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dating an older man advice

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Dating someone five to 10 years older is not a huge deal, after a certain point in life. Obviously, when you’re 16 and want to date a 19-year-old, your parents aren’t having it. And when you’re 20 and meet a 30-year-old, there may be too many differences there to make it work—your parents still pay your bills and your boyfriend is well into his career. But later in life, a five-, 10-, and sometimes even a 15-year age difference doesn’t really matter. A 45-year-old can easily connect to a 57-year-old. They may both have kids, careers, divorces, property—the whole thing.


But what about those couples with a massive age difference? Think twenty years or more. We’ve already explored how women feel about dating men much younger than themselves here, but what about 30-year-old women with 55-year-old boyfriends? What about these 28-year-old women (girls?) getting involved with men in their late forties? You see it happening! Living in a big city, I see it all of the time. Big cities really embody the saying, “60 is the new 40” and “40 is the new 30.” You wouldn’t believe how often men in their fifties and sixties hit on me, a woman in her early thirties, like it’s nothing. It’s clear that society has told them there’s nothing weird about that!



The thing is that…60 isn’t the new 40. Sixty is 60, and all that comes with that. And 40 isn’t the new 30. Forty is 40 and 40-year-olds should, I hope, feel that they are different (read: far more mature) than someone who just left her twenties. As much as we can pretend that age is just a number and it’s that human connection that counts, age will catch up to you. Biology doesn’t care what you feel about age. On that note, here’s what the future holds if you date someone much older than yourself.



Health advisories apply to him

Many young people right now have the luxury of looking around at the current coronavirus pandemic and saying, “My friends and I will be fine. We’re young.” But if you date someone much older, you may find that when certain illnesses go around, your partner is in the most vulnerable group. He isn’t young. And if he becomes ill, he may not be fine.


Prepping him for a colonoscopy

Most people under the age of 50 don’t need to think about a colonoscopy let alone interact with one in any way. But if you have a partner who is much older, he could be facing regular colonoscopies, meaning you’ll be there for the not-so-pretty preparation and recovery.


Relying on sexual, eh-em, enhancements

Let’s face it: young men can get erections even when they don’t want them. They can keep them for a while. Older men, however, often cannot get an erection, even when they are aroused. If you date a much older man, you may find that you took natural erections for granted all these years.



He’s not a hypochondriac; he’s right

If you have a young partner, and he has any sort of symptom, you might say, “It’s probably nothing. You’re fine. You’re being a hypochondriac.” But if you have a much older boyfriend, you don’t get to say that. It’s even irresponsible to say that. If your 60-year-old boyfriend has a brief chest pain, you send him to the doctor.



Getting the senior discount too early

You may find, when shopping at a certain store, getting movie tickets, buying theater tickets, going on a tour, or all sorts of things, that the cashier says to your partner, “And you get the senior discount.” Woah. You weren’t ready for that. You always imagined that that was just for people with walkers and hearing aids. Not your boyfriend.


Some awkward financial talks

Financial talks get real—really real. When your partner edits his will to include you, first off, you realize this scary thing: he’s had a will for decades now. Then you realize that, any changes he makes to his will, at this age, may be the final changes. The will is no longer just some thing he made to be responsible “Just in case.” That “Case” may be coming soon.


Attending funerals early

If your partner has friends older than himself, then his friends may be passing away. You may be surprised to find that you’re spending some of your Saturdays at funerals and memorials for your partner’s friends. There is almost no way to describe the shock, sobriety, and depression that can come with that.


Being a caretaker

Slowly but surely, you can find yourself being a caretaker. You have to remind your partner to pack his medications when you travel. You have to tell him that it’s not safe for him to do this or that, due to his condition. If there is any physical task to be done—take the dog for a jog or climb into the attic to get something—that may fall on you, because you’re the young one.


Caretaker disputes with his kids

When your partner becomes quite old and his care needs to go in the hands of professionals, you’ll be making those decisions with his children. You’ll have arguments about it. And you’ll realize you both know just as much—or as little—about this because you’re around the same age.


He retires far before you

He may retire a good 20 years before you. That leaves him with plenty of free time to travel, go to day spas, golf on a Tuesday, and generally relax and have fun. But you’re still in the throws of your career, so you can’t join him. And you may start to worry that he’d prefer a partner who was also retired and could join him.


Simply watching him age

If you’re around the same age as your partner, you may not see those signs of aging creeping in. They’re happening to you, too, so you’re blind to them. But when your much older partner’s hair turns grey, and when your much older partner struggles to get up from a low chair, you notice. And it’s jarring.


And battle aging

You’ll also watch your partner battle aging. He may start to dye his hair. He may begin to lie about his condition, telling you he feels fine when he clearly doesn’t. He may try to dress younger. When he battles his aging, it only makes his age stand out even more.


Getting a puppy can be weird

This may not apply to you, but if you two want to get a puppy together (this happened to my friend who is 40 with a 65-year-old boyfriend) it can get weird. You can have a moment when you realize the dog may outlive the man. Or, at least the younger person will be entirely responsible for physical activities with the dog.


Making any long-term, joint investment

Really making any sort of long-term investment together can get weird. If you want to buy a home together and take on a 30-year mortgage, you realize that the mortgage will outlive your partner. One day you’ll be making those payments alone. If you simply want to buy a timeshare that will expire in 10 years, you think of how very old your partner will be when it expires.


Your politics can diverge greatly

The politics of the young and the old are often different. Your partner grew up in a different time from you, and sees things another way. The older he gets, the farther apart your politics, and your general views on the world, may become. You can find yourselves getting into more arguments.

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