Dating a Younger Man: Senior Dating Dream or Disaster?

Dating can be difficult at any age, so should you consider it a challenge in your 60s? Join us in conversation with dating coach Lisa Copeland who has some inspiring advice to share. Enjoy the show!

Margaret Manning:

My guest today is Lisa Copeland. Lisa is a dating coach who works with women over 50, helping them to find a quality man. Welcome to the show, Lisa.

Lisa Copeland:

Hi, Margaret! It’s nice to be here.

Margaret:

Thank you. So, you’re here to help us find the right man, right?

Lisa:

I sure am. It’s possible.

Margaret:

When you ask people in our Sixty and Me community about their view of dating, they’d respond with either hopeful, wonderful or disaster. Many have had experiences on both ends of the line.

Of course, it doesn’t have to be a love relationship you’re after. You could have a spectrum of friendships with guys. My question for you is, what do you think about women in their 60s dating younger men?

Lisa:

I think it’s great. I don’t think you should limit yourself to a specific kind of guy that you think you want – or you feel is appropriate – to date. If men are attracted to you, try it out. Why not? You have nothing to lose, and it could just be a lot of fun.

You don’t have to go looking for a marriage partner. You could have a lover. You can have a guy that just comes over once a week. You can have a communal relationship. You can live together, or not live together. Why not try it out and see what it feels like?

Margaret:

That’s a great answer. I think, though, that many women in their 50s and 60s still think that a relationship can mean just one thing. What you just said is to expand our definition. A relationship doesn’t have to be that serious.

I actually have a personal question for you. I enjoy a monthly travel trip with a wonderful group of people over 50, men and women. We share similar interests, and it’s lots of fun to travel together.

We had a trip last week, and I had the feeling some of the guys were being flirty – asking nice questions and probing for information. I could really tell they were interested in me. So, we got to talking, and while discussing all the places I’ve lived and events that happened in my life, I started thinking, “Oh, my God, the years are adding up.”

These guys are in their 50s, so when they asked questions like, “How old is your son?” after I’ve talked about my son and his child, and I replied, “34,” I just saw them doing the math. They were probably thinking, “34 plus 30, plus… Oh, my gosh, this woman must be like 80 something.”

What do you do when you’re in that situation with a younger guy, and they ask you questions that point to your age? What would you say?

Lisa:

You’re an honest person, Margaret, but you have to take control of such situations. So, when a guy asks about your son’s age, you could say something like, “Well, my son is 34, but I’ve got to tell you something. I am (fill in the blank) age.” When you throw it out there, you’ve got control, and you’re not worried what he might think.

I was on an airplane once, and a young man sitting next to me showed me these diamond rings he was selling for an event. I said, “I have kids your age,” followed by, “I’m going to be 60.” He looked at me and said, “Really? I thought you were younger than that.”

So, when you throw it out first, then it’s not a big deal. You’re not hiding it – you’re proud of it.

Margaret:

I think a lot of women do worry about the age difference and how they would appear to younger guys. Perhaps it has to do with a feeling of guilt. But if the guy is interested and you feel young, dynamic and sexy, why not? What’s your advice to your clients?

Lisa:

I tell my clients to always be honest about their age. If you feel good about your age, and share it with confidence, the results are much different than when you blurt it out as if your age is a menace to beware. You have to really come into your age and appreciate where you are because it is empowering.

I think one of the things that blows our confidence to pieces as we go to online dating sites is seeing that men in their 60s look for women in their 40s. That really scares us.

A friend of mine used to run a speed dating service. When the guys would come in, they always tended to want to meet with younger women. My friend would tell them, “No. I want you to get to know some of these women first. Then we’ll talk. If you still want to go to the younger ones, I’ll let you go.”

When the guys came back to her, they’d say, “I didn’t realize women my age were so amazing.” But we share a history and that’s hugely important. We all know the historical events have happened in our lifetime. Whereas, when you’re going with someone from a different generation, your history is very different.

Margaret:

Yeah. There’s no common ground to fall back to.

Lisa:

That’s why it’s scary to us to go out with younger guys. Our minds tend to focus on our age-related fears, “Oh, my God, if I tell him I’m 65, what’s he going to do?”

Margaret:

When you stop to think about it, though, what does it matter? If your age is a problem for them, then it wasn’t going to work out anyway.

Lisa:

I have a cousin who’s dated a guy 15 years younger than her for the past 15 years. She’s in her 70s now and he’s in his later 50s, and it’s been a great relationship.

So it starts within you and how you perceive your age. If you’re embarrassed or afraid of your age, that gets projected out there. If you feel good about your age, then you share it with confidence and people think, “Wow! I don’t think that person look that age.”

Margaret:

Here’s an important point then: if you go on dating sites, or just look around for possible dating matches, you will find that most older guys who have means, power or position, are always looking for younger women.

I think a lot of marriages have been broken because the man found success in his life and decided to look for a younger woman. That’s one reason why women don’t feel confident about their age. Have you seen that happen?

Lisa:

I have, but I’ve also seen situations where men have left their wives for women of the same age.

Margaret:

That’s true.

Lisa:

We tend to focus on the younger ones because that’s our fear, and that’s where our minds are focused. But men, and women, leave relationships for all kinds of reasons.

Margaret:

I have a lot of younger guy friends because I really do like millennial people. I believe the 30-40-year-olds are so innovative, and I make it a point to go places where there are young people.

Here we have a place called The Hub where entrepreneurs can go and just hang out and meet new people. I always love conversations with young people, but I think it’s relationships in the sexual or emotional realm that make us feel insecure. But maybe there’s no reason to feel that way.

Lisa:

So, let me give you a tip about men in general. Men either love you, or they don’t. If they want to pursue you, that means they love your energy and they love who you are. We are the ones with issues about taking our clothes off.

Men don’t pick out our parts and pieces. I know when men are younger and have those firm, tight bodies, it’s hard to believe they won’t look at our saggy whatever with distaste.

But if they are sexually attracted to you, they’re not going to care. You have to get into a mindset of thinking that if a guy wants to have sex with you, and you agree, he knows you’ve got saggy stuff under there. He knows that. It’s in our heads that we are afraid of it.

Margaret:

That is a good point.

Lisa:

Yeah. He likes you and he is sexually attracted to you. He would never pursue it if he wasn’t.

Margaret:

And it’s not just physical sex. Men are intrigued by our mind, by our interests, because we have great stories. We’ve had adventures. We actually have substance to us, so there’s a lot more than just the physical, for sure.

Lisa:

Yeah. Exactly.

Margaret:

On the other hand, there are a lot of older guys available. The thing is though, we may not consider them dating material because they may look too old. What’s your opinion about that?

Lisa:

We’re a generation that wants to stay young forever. Really, we’re the first generation to be consistently out there dating and looking for potential prospects online. I remember my shock when I first went to an online dating site. I’d look at men’s pictures and I’d go, “That looks like my dad or my grandfather.”

Looking at the pictures of my first high school reunion after 30 years of not seeing these people, I thought they all looked like their parents. I thought they looked old, unlike myself. That’s because in our heads, we think we look younger than we really are.

We go online with that kind of mindset and no wonder men think they see their aunts or grandmas, and we think we see our fathers or grandfathers. They look old, we look old.

First of all, we all age at different paces. Somebody’s face may look older, but the energy inside can still be that of a 30-year-old. It is worth giving them a chance.

My guy is four years older than me, and to me, he is the most adorable guy in the world. But he takes terrible pictures, and that’s another reason why we miss good guys – we judge very quickly based on a picture.

That’s a hormonal response within us that comes from the biological instinct of selecting a breeding partner. But we’re not living in that time anymore. We’re not looking for a guy to have babies with, we want support, love and companionship.

Margaret:

I’ve thought about that a lot actually. Social media is full of pictures of people that instantly look like a great match because they look so beautiful together. Then there are those people who don’t have that traditional kind of beauty, but you notice something else about them that’s captivating.

For instance, I’m fascinated with Julia Roberts and her husband. The woman voted as most beautiful in the world has not found someone like George Clooney to nest with. She’s found a guy who looks ordinary but has captivated her. I think it’s brave and freeing not to take people based on their appearance.

Lisa:

Yes. The biggest problem with online dating is that it’s one-dimensional. You’re looking at a picture and you’re reading what someone wrote about themselves. Based on that, you create your own story about who you think they are, but it’s not the real story.

That’s why when we meet people we always think they have lied to us. Sure, some people do lie about their age, and their weight, but mostly they just don’t match the story we created in our heads.

So we go online, we see an older guy, and we think, “He’s too old for me. He’s going to be a couch potato. He’s not going to do anything.” You don’t know if that’s true. He could be out there running. He could be doing lots of things, and he could be a great companion for you.

It’s worth giving older, younger and same-age men a chance. You’ve got all these potential possibilities if you love you and where you are in life. The secret is being comfortable with your age. Don’t lie about your age as you don’t like being lied to either. Also, it sets men up to think, “Ok, if she lied about her age, what else is she going to lie about?”

Margaret:

That’s great advice. Thank you, Lisa. Online dating has replaced the traditional kind as it’s much more convenient to look at your options online. It’s easier to get to know a person online and then take it from there. You just need to trust yourself and be proud of your age.

Lisa:

Yeah, be proud of it. Our generation does look younger, compared to our grandparents who did look their age.

Margaret:

I love having you here, Lisa. Thank you again for your wonderful advice about dating younger and older men. See you again.

Lisa:

Thanks, Margaret.

Margaret:

Bye for now.

Are you conscious of your age when guys approach you? Do you hide your age or do you share it proudly? Please join the conversation below and share your dating stories with younger or older men.