Dear  Matchmaker Rabbi:
I’m 43 years old, recently divorced, and have joined Jdate after being out of the dating scene for over a decade. A man wrote me recently who is very attractive, has a great bio and was very warm and personable in his e-mail. But I was totally taken aback to see that although he is 45 years old, he has listed his desired age range as 28-40. Twenty-eight! I can’t believe it! What person in their 40s would want to date a 28-year-old?!? One part of me wants to write him back but the other part is totally hung up about this. I’m equally annoyed he only wants to date someone younger than himself, not older. It’s just so hypocritical. What do you think?

— Stumped in Philly

Dear Stumped:

I don’t blame you for being annoyed. There was nothing I found more annoying during my years of dating than all the guys who were looking for women younger than themselves — sometimes even much younger — and who were unwilling to date someone even 3 or 5 years older. It’s not just hypocritical, it’s vain and even sexist.

That said, you should really try not to disqualify someone for one tiny detail written in their profile that you don’t like. You never know the back story. Maybe he filled it out without really thinking about it. Maybe he really would date someone older, if it were the right someone, and he just hasn’t been faced with that situation.

And, while I agree that a 17-year age difference would potentially create many problems in a relationship — different maturity levels, life goals, energy levels, etc. — this, too, is impossible to generalize. Some people are able to create happy life partnerships despite big age differences (look at Calista Flockhart and Harrison Ford; or Demi Moore and Ashton Kutcher). So, while most 45-year-olds are totally ill-matched for most 28-year-olds, that’s just a generalization too.

Don’t be too quick to judge. If everything else is a “go” — give this guy a chance. Worse comes to worse, you’ll have a nice night out on the town.

— The Matchmaker Rabbi

To ask The Matchmaker Rabbi a question, please email

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now in her fourth year of rabbinical school and the mother of 1.5 kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating adventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. You can follow her on Twitter at @wanderinghebrew.

  1. Men do like younger women. One solution to this “problem” is to force all men on earth to be attracted to women their own age. Some solution! Indeed it is women that have invented this egalitarian fiction that says that that both genders are identical, inspite of all experiential evidence to the contrary. Your flaw is easy to spot: Equality-Of-The-Sexes does not mean Identical-ity: it means equal respect.

    What is worse is a Movement that convinces women they should be dating men their own age whereas a women can be much happier with a man much much older than she. You should be considering men up to 1/3 older than yourself, and never younger. There is nothing better for a younger woman than to date a man with more experience, wealth and power.

    Try it. You will love it.

  2. A man who is interested in dating much younger women is usually insecure and is ashamed of his own age. I noticed that quite often this type of men is also misstating their own age by a few years. Being a woman, I never find such men attractive. When someone who is much older than me is contacting me and hinting at his young looks and financial stability, it tells me that most likely he is someone who is unhappy with himself and wants to bring up his own self-esteem by being associated with a younger woman. I find such men unattractive.

    There are of course different flavors in that category. For example, my 32-year old friend was asked out on a date by a 38-year old guy. After a few so-so dates, she decided to introduce him to her friends and see what we think of him. It took us less than half an hour to figure out his actual age of 44. His math just didn’t add up to 38. He later admitted to her that he was indeed 44, but felt that he looked like 38. By the way, he actually looked like mid 40’s.

    Another example. A man who was older than my parents reached out to me and asked for a date. I was shocked and replied that I am not interested and asked him if he tried dating people his own age. He replied that unfortunately, he didn’t find women his age attractive. That was coming from a man who was ashamed to show his real looks and in his profile picture was hiding the top of his head under a motorcycle helmet. Speaking about being delusional.

    And yet another example. I had a date with a guy who was 6 years older than me. The age difference was fine, especially since his profile specified a large range of women’s ages, including a few years older than him. When we met in person his math didn’t add up either, he was actually 10 years older than me. He also told me that despite the desired age range in his profile, he is looking for women much younger than him, because he wants to show his ex-wife that he can have kids right away and to cut down on his alimony. I thought it was revolting, but I tried to keep my cool. He didn’t stop at that. I guess he thought that I was still interested. He leaned closer to me, and whispered in my ear that he had a test done, and since his sperm count is of a donor grade, he’ll be able to knock me up in no time. I couldn’t get out of there fast enough!

  3. When women is complaining abou this ” issue” where men prefer women younger its mainly older women who is somwhat dissapointed with not being approached as much as before ( as in their younger years). How can you now abou the possible happiness of a couple with some age difference. I feel just like gueesin and assuming when I read some of your comments. Anyhow, if a man is lets say 40 years old and wants to have a family i wold say its very natural to look for a woman between 25 and 35.

  4. Um, the biological clocks are about 5 to 10 years out of sync so whatever political beliefs you hold, get the facts. Dating is often about having kids and doing so safely and responsibly. Keep your personal views separate from the science. 20 years is a separate issue, but not willing to date older makes a lot of sense for a guy in his 30s.

  5. Wow Paul, you somehow feel it to put quotes around a real “problem” but then force your own opinion on a new generation of women to not date their own age. I’m 26 and I’m repulsed when people who are old enough to be my father somehow not only hit on me but have age ranges that go even lower. And let’s not talk about 29-30 year olds that have age ranges that stop at 25. Whenever I see that on a profile I don’t even bother to respond out of principle. Yes, if I was more desperate I probably would overlook that. But for now it’s a total turn-off. I personally wouldn’t pursue someone who is more than 5 years older or younger.

  6. I am 56, and attracted to younger women (35-49) for several reasons, none of which is being ‘ashamed of my age’. Younger women are more fun. They are not as focused on the negatives of being single. They are more sexually open, and are willing to allow a relationship to organically evolve. They generally are less bitter about their divorces, and have much more positive outlooks.

    And yes – they make me feel more alive and in touch with my younger self.

    Men who like younger women are not evil. They simply want to be happy, and be in relationships that make them feel good.

    It’s a lot simpler to understand than most people think.

  7. What bothers me about older men is not that they want to date younger women, but rather they seem to assume that younger women want to date them. With few exceptions, we don’t!

    Go ahead and ignore women your own age, that’s your business, but don’t get mad when you can’t get any younger women. The men who complain the loudest about women they own age are the very same ones who are outraged that younger women don’t like them. Maybe we want a partner with whom we can build a life, not a AARP member.

    Guess what? You haven’t aged any better than the women your age. Get over yourselves!

  8. Oh dear, Paul Sheer!
    How wrong you are. Most younger women I know are repulsed by older men who they find creepy and rather sad.
    Why should women date men ‘much much older’ than them? Women in their forties and fifties want good sex and fun, they certainly don’t want to be spoon-feeding a dribbling wreck! I’m sorry to have to tell you that most women I know are dating men on average 5 years younger (and some the same age as themselves, I grant you) -and they are very happy.

  9. I am a man in his 30’s. It is completely normal and natural for men to date younger and for women to date older men.

    First of all, women mature faster than men and tend to look more physically “mature” faster, as well.

    What about me dating an older woman? I have a mental block against it. I can’t help it. Have I done it? Yes, sure when I was a teen ager at 17 or 18 dating a 25 yr old or at 20 in France dating a woman who turned out to be 31 or 33. But I couldn’t have ever married them. It would be upside down.

    For all of history (and probably pre-history) up until recently it was quite common for there to be a 12 to 20 year difference between husband and wife. Were their still some couples with similar ages? Sure, if they met both young in the teens or say 21 at university.

    In this decade and the last their has been a propagandistic backlash as if this were somehow perverse. Women if not braninwashed/influenced by this recent “wave” feel better usually with a man with a little more experience and wisdom in life. As long as they are not infirm b/c of their age; so be it. Furthermore, Rabbis say that an age difference in their opinion of up to around 10+ or – yrs is not critical.

    Unfortunately, initial physical attraction is a necessity in the first stage. I am guilty as well. Honestly, most women who are my exact age I find difficult to be attracted to ( so it is not just the “number”). I can’t help that. That is how I am wired.

    I want someone I am attracted to at least in the beginning and then we can grow old together. Also of prime importance is that i wish to have a family or at least 3 children maybe 4+.

    I don’t understand where some frigid women here say that an older guy approaching them is disgusting or off-putting. If for those women they did not know the age but were physically attracted to the gentlemen and then build something for profound, why should it matter? After all this is biologically normal.

    As my late bubbe/safta Rikki z”l (may her memory be for a blessing!) used to say, “age is just a number.” Ladies as long as you are relatively attracted to the would-be courter don;t let age get in the way.

  10. I am a 28 year old woman, and i would say that i would prefer to date guys who are at least 6yrs older than me. I would probably say that the happiest relationship i was ever in was with a man who was 18 years my senior.

    I agree with Jacob, men who want to start a family have to date a woman who is still capable of having children, it’s unfair, but a 45 year old man can still father children whereas a 45 yr old woman, could probably not do so easily if at all.

    Furthermore, its not creepy or disgusting, its natural and the way the world has evolved over centuries. I think the women who have posted on this topic have their heads in the sky. Older guys i believe make a better fit, i think that the age gap actually compliments each of the sexes.

  11. To Jacob and Eric and Rob, etc,
    Older women do not find older men attractive either. I am in my late 40’s and the men in their 50’s for the most part are over the hill for me and I am not at all attracted to them. Like Livvy said, women in their 40’s and 50’s want good sex too and it is hard to find men in that age range that can still have a good time. Just as I know it is unlikely that I will find a younger man, older men need to realize it too. We’d all like to look like we did at age 30 but most know better that we must grow up and move on and find ways to connect with people our own age. I see so many posts of these men who are in their 50’s who have played around and NOW want a family so they are looking for girls in their 30’s. Good luck. And once you find you can’t get one, look again at the women your own age and realize we have alot to offer. We both have to compromise.

  12. All this whining because men like sexy young women is a waste of breath. Do you think you’re gonna change that?
    I didn’t think that 43 year olds suffered from dimentia.

    Look, you’re 43, so for a serious relationship, date a guy who’s 63.
    Problem solved.

    Or, for a sexual relationship, find a few 20-somethings and become a cougar.
    Problem solved.

  13. I dated a guy that was a year older than me and I felt like I was his mother…all he ever did was play playstation games while I was taking care of him and our home and working on top of it…he ended up hurting me really badly as well and that’s when I decided to date an older man…I am 23 and my partner is 41 and I couldn’t be happier…he is everything I could have asked for and so much more…age is just a number and if two people want to be together then nothing should stop them from being happy.

  14. @OLD MEN,face it you are old and disgusting!!u think you look great?no,u in my 20s and i would rather date a younger man(10yrs younger when am 30s) than an older man.eeeeew!i thank Godess for feminism:D.amen!!…i would disown my dad if he did that to my mom

  15. atleast i will give you one thing:their(usually) after your money and not you.

  16. The thing I love is this much older men are looking for much younger woman, saying they are firmer bodies, etc. But have you seen the going trend in the United States. Obesity is an epidemic.

    I’m in my 30’s and I am very active. Most men in their late to early forties can even keep up with me. Why would I ever want someone much older than that?

    Most men that are looking for much younger are delusional. The chances of the these much older men finding a much younger woman is very slim. Only 1 percent for 20 plus years difference turns into marriage or serious relationship. Pretty bad odds. 8 percent for 10 plus years difference, still really bad odds. So all this talk about a much older man getting a much younger woman, is stupid. Most of these men troll on dating sites hitting on everyone on the site or off the site, until someone says yes, but most likely this woman is got daddy issues, or other issues. Most older men that date much younger women aren’t any more mature! I seen some very immature men in the 50s and 60s!

    And Paul you are truly clueless. You are probably one of these single guys for many years still holding out for your much younger trophy woman that will never appear. Women also have to be attracted to them man they are dating. Some women may overlook this due to money or etc. But would you really want a woman to not be attracted to you but your money. Really sad.

    Women should not have to ever settle, and by dating someone more than 7 years older and especially 10 plus years and so on, is settling in some way. Yes there are unique circumstances that couples find love with big age differences, but does anyone look in the future? So a 20 something woman marries a 50 something man, his life expentency will be around 73 years. So, she could be a widow in her late thirties. How is this even fair to her. Or even worse she becomes a nurse maid for many years. Gives up her life for what and older man when she could be dating someone her own age and have better odds with everything!!!!Men need to man up and get their priorities in order.

    I know about 10 men that have been on dating sites for 5 plus years that wont even consider a woman their own ages. So why they sit and wait for the trophy ego boast they continue to be lonely, I bet even in 5 years they will be doing the same thing! Yes they may get a date or two but the odds turning into anything serious is soo slim.

    Most men I have seen in their 40s 50s and 60s are gross! Yes there are some that have age well and take care of themselves but all the other stuff previously stated comes into play.

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