Why Dating Older Men Seems Boring & What You’re Missing If You Don’t

“Ann” is a 50-something single woman, using online dating. She’s looking for an energetic, passionate and interesting man. The majority of men who are contacting her are old dudes; like in their 60s. Dating older men seems so freaking boring to her.

In a Facebook post, Ann recently asked why older men seemed so boring and like they didn’t have a life. (Keep in mind that the women participating on my private Facebook page range in age from their late 30s to 70s.) I hear this often since I specialize in helping women over 40 find love. I’m so happy to answer this question.

The answer is really about doing what I often do: Helping you better understand GROWNUP men. I KNOW that when you better understand men’s life experience and point of view, you will be able to broaden your perspective and, therefore, open up more POSSIBILITIES for LOVE to come into your life. Not only will it improve your dating life, it will help you develop better relationships with high quality men who just need a little ‘push’ from you.

Below is the Facebook thread about why some older men seem so boring. I’ve included the comments from the other women because I’m pretty sure you’ll relate to them.

(I have replaced names with initials, of course, but highlighted my comments.)

Palmer_Bobbi_Crush_047aaNEW Hi ladies! There is a convo about how boring older men are and how they turn you off. This is a big topic but let me share something about this. (There’s a lot more I want you to know but too much to share here.)

Women and men are actually alike in a lot of ways. But when it comes to socializing, men are completely different.

Women go out to eat, shop, travel, go to plays, chat over a glass of wine, take classes and join book clubs…all with our girlfriends.

Men don’t do any of that. Their socializing exists around sports or some physical activity. So if a man plays golf or sails (like Larry) he may partake in some regular activity and socializing.

Otherwise, his life can be pretty quiet.

Yes, it’s true: men can be waiting for a woman to fill in their life. So what?

This doesn’t necessarily mean they are a doofus, friendless or dull. It means that they haven’t been able to just call up a dude friend and say ‘hey Bob, I’d really like to see Paris. Wanna plan a trip?” Or wanna see a play, or have dinner? It’s not what guys do.

That means that when a man doesn’t have a woman in his life, especially if he’s retired or semi, he may not be doing much of anything.

But that doesn’t mean he WON’T!

My 65-year-old client met a 71-year-old widower. Together they are traveling the world and running marathons. He wasn’t doing either when they met.

And it’s not like she had to ‘make him’ do it…he loved adding that to his life! And he turned her on to things he loved to do, but needed a partner to do it with.

So the KEY is…

when you meet a man (or look at an online dating profile), don’t nitpick what he’s doing and not doing as much as what he wants to do or is open to doing.

Does he seem open to learning?

Is he curious?

Does he seem interested and excited to share things that you like?

What’s on his bucket list?

You may not see all this on the surface. If you like other things about him and he shows potential to have your must-haves, be willing to dig a little, sister. (If you want to learn how to dig by sharing with him to help you get to know him, read this article here.) 

Learn about him by sharing what you’re passionate about or what you want to do next…then pay close attention to his response. You’ll learn what he’s interested in, even if he hasn’t done it yet. 

I see this all the time: men, especially older ones, are thrilled to let us open up their world! And to be able to share his with you.  

Men and women have a lot in common. We also have a lot of big differences. The better we understand these differences, the more realistic our expectations, the more enjoyable dating becomes and the deeper our connections. THAT’S what leads you to grownup love!

We can’t expect men to be like us.

When you can open your mind to better understand how they think, live and love…you will start seeing the good men all around you. (You know…the men I keep telling you about and that my clients and other students keep meeting?) Good men are out there waiting for you. 


JH Great advice Bobbi Blum Palmer as always. Thanks for the reminder. This was one of the eye openers I had in your last workshop… never occurred to me where men are concerned….hope to dive deeper…can’t wait for your upcoming Online Dating course!

MS I briefly dated a 63 year old man (a few years over my ideal age range) who was still practicing law but was into yoga, concerts, dining out, etc. I also met a 68 year old who was very active with a civic group and participated in a lot of activities. Not the right fit for me fo other reasons but I have met older men who are still very active.

MB Bobbi, thank you for this post. I think there is a lot of wisdom in it. I have a question for you. I do think it is important that a man has friends, (and that I have friends also) so that we are not expecting our relationship to meet all our emotional and social needs. I think this ws a problem w/ my last husband. But I am not sure how that looks with men. One man I have been dating has a friend he hunts with a couple times a year, a couple of fishing buddies, and his kids to do things with, is that a normal healthy socialized male? It seems like he sees friends about once a month, besides seeing people at church. The other man I am dating is much more social, seeing friends and family several times a week.

LB  I loved these insights. Thank you!

RT   Thank you for this reminder, Bobbi. This is a good thing for all of us to think about.

AR  I guess I have still been looking for a ready-made kinda guy. I have already been through some relationships where I ended up making all the suggestions and taking the lead on shared activities. It’s true that in most situations, the woman is the social conveyor but it would be nice to have someone introduce me to his world and interests.

MS  I agree that we often consider someone too old without even getting to know them. I have known men in their 30’s and 40’s who are totally set in their ways and home bodies and I’ve met extremely active and engaging men who are in their 60’s and beyond.

Yah, I agree. There are so many men who are clearly very active. DD posted about this too – she’s meeting many. Just don’t jump to conclusions if they appear not to be at first. Like Norman (I mentioned above) he may be raring to go when he meets the right woman. (By the way we are having dinner with them tonight! They’ve been together 4 years and are SO happy!)

SE  There is a man who is 67 who is very interested in me. he is an artist travels does maintenance work.with his son and looks 10years younger!

LN   What an awesome perspective I had never considered before. I didn’t realize that guys aren’t socially active in the same way women are. I’ve been guilty of discounting some guys’ profiles because they weren’t active enough! Live and learn! 🙂

SS  MB, I think that is normal for a guy. Just like Bobbi mentioned, men don’t necessarily have the same friendships we do. Funny, my ex husband had (& still have more friends) than I do, however I do many more activities – I tend to do these activities on my own or with a couple female friends. I used to do stuff with male friends but realised I was being ‘used’! No more!

Palmer_Bobbi_Crush_047aaNEWYah MB, that sounds ‘normal’ to me. Very. Now that you understand what I wrote here, kinda makes sense, right? Larry had just moved here when we met and didn’t have any friends. And he didn’t really keep in touch with the guys back home because they couldn’t DO stuff together anymore. But he is very social, has made new friends and loves my friends.

LH   I completely agree Bobbi, I’ve tried to do just that. I will say, I’ve actually been a bit disappointed at times when I’ve been open with older men only to feel judged or criticized by the fact that I may not be a size 4 or 6. They’re so busy being proud of themselves for remaining in “shape” that sometimes they judge your size before they give you a chance. Not always of course, but… enough that it’s discouraged me

SF   I had been feeling that so many older men were dull too. They always mention loving to stay in and watch TV or movies. I assumed it was because that is what they did with their ex-wives and they forgot about what dating involves. But I recognize that younger men were pretty boring too before they dated me. LOL

EM  Bobbi I had forgotten I actually discuss this in my intro to communication class. Men engage in what I like to call “parallel play.” That’s the way they’ve been socialized. Little girls play house and play barbies (generally) that develops relational skills, while little boys play competitive things like sports or cops and robbers. Then when men grow up their friendships revolve around activities rather than relational communication and connection. Being with a woman gives them a gateway to becoming relational. (Sorry I’m nerding out, so interesting!)

Palmer_Bobbi_Crush_047aaNEWHey LH! Yah, there definitely are some guys that are in shape and only want the same with women. Though I know I used to just assume that they didn’t want my chunky thighs…now I know it was other things I did that turned them off. So sometimes our insecurity makes us assume quite incorrectly.
You got the words right: You LET it discourage you. It’s your choice to take it personally OR to think ‘screw you buddy’ and move on. Also, to all of you, if you’re just going for the 50/60-something guys who are handsome, make money and are in great shape…you’ve got a lot of competition. Try looking at the ‘normal’ guys, ok? (I’ll talk about this way more in my upcoming Online Dating course.) Glad you’re here!



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