The joy of boy toys

Younger men. Sometimes decades younger. Perhaps young enough to be your son.

I’m not usually drawn to them because they are typically even more immature than the fifty-somethings I tend to date. And I abhor the concept of and term “cougar” so would never want to be accused of one.

But every once in a while a younger man comes along who is worth considering. And if there’s mutual attraction, it can be great for your ego — as well as fun!

A few months ago I had a few dates and continue to be contact with one such man. He is more emotionally mature than many of the chronologically mature men with whom I’ve gone out, despite his being 20 years my junior. He’s handsome, interesting, thoughtful, intelligent — and he thinks I’m sexy and, in his words, “gorgeous.” I usually only get that from the near-sighted men closer to my own age.

Yesterday a 40-year-old colleague called and the topic turned to his 63-year-old widowed mother who’d begun dating. He’s been helping her write her online profile and vetting prospective suitors. It got him thinking about if he weren’t happily married. He blurted out, “If I weren’t married, I’d definitely want to date you.” Sweet man. Of course, when one is married, it is very safe to spew such sentiments. Toward the end of the conversation, he said he thought I was “smokin’ hot,” which made this overweight, crow’s feet-festoon 55-year-old feel very nice indeed.

Several friends have long-term marriages with younger men. I could see how it could work if the couples were compatible. After all, in the grand scheme, does age really matter? He could have health challenges before she does. And since women’s life span is longer, she’d be able to have a sweetheart into her elder years.

Most of us don’t like to think long term. We want to enjoy the magic of now and believe we’ll figure out what we need when the time comes. So why not embrace the situation if a there’s a mutual attraction with a younger man and see where it goes?

As long as you both are clear that you want similar things out of life, then an age difference doesn’t really matter. However, my experience is that a man a decade or so younger typically has children at home, or is consumed by his career, or doesn’t really have time or the means to travel or accompany me in the life I’ve created. If so, great. But I’ve found it’s rare.

So should you throw caution to the wind and play with your boy toy? Or is that disrespectful to him, implying that you will discard him when he’s no longer fun to play with? But isn’t that a possibility no matter what his age? And, of course he could jettison you just as easily.

What’s your philosophy about midlife women dating a man over a decade younger? Have you done it? What did you learn?


Want to explore more about who you want as your next sweetie? Get your copy of  In Search of King Charming: Who Do I Want to Share My Throne?


10 responses to “The joy of boy toys”

  1. Lila Avatar

    How much younger is it to be appreciably “younger”? I think a couple of years doesn’t even count.

    But, I just turned 49, am interested in a single (& no kids!) friend who is 42. We share a group of friends & activities. I hesitate to express interest, because I don’t know if he would consider that a significant age difference.

  2. Karen Avatar

    Years ago before I was married (I later got divorced) I dated a “younger man” for about a year–I was 35 and he was 28. It was fun, but there was definitely a culture gap–we knew and listered to different eras of movies and music. Ultimately, he decided the age gap was freaking him out too much, even though (snicker) everyone usually thought I was younger than he was (he lost his hair at a young age).

    These days (I’m 50) I’d love to date a younger man–especially since I’ve recently dated mostly men older than me (they’re more mature and available). But I’ve realized that for me, now, dating a man 10-15 years older, or even a few years older, brings up a lot of worries about what might happen if the relationship turns long term.

    Men just don’t live as long as women, and this gets to be a problem if you’re already middle aged when you start dating a man. Re one guy I dated who was 13 yrs older than me–his age did make me wonder. He was physically active, but he was already “slowing down” in terms of being careful not to overdo it etc. Would he still be “around” when I retired myself? A woman of 65 can expect to be very active and (knock on wood) healthy with at least 20 years ahead of her. But I a man of 78 (which is how old hell be when I’m 65) is…well…pretty old at that point. I’d like to find someone I can enjoy retirement with.

    I think that maturity doesn’t necessarily correlate with age, so why not date a younger man at this point? I’d be open to it, but I haven’t dated anyone younger than me in the 6 years since I got divorced (except first date meetups that didn’t go beyond that). I personally feel that most divorced men are really looking for a woman younger than themselves, and if they’re not total jerks they won’t have a big problem finding a woman in her 30’s who is very happy to be with them.

  3. Lisa Avatar

    For the past six months, I’ve been dating a man who is 19 years younger than me: I’m 44 and he’s 25! He approached me online with actual conversation starters (unlike other youngsters who approach with sexual advances only), and we quickly found several common interests. We met after work one day near an outdoor farmer’s market, had a second date a few days later and went on from there.

    What struck me most about the courtship was that he was so free from the emotional baggage that anchors so many middle aged men. I found it refreshing to actually have meaningful conversations about something other than tales of wives and lives lost.

    I was embarrassed, however, to tell my friends about the great guy I had met because of our age difference. When I introduced him to a few friends at dinner, they immediately assumed the relationship could be purely short term and physical. I think our culture simple cannot accept the potential for sustainability when the age difference is so great, especially if the woman is older.

    I don’t know what I’ve learned so far — maybe just that sometimes you need to follow your instincts even if others around you stand in judgment? or maybe that it’s simply foolish to cut off a budding relationship because you are afraid of possible future scenarios? I think people need to find their own ways…what works for some won’t for others, and we should all learn to be more tolerant of deviations from the norm.

  4. maria rose Avatar
    maria rose

    there is nothing wrong with the idea of a younger man with an older woman (take Cher or Demi Moore) if they both have similar interests. like the comment before me stated a woman has a longer life span than a man so as we age (gracefully) the need for companionship into our latter years grows more. i don’t intend to live apart by myself if i can help it but i would rather live with company to share my time with (after all i won’t have to work) if given the choice between living with one of your children or a companion what would you chose

  5. Elena Avatar

    That has been happening to me quite alot lately! I just turned daughter is 22.. well, her friends I have met lately, I was excited and actually wanted to date a few of them! I am always attracting younger men.. I am mature, but still have a “teenage dream” (like the song says it all: Katy Perry)… I love to have the younger guys.. they are more my “speed” if you understand what I mean!
    I got married to someone 14 years my senior.. even though he did not “LOOK” like he was older.. but I thought I could “settle down” at that point.. sooo funny.. why would I want to do that?? lol…. anyway.. it was HORRIBLE..I was ready to go dancing.. and he would sit there with his newspaper not even looking up to see what nice outfit I had on.. and they were “short” skirts! lol.. He ALWAYS stayed home.. no matter what… He was soooo set in his ways.. it made me BORED!! I mean.. why would I want to sit around the house all the time??!! I should of listened to that small voice inside me when I was ready to meet him to get married.. I was sooo sick and threw up in those “ashtrays” that “stand” by the elevators… AND.. he wore the WRONG clothes.. …our “best man”.. dressed sooo nice that night.. in a suit and everything.. and I spent that night with him.. gambling etc.. (unfortunately his is no longer with us (R.I. P. bobby)…
    well, I decided these last few years to date who I feel comfortable with.. I am dating someone now that is 34 and I’m 46… It’s good so far… lol.. I WANT to date even a younger dude.. he is 26.. but very put together and very very cute!.. I just know my daughter would NOT be happy!! I don’t think that is her business I’m serious.. I find myself this past year.. going out with a LOT of young men..and we have tons of things in common and have a ton of fun!! I like that!!
    It all started when I was 21.. I was seeing someone that was 48 or something..(he NEVER did tell me his age).. when the time finally came for us to be intimate, it was NOT what I expected at ALL.. and his body was sooo different.. saggy kinda..etc… I just was NOT impressed!.. later in the months ahead.. I started dating a man that was younger then me… When the time came for “us” to get intimate, it was SUCH A HUGE DIFFERENCE!! His body was tight and gorgeous.. and he kept up the speed and everything else! I was soooo impressed! Of course I kept the younger one.. and got rid of the Older man.. it did not matter that the young man did not have the “finances” together, or a house.. and a horrible car.. etc… but what did I really want?? I want to be happy!! All the time….Do you girls know what I am talking about?? lol.. I feel that I CAN date younger men all the time.. I have no problem.. if you feel good about yourself.. you can date anyone!! The ONLY thing that bothers that he will feel the same way I did with the “older” man.. like “MY” body is the one that is “sagging” and the young 20 plus girl’s bodies are tight and firm… it makes me sad! I feel that after a while.. they will eventually trade me or a NEWER YOUNGER woman.. to make themselves feel better.. people my age are going through their “midlife crisis”.. It’s funny also.. YOUNGER men.. DO FIND OLDER woman sexy.. and they get turned on..thinking we know waaaayyyy more than the young ones.. plus.. the “conversatiions” we have .. they don’t like the younger girls.. how they attach themselves and their is NO conversation… ! It’s a double edge sword”
    All I know is.. I’m going to continue to date “younger” men.. I don’t care.. I feel comfortable.. except for the KIDS in the house.. and the “baby mama drama”.. that is NOT cool.. but I guess you can’t have it both way.. so you need to make up your mind right??
    I hope everyone gets to experience the “younger” man… I know I do.. and I always will..I just don’t want to look “too” old next to him.. right now.. it’s all good.. so I am going for it!! Wish me luck.. and right back at all of you!!!

  6. Richard Avatar

    From a longevity perspective, it is better for a lady to be with a younger guy. However, the reverse is more typical. By the time you are 40+, the persons are adults and can make the decision for themselves. If you are the older person, it is the responsible thing to make sure you have a discussion about age the difference, and if the person still wants to stay in the relationship, then why not? By addressing it, you show the other person respect. I dated a lady who was 12 years younger. She preferred older men, and did not want to have kids.

    If your intention for the short-term (“discard him when he’s no longer fun to play with”), then that is a different discussion. If you both want a short-term relationship, then isn’t it ok if you both knowingly “use” each other? Are not adults allowed to do things with mutual consent?

    In your 20’s, 10 years makes a big difference in maturity level and stage of life. At 40+, the differences are much smaller (or very individual – their children can be old/young or both). A 40+ person can easily be physically 10 years younger or older than their chronological age. If everything else lines up (see yourself spending the rest of your life with the other person), why should chronological age be an issue?

    When there is more than 10 years difference, I think what is unspoken is whether there are psychological issues involved. If the other person is attracted to what you represent, rather than who you are, I think you owe it to the other person to help them work through the issues before committing to a long-term relationship.

  7. Yvette Francino Avatar

    I’ve tried a couple of times. The first time was a disaster. I was flattered that he was interested, but it was clear we were in completely different stages of life.

    The second time I tried it, it lasted for about a month, and I was the one who called it off. It just was hard for me to take the relationship seriously when there was such an age difference. And, once again, we were in different stages of life.

    It may not always be the case, but I think many times the “boy toys” are looking for a relationship that will not lead to marriage– maybe commitmentphobes. They often are looking for a no-strings-attached sexual relationship and they figure an older woman is “safe” for that because a long-term commitment is usually not expected.

    On the other hand, age is just a number, and if both people are in the same place (maybe neither wants commitment… or maybe they both do and are OK with the age difference) than more power to ya! Who cares what others think? Do what’s right for you.

  8. Mike Lowrey Avatar

    I think Anna Nicole Smith & her tycoon hubby was a problem.
    Anything else short of 25+ years seems fine to me.

    To anyone contemplating it…I say go for it and see where it takes you. You never know. It takes a dollar and a dream to hit lotto. The odds of someone hitting lotto is slim to nil but people still have that hope. Folks hated on Demi but her relationship has lasted longer then most.

    Age is just yet another way of dwindling a person’s possibilities for a mate.
    I could say I dated a skinny girl and it didn’t work out, so I don’t want to date another skinny girl. But what sense would that make. I’d rather take each person for face value and see how things work.

    Love doesn’t have boundaries, that’s why it’s called love.
    The flip-side of that is to only date folks your own age…Is that working out for everyone?

  9. Mitsy Avatar

    I’ve written about this before, but I’ve ALWAYS been attracted to younger guys. Maybe it’s partly because some men my own age (50) look so much older than they are. Forget someone who is 60. It would never work for me and someone that much older. But, I do have my limits on how young as well. I’d say 10 years is about my limit. However, I had a weird experience with a car salesmen who was almost 15 yrs. my junior who flirted and hit on me. Turns out he had a “former” girlfriend living w/him. Yeah, I’d say he had some issues along with the age (immaturity) thing going on. I deleted him from my Facebook account and needless to say, I won’t be buying a car from him.

  10. Richard Avatar

    I have dated a few ladies whose mother’s are also single. When she is 10+ years younger than you are, her mother might be closer in age. If things don’t work out with the daughter, it would be odd to strike up a relationship with the mother.