Slim pickings. Is that how you feel when you think about dating?

I’ve said it forever. When you’re in your 20s, there’s just this abundance of people to date. You can get on Tinder and swipe and meet some of these people. You can stumble into a bar and meet someone. Everybody’s open to a new adventure because they haven’t experienced so much in life yet. They’re so open to experiencing the newness of love and the newness of relationships.

Getting Older in the Dating World

I got an email the other day from a gentleman.

It’s an interesting email, and it’s something that we really need to talk about, something we really need to dive into.

To the women who are reading this: don’t get offended at all. I totally understand where he’s coming from, and it’s not meant to offend you. So please read it, and have compassion and understanding.


I’m 56-years-old. I’m in great physical condition.

I’ve had a wonderful life. I’ve got a beautiful daughter and a beautiful son.

I was married for five years, and I’ve been in and out of relationships my entire adult life.

But all of a sudden, I feel like the pool of women I’m attracted to is drying up.

I’m a huge football fan as you are. And I think that this will help you understand the predicament that I’m in.

You remember when Brett Favre was playing for the New York Jets and the Minnesota Vikings, he was a B-list, haggard man?

It felt like he was a ragdoll being picked up off the turf.

You know when Brett Favre was younger and you looked at him all fresh, in his prime, and you thought to yourself (if you were a Jets or Vikings fan), if only we drafted him back when he was young.

I feel like the women I’m dating are in the latter stages of Brett Favre’s career.

I know that’s superficial. But I don’t know what to do.

I’m a good looking guy, like yourself. I stay in great shape, and I’ve dated beautiful women my entire life.

But the last couple years have been really difficult. I feel like I’m suffering from a disease called old-man-itis.

The younger women I find really attractive are sometimes too young for me emotionally. The women in their late 30s and early 40s that I want to connect with sometimes think I’m too old, because they think that they should be somebody younger, because I look great. I don’t know what to do. Help.

Jim, New York, New York.

Jim, I get it. I get it, I understand. As a man, we are so much into looks. Now, don’t get me wrong, if you’re reading this and you’re a woman, looks do fade. But when you’re dating beautiful women your entire life, you’re looking for that beautiful woman on the inside and outside still.

And don’t get me wrong, we’re all going to get old, and our faces are going to drop and our necks are going to look like chicken gizzards. And our socks are going to be pulled up to our knees and all of a sudden we’ll be wearing big, white sneakers that look like they are five sizes too big on us. It’s inevitable. But part of aging is also realizing that you had a run. You had a run with young, beautiful women, and now may be the time to look at an older, beautiful woman and realize that that is the best woman you can be with.

Maybe she doesn’t look like she did in her prime, but that doesn’t mean that her body hasn’t aged well, her face doesn’t look great and her spirit and soul are better than ever.

They’re out there, you’ve just got to find them.

Dating the Aging Woman

aging and datingYou’ve got to realize that you’re at a stage in your life where either you’re going to just date the young women and be a little bit of a sugar daddy to them and an experience, and be okay with that experience, or you can date the older, beautiful woman who will give you the connection you’re looking for.

If you keep dating the younger women, you need to be okay with the fact that there’s no long range in it at all, that you might have to hit the reset button every couple of months or every few years when a young woman decides that she really wants to be with somebody who is closer to her age. If you’re okay with that, then that’s fine. It’s your life, no one can tell you what to do or how to live it.

Me, I would prefer to be with somebody who has aged beautifully, who is closer to my age because there’s so much more to share.

I love looking at the younger women, I think they’re fantastic, and I don’t mind going out with them and hanging with them and enjoying their energy and their youthful enthusiasm. But I know if I want long-term, it’s going to have to be with somebody who is more in my 10 year swing, 10 year radius. Because it’s just going to be far greater for long-term success.

Aging is never going to be easy, there’s always going to be something about aging that is going to make you feel uncomfortable, whether it’s the way your body changes, your face drops, your neck looks like a rooster, or you start wearing the big, white sneakers. Or you can’t date the women you used to date.

Just realize, that’s the evolution of life. Life is exactly what you want it to be and how you want it to be. I know many men your age who date younger women and enjoy it. They don’t expect any long-term anything. They’re just enjoying whatever they’re enjoying.

But for long-term success, you are most likely going to have to date somebody who is in the twilight career. And there’s nothing wrong with that. She’s still beautiful inside and out, just a different way to look at beauty. And you’ve got to come to terms with that.