Shoul you date a man who’s MUCH older?

by singlemomseeking on January 18, 2008

older-man.jpgA single mom friend wrote to me yesterday to update me about her dating life. I could send her back a long diatribe on what I think about her possible romance with The Older Man, but I’d love to hear what you have to say:

You see, my very smart, gorgeous, successful single mom friend — who’s turning 34 next week and has a beautiful daughter — recently met a 54-year-old man through work. He’s divorced and has three grown children. He has asked her out a couple of times and told her that he’s very attracted to her.

He has let her know how much he admires her for raising her daughter alone, and he even paid for sitters when they went out. So far, he has worked around her schedule (i.e., no pouting because she can’t see him every weekend). My friend says, “He seems very comfortable in his shoes. He calls consistently, and there are no games.”

She enjoys his company and feels attracted him. She’d like to let this get more serious… but, he’s 20 years older than her!

Single parents: help her out here. What do you say?

Have you ever dated an older man?

Should she go for it? Or, find a man closer to her age?

P.S. I’m going to encourage my friend to enjoy him in every way for now… He sounds like a decent man. But I also want her to be prepared for the fact that when she’s a hot 34-year-old with a teenage daughter, her potential partner will be asking for senior discounts.

Photo courtesy of Albatross

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{ 23 comments… read them below or add one }

Dave May 1, 2017 at 3:49 pm

Do people think they will live forever and an older mate will die ? Pass on loving someone for whatever reason, and you pass on love !


lisa February 22, 2013 at 5:22 pm

I’m 41, single mom, and I’ve been dating someone who is 25 years my senior for 3.5 years. He loves my kids but doesn’t want to move in with me. He had a bad marriage and was busy litigating for most of his life as a lawyer so never connected to his kids the way he wanted to. His grandson and my kids love each other. His kids adore me. But I’m lonly and want a life partner. I don’t know what to do. We love each other so much, it hurts to think of us apart.


john english "The Voice" April 6, 2017 at 8:03 pm

II am a 62 year old entertainer /singer performing a tribute to Frank Sinatra.Most importantly i am a proud father raising my son who has Down Syndrome.Raising my son on my own has its challenges but with so many rewards.I would love to meet someone my age but they dont want to be tied down with a child in the home.So I”m looking for a single mom who will love and accept my son as i would love her and her children.Age doesnt matter…..
Love does.


Maxine September 8, 2008 at 3:18 pm

I have read with great interest all the comments regarding age. I was married to a great guy who was 20 years older than I. We never experienced any lack of support from family and friends. We had a super marriage, which sadly ended by his sudden death. 6 years on and I am dating a fine gentleman who is 80 years old.I am 40 years old. He is an amazing guy. Each day we learn more about each other and grow closer together and deeper in commitment. I am uncertain as to marrying but we are doing as has been suggested… living each day and enjoying the moment…


Alberto April 20, 2008 at 9:00 am

I am an older man (55) who has just been in a 3 year relationship with a 33 year old single mom with a 6 year old girl. We are taking a time out as her Ex has been creating all sorts of problems.

I am divorced 8 years after a 25 year marriage. My mom, my dads 2nd wife and 10 years younger, enjoyed a great, tight, long marriage until they passed.

I saw first hand what a great marriage could be. I’ve tried to do this with this younger mom, but it has become very hard trying to instill my ideas.

The mom has to put her child 1st, her Ex 2nd, her job 3rd, her family 4th and then maybe me and the dog 5th. So after a hard day when she comes home angry and goes to kick the dog, she ends up kicking me.

I find the younger woman intoxicating but a tremendous amount of work which usually goes unappreciated. Being older I can tolerate it longer.
Most guys her age want no part of this world.
That is why the older guy works for her. He is just easier to deal with.

If woman would treat their man better and give him a higher status in their life, maybe life could be better for everybody.
Of course I might be sounding selfish.


lisa February 22, 2013 at 6:32 pm

I don’t think so. Older men do grow a patience that doesn’t exist at all with younger men. Its hard, though, to be at the bottom of the list. My kids are number one, at the same time that my older boyfriend is the same. Its so hard. I sympathize, but you desrve to be higher up on the scale. After a probably not so good marriage, you should be special and at the top of the list. Take care of yourself and your needs. Intoxicating is good, but its not unusual.


angela February 10, 2008 at 3:01 pm

hi i was in a similar situation with a man 20 years older than myself. I’m 40 and he’s 60.

Unfortunately i had to end the relationship because i didn’t feel able to trust him because of his life long infidelity record! but i fell in love with him ( probably why he had so many affairs – he’s a goodlooking, very fit, man with a wonderful personality!)
That was 3 months ago and i miss him so much! i wouldn’t have minded being his carer to the end if i had 10 years of love with him!

I say go for it, a good man is hard to find and if he makes you feel wonderful, what more can you ask!


Dr. J January 31, 2008 at 12:23 pm

Hello, all. May I look at this from a different angle–that of an older man? A single older man? A single older man dad? A single older man dad father of two boys ages 13 and 16?

So, here I am, 62, dad to two boys that could be, as referred to above, my grandchildren.

I am not ready to be out dating again and often wonder if I ever will be. My boys are my life right now, and I’m not sure I want to share that. At the same time #16 is looking to go away to college, and, tempus fugit, #13 ain’t far away.

Having given this age difference topic a lot of thought, I pose this dilemma: I don’t have a lot in common with women my age. For the previous decade and a half I have associated mostly with people 20 years my junior. The women have either done daycare to work or are now returning to their careers. My kids’ friend’s parents, the women with whom I work. These women interest me because we have a lifestyle in common. I’m just not ready for a geezerette.

In my late 20 ‘s and early 30’s I had a relationship of seven years with a woman about 20 years older (she never would admit true age.) She had 4 children, the oldest my age. We all got along great.

My older woman relationship eventually ended over the issue of the children that I wanted. It was particularly poignant when her grandchildren began to be born. It was another 13 years before my children came along.

I can relate to all the comments above about society’s reaction to significant age difference. I do think society becomes less critical or even observant once the junior partner reaches 40-45.

Unlike Amy, I’m not interested or looking. But, like Amy, this is a problem that disturbs me.

If I could borrow from Dickinson and paraphrase “Because I could not stop for Death, He kindly stopped for me.” Because I could not stop for Life, He will kindly stop for me. Sooner or later I will face Amy’s options. Don’t worry, be happy sounds pretty good


MikeyNMom January 25, 2008 at 11:27 am

i say go for it… i date older men the ooldest has been about 10 years older then me but in all reality 32 is still young… enjoy him!


VJ January 21, 2008 at 5:51 pm

Enjoying the moment seems to be the best option of the moment. It’s also a very good point to raise on relative health of our aging population. It’s something I’d add to my overly long comments, but it is a definite fact. Older folks today (say over the age of 50-60) are typically healthier today than they were a generation ago. Still, they are not usually healthier than those 20-30 years younger than themselves, Unless those folks do not have the advantage of access to good quality health care, which is of course a distinct possibility in some cases. But it’s good to hear some of the follow on details. Cheers & Good Luck, ‘VJ’


singlemomseeking January 21, 2008 at 10:04 am

Boomer: thanks for pointing out my typo! I wrote that post WAY past my bedtime. My friend is turning 34 this week. Yeah!


a. January 21, 2008 at 6:46 am

Hello all!

I am the friend that Rachel talked about. First off, she’s quite amazing herself–I love her blog and how she brings people together through it. Plus, she’s smart and gorgeous herself.

I read all your comments—I was quite amazed at how many people viewed 65 and up and unattractive—this seemed to be true in the past—but take a good look around people who are in their 50’s, 60’s and 70’s today–they are much healthier than they used to be—I look at both of my parents who are nearing the mid-60’s—my father has more energy than me–he stays up later, still is the life of the party and the last one to leave, plays tennis, travels—and my mother is an avid bike rider—she can beat me in this arena–she attends weekly to spinning class and LOVES it, has a body of a 40 year old—both are nowhere looking ugly or unattractive, are healthy and vibrant.

In addition, I was quite surprised by “she’s young gold digger” and he’s only looking for someone younger to make him look good. I’m a successful professional–pay my own mortgage (bought the house myself–no one helped me)—-pay for my daughter’s private school and morning nanny—and do not receive a single dime from her father—so I’m not looking for an older man with money.

He’s quite attractive, adventurous and fun to be with. I’m more concerned with what society and of course my parents think–which could be preventing me from enjoying our possible relationship. In addition, he did tell his kids about me–and they welcome the idea.

So, like Rachel suggested, I’m going to enjoy it for the moment. Thanks for all your feedback.



boomerzhx55 January 20, 2008 at 10:53 pm

Rachel, your single mom friend is 34 or 44 yrs old? If 44 yrs old, I think they are perfect match. Tell her to just enjoy the relationship. If not, over ten yrs old is great age gap. Anyhow, it depends.


VJ January 20, 2008 at 10:32 pm

Yeah, there’s the ‘ick’ factor too, which is one reason why people with disabilities have lower marriage rates (overall) and higher divorce rates. But again it’s hard to argue this. You either love the whole person, but more so for their ‘insides & brains’, for their functioning soul & humanity, or you’re generally looking for something else. Mostly, the typical person is always looking for that ever elusive ‘something else’. The hottest. The cutest. The biggest this, or with that lovely favorite shapely bit, and/or someone ‘who makes me tingle’, ‘takes my breath away’ or ‘looks just so scrumptious’.

Again this is the more familiar attraction & love style. It seems to suit most of us fairly well, in that it begets a continuing generation of children in reasonably good order while in our youth, and provides parents that are able to look after this young for the first few years of their lives. Before momma or daddy moves on to the ‘newest’ & better/younger/thinner new face that attracts them. Serial monogamy when & where necessary, perhaps mostly secret polyamory where possible.

They’ll always remain people who do not quite fit our preconceived notions of a ‘love object’. The comely gal in the wheelchair. That gamely gimpy disfigured young man who’s now a former motorcyclist. The old. And of course we’re all smarter than this, but our bodies and our limbic ‘lizzard’ brains sometimes know better. They know what they like. Universally we like the look and feel of youth. Everywhere. So why is it that slightly older single moms should not consider older available men? There are societal prejudices that surround each party, why not see if you might just get along? A question for the ages. Cheers & Good Luck! ‘VJ’


kb January 20, 2008 at 6:41 pm

I don’t have any issues with age, younger or older. There are times when I think it can get a little ridiculous and wonder what the two people could possibly have in common, but to each his own. It’s not my business.

Personally, I’m not attracted to men 20-30 years my senior. I’ve seen some great looking retired men, but I always revert back to my father and any possible attraction dissipates real fast!


VJ January 20, 2008 at 4:39 pm

As usual I’m supposed to be doing something else, but instead I’m thinking on this question.

The thing is that Jenny’s problem is a common perspective. And while not wholly wrong, it might need to be put in context. Is a ‘bird in hand worth several in the bush’? This is an age old rhetorical and even Economic question. How much is your time worth? Can you afford to take 5-7 years ‘out’ to enjoy several relationships that you may recognize ‘might not amount to much’ in the end? Sure, there’s much opportunity for mutual enjoyment and even friendship in these May-Sept.’ relationships. But to what end many will ask.

Have we ever wondered how all those classical rich, ‘dirty old men’ happen to wind up with those equally stereotypical young ‘gold-digger types’. They both took the measure of each other, knew the stakes involved, and went ahead with their plans despite the approbation of such an ‘arrangement’ by the general public & often the deep animosity of family. Often as not the couple represents in their own unique ways 2 lost souls in a loveless world. A younger woman who’s often seen for nothing beyond her beauty or ‘callow youth’ and without much prospects, and an older man who’s often just seen for his advanced age & infirmities, despite his past accomplishments. Is there love there? For many, they’d answer in the affirmative, with little hesitation. There also commonly is a comfort and security that the younger partner may never have been able to enjoy or experience previously. For the older gent, it may be the first time in decades he’s been able to enjoy the attention of an younger women, and one that is at turns attentive to his needs, without being in his direct employ.

But wait! What about Jenny’s realistic fear that “I would have ended up as a caretaker much sooner than I would have wanted.” Well this is simple and yet complex at the same time. As a Mom, you’re already a caregiver of course. As a Daughter, you have a better than 50% likelihood of being an Adult caregiver for another Adult family member before the age of 50 or so. Probably about a 70% chance of doing so by age 60 or so. There’s literally almost no escape of this hard reality. We sometimes live far too long as humans.

So it comes down to a very human Economic calculation that this lovely cuddly older guy before you is probably not going to last long in his present happy & healthy state. Strangely enough, this is a completely rational choice. Chances are, that you’re right. Sooner rather than later you’ll wind up taking care of him, and sooner than he might be taking care of you in a similar fashion.

Often love is not based on such coolly rational calculations. They’ve gone out of fashion almost everywhere, except in the twilight of life, for the odd, the overly strange, the poorly educated, the mis-educated, and of course for the ‘cripples’ & handicapped. But for everyone in the sunshine of their lives, in their prime late 20’s though mid 40’s, most people refuse to think about it much. Truth be told they may want to reflect on this cruel fact.

If you’re sitting in a large room filled with people, say a large ‘family style’ restaurant , you will be surrounded by people who are disabled or have severe issues with chronic diseases. Estimates vary, but we’re talking about 1:4 of everyone under the age of 35 and 1:3 above that age. Most are well hidden afflictions that people suffer from in silence, almost appearing normal. But they’re really not. They have higher rates of morbidity and mortality for almost every age cohort. Many also happen to suffer from being sometimes luckless & friendless in their adult relationships due to their limitations.

Now I say this as a happily married man. (This was once among the least common words on the internet, BTW). I know quite a few married couples. I know quite a few married couples where one or both spouses are severely afflicted by disease & are handicapped. Many of them were afflicted at young ages. In tragic car accidents (one while being parked), in sporting accidents, in shooting incidents, in wars. Most of these folks have suffered greatly, and yet the love remains and burns brightly. For the beautiful younger woman struck down with MS, now in the wheelchair, who had her ‘surprise’ change of life daughter who now helps push her up hills. For the older couple who can no longer drive, as he never did for decades, and she’s had too many brain surgeries to be safe now. For that youngish family almost broken by having several lovely severely autistic children who are loved so deeply that their entire lives are cared for moment by moment by their loving parents. Cross country, by caravan. While ‘Camping’.

Unfortunately aging and disability are a part of life. They can truly strike any family at any time. This is not a shame, it’s the human condition. We can run from it, we can hide from it, but eventually it will find almost all of us at inopportune times, and almost wholly or partially unprepared. We can choose not to gamble on such love & friendships. Or we can give into the ‘better angles of our nature’ and admit that yes, life can be a crap shoot, but this old so& so just might be worth it.

Like I said at the start, this is fundamentally an economic decision. How much is your time worth, really? How much is friendship & love worth? How long can love really last with disability? (Not uncommonly this is indeed a very foreshortened time). Statistics tell us that we are far more generous in spirit than we’re given credit for. But I wish more people realized this and appreciated it. Your life may very well depend on this in the future.

Just some very long winded thoughts here. Cheers & Good Luck! ‘VJ’


Jenny January 20, 2008 at 6:18 am

It seems that at one point I migrated toward older men. I want the stability and comfort that I did not find with my same age ex-husband. In one relationship the man was about 25 years my senior the other 30 years my senior. I ended up not allowing either relationship to develop b/c of three reasons. The first, fear that his children (who were my age and older) would strongly disapprove. Second, I also feared that b/c both men were very well off that I might be perceived as a gold digger. Third, being 34 at the time, I would have ended up as a caretaker much sooner than I would have wanted. Our time together would realistically only have been a short time.
I feel that maybe if I had been really in love all these issues would not have mattered but they did and so I ended both. Now I am in a relationship with a man who is my age and he is stable and secure. I realized that I do not have to look for an older man to find these qualities. I just have to look for the right person, regardless of age.


Ms Single Mama January 19, 2008 at 8:04 pm

She should enjoy herself. We, as single mothers, have this weight – thinking we can only date men if they’re marriage material. Sometimes we just need a nice guy to pamper us – tell her to just go with the flow and follow her heart. Sounds like he’s worth a try.

I dated a man who was 10 years older than me (he was 38). It was just like any other relationship I’d been in – the age difference really wasn’t the issue. Right now I’m wtih a younger man … once again, age really isn’t an issue – it’s who you are inside…


Susan January 19, 2008 at 6:07 pm

You know, I think at a certain point ages kind of smoosh together (not the technical term!) Since becoming single again (at 34, I’m now 39), I’ve routinely gone out with guys who are older than me, although admittedly the largest age difference was 11 years. I would say to your friend: go out, enjoy each other’s company and see where it goes — if anywhere. 20 years is certainly a big enough number, but after a certain age I think it really depends on the individuals and how they are as a couple.


butrflymom January 19, 2008 at 8:14 am

I have to agree with you Rachel. I passed an opprotunity to date a man 20 years older who is a great guy and a good friend. And even one who was 13 years older.

It seemed that in both cases we were in different places in life, they were retiring and had already gone through the “teenage” phase. I don’t feel ready for “retirement” and am even back in school to change direction.

Not to say that it will happen, but the chances of having to take care of an aging partner are huge.

I’m still seeking a partner in the 40s or early 50s now but mostly concentrating on school and my teenager. seems to keep me busy enough.


Single Parent Dating January 19, 2008 at 6:11 am

I have to agree with the fact that she should peek into her crystal ball 10-15 years from now. Especially considering her daughter. Her teenage daughter would have a potential step father who would be old enough to be her grandfather. You just can’t neglect that angle either.

Single Parent Dating



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