me… She has a career and makes 6 figures where as I make about 1/5 what she does and still am not successful in my career… She has 9 more years of life on me where she’s had to figure her life out but still expects me to be on her level. It can be frustrating.”

But Not Always…

“Wife is 10 years older than me. We’ve been married 14 years. Ironically, she’s the naive one and I have way more life experience so it kind of balances out.”

Just Because They (Might) Have A Lower Libido, That Doesn’t Mean You Can’t Have Good Sex…

Although the age-gap can lead to libido compatibility difficulties, the first thing that one young man noticed about being with an older woman was that, “They know what they want in bed so the sex is mind blowing.”

Dating An Older Woman Can Accelerate Your Maturity

Dating someone older often comes with a lot of baggage (and maybe even a couple of kids). And although there are obvious downsides to this, one positive is that it can teach you life skills you would not otherwise have learned so quickly.

“The emotional maturity is probably one of the most attractive things.”

As one guy points out: “She’s emotionally mature, so there’s never any drama. If there’s something we disagree on (which I can’t even think of an example for), there’s no contention.”

But: If She Treats You Like A ‘Sugar Baby’, You Might Never Learn To Look After Yourself

“I know someone who ended up marrying his (sugar mama),” says one man. “He was aimless, poor, and lacked any kind of ambition in his early 20s but he had the luck of being very good looking. Happened to catch the attention of someone a little older than him who came from a fairly well-to-do family and who was herself very driven and upwardly mobile. Since they’ve been married, he’s mostly worked part time jobs and had stretches of being unemployed.” (Via Reddit).

“He gets to live an easy life, but it comes at the cost of his dignity.”

“He doesn’t have a say in much,” the ‘friend’ continued, “He loses basically every argument by default, and any time I’m around the two of them for more than brief stretches I can tell that he feels emasculated and absolutely hates it.”

Other users echoed this sentiment, saying that often when you date someone older the power dynamic can get blurred, which (many users reckoned), “Damages relationship dynamics for when you inevitably break up and actually have to start initiating with other people.”

RELATED: What It’s Like To Date An Instagram Model – According To Their Boyfriends 

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