Is It Creepy That My Boyfriend Slept With A Much Older Woman And Thinks That’s Okay?

Boyfriend Slept With A Much Older Woman

My boyfriend is 24 and I am 19, and we have been dating for 10 months. A while back I found out that he had hooked up with a 40-something year old woman when he was 21, in a “friends with benefits” type situation. They never dated, and I’m not sure how long this went on but it ended when she moved to Ohio (my boyfriend and I live in Pennsylvania). He said that they never dated, neither person was cheating on anyone else, and it was a purely physical relationship.

It’s not the fact that my boyfriend had this relationship that bothers me. What bothers me is that he doesn’t think it was a mistake, he doesn’t regret it, and doesn’t think there is anything creepy about the age difference when it comes to who you sleep with. He does have a rule in the age gap for people he dates, but not with whom he sleeps with unless they are much younger than him.

He keeps trying to understand why I think it is creepy, but I can’t explain why because it just seems self-evident, especially when you consider that the woman’s child was older than him. And that she slept with someone younger than her own child. It just really bothers me that my boyfriend doesn’t find that weird.

My boyfriend thinks that the reason I care about it is because I feel inferior to that woman since she is much older and would have more sexual experience than I do (I was a virgin when I met my boyfriend), but I don’t really feel like that’s what my problem is.

I don’t know what my problem is actually, and that’s my question. Is it reasonable that I would find this creepy? If not, why do I find it creepy? Is there another way I can think about it so I can get over this feeling?


Once upon a time I had a male client who was very judgmental when he found out that his girlfriend participated in a threesome with two men. While he loved the idea that she was sexually adventurous, he couldn’t get the image of fingercuffs out of his head. I pointed out to him that he had seen a number of prostitutes, and that, if we were to be objective, his behavior can only be seen as equally questionable.

I just think that you — like most of us — are judgmental of things that you can’t understand, haven’t experienced, or wouldn’t want to experience.

He hemmed and hawed and tried to justify it, but he couldn’t wrap himself around his own hypocrisy. He held the deep-seated belief that men can do what they want, but if women do what they want, they’re slutty. The real truth is that we should all be entitled to our secrets. Presuming he’s clean, he shouldn’t tell her about the hookers, and if she knows that men can’t handle the image of their girlfriend being double-teamed, she should probably keep that one to herself.

The real issue here, Zoe, isn’t your boyfriend’s FWB relationship with an older woman. Hell, that’s a fantasy for most guys. It’s really about your feelings about it and what you’re making it mean.

But you already knew that. You said that you don’t even know what your own problem is, as if I’m going to be able to tell you. I can’t. I’ve heard some crazy shit on this blog over 7 years and your boyfriend’s cougar affair is nowhere near the top of the list. I just think that you — like most of us — are judgmental of things that you can’t understand, haven’t experienced, or wouldn’t want to experience.

Nowhere is this more apparent than in the realm of sex.

Don’t worry, Plushies and Pony Players, we’re cool.

I find it hard not to be a little judgmental of people who participate in alternative sex acts. When my wife and I went to the Museum of Sex in New York, there was an exhibit on kink, and we were shocked to find out just how vanilla we were, in the grand scheme of things. But, like any prejudiced belief, it’s intellectually easy to overcome. Just because I don’t want to do something doesn’t mean someone else can’t take pleasure out of it. And if no one is getting hurt, far be it from me to deprive someone of his/her kinky sexual enjoyment.

You’re just really confused because of two reasons: a) you’re young and extremely inexperienced, and b) you would never sleep with a man twenty years older.

You’re just really confused because of two reasons: a) you’re young and extremely inexperienced, and b) you would never sleep with a man twenty years older. Because your loving boyfriend did, you’re experiencing some cognitive dissonance. But I’m telling you — as a guy who once had sex with a woman 15 years older, it is certainly not creepy, deviant, or reflective of his ability to be a great partner. Stop judging your boyfriend for having more experience and finding older women attractive and you’ll be fine.

And, one day, believe it or not, you’re going to learn that 40 isn’t very old at all.

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  1. 1

    This post made me giggle due to the shear naivety. Good for the 21 and 40 year-old! As an older woman myself (52), given the chance, I’d be all over it.

    1. 1.1
      Lynn (the other one!)

      *g* My thoughts exactly. Whoo ha! (I’m 56).

      1. 1.1.1

        I am a woman in her forties dating a much younger man in his late twenties.   I continue to be surprised at the sheer numbers of   20-21 year old fellow who hit on me.

        And yet….       I can also identify with the letter-writer.   When I was just 19, my then 21 year old boyfriend dumped me or his friend’s mom… who may have been 41 or even older.    I was so disgusted. especially when my boyfriend describe how in love he was  and that she was a really beautiful woman who really understood him.   All I saw was someone’s old mom.    We I was out partying at bars, I would see her surrounded by young men.   I was like “they are all disgusting”      “why doesn’t she grow up?”.   What I did not understand is that she probably was also dating men her own age, earlier in the evening and then partying with the young ones when the fifty year old went to sleep at 9:30!     

        Paradigm shift is correct. Once you have been divorced, you look at divorced people differently.   Once you have a child, you realize your old ideas about parenting were wrong.   Once you lose a parent or a peer to death,   you cross a river of understanding.   Once you are midlife, you look back and laugh at the judgemental teen you were.

        1. Garret

          I continue to be surprised at the sheer numbers of 20-21 year old fellow who hit on me.

          For the life of me, I will never understand why women find this surprising. Having a sexual affair with an older woman is on every young man’s “before I turn 30 bucket list.” I think women simply don’t understand men. I think it comes from how selective women are, even where having no strings attached sex comes into play. For women, NSA sex is usually with a guy they see as totally hot, but for one reason or another, he is not long term relationship material.

          Men are simply far less picky. Amazingly less picky when it comes to having sex. Men will have sex with a woman who might make a great wife, who is a great person, but also a woman who is not up to what he wants long term. Seriously, have women never heard of “whale hunts.” It’s where a group of guys literally have a contest to see who can have sex with the fattest woman that night. I myself have never done that, but I will admit that I had sex with women I was not totally turned on by. Decent looking, or OK looking, but not up to what I wanted long term. The women I entered into long term relationships with the hopes of it leading to marriage were not the same. They were better looking, younger, etc…

          Dating an older woman has a benefit that comes along with it. She is typically better looking than the younger girls we have no strings attached sex with. She has kept herself in shape, or worked hard to get back in shape, so why not have sex with her? But he is also doing math in his head. “She’s 40, I’m 22, so when I’m 32, she will be 50, and when I’m 42, he will be 60. OK, be ready to bail when she won’t play the waiting game anymore.” In short, he knows that father time is catching up to you fast, so he isn’t in it for the long haul.

          Another thing is that men don’t always say what they mean. She understands me is easily interpreted to, “She took me home and screwed my brains out without all the drama, and jumping through hoops.” See, women love to say that it is their confidence that attracts younger men. BS. That’s about as true as icebergs forming at the equator. He’s attracted to you because you are the path of least resistance.

          Other reasons younger guys date older women are her money, to gain experience, she will have sex without pushing for a long term relationship or requiring a lot from him, she shows that she is hugely attracted to him while the young women his age are all still trying to get that top 10% of guys and so aren’t looking at him with the same focus as older women will.

          My advice would be no different than Evan’s. Have a ton of fun, if fun is all you are after. Live it up. Why not? But, if you are intent on marrying a very young guy, mentally prepare yourself for a major letdown.

          Also, 50 year old guys likely have serious jobs that require them to get up at 5 or 6 in the morning, same as us 30 somethings. Funny how that alters the time you need to go to bed. The college kid likely has his schedule such that he often doesn’t have to be up early in the morning. I know many guys who wouldn’t take a class before noon if they could help it.

          If you are talking about Friday or Saturday night, I think you are just having fun with stereotypes because the 50+ men I know often stay up well past midnight if they don’t have work the next day.

      2. 1.1.2

        I’d hook up with yah.

      3. 1.1.3

        Mmm 😉

      4. 1.1.4

        i love older woman!

    2. 1.2


      Oh, and to be sure, when she is 41, if she is single, and a 21 year old guy hits on her she likely will no longer see an issue with it, and she too will be all over it. The question is, when you were 21, would you have been open to hooking up with a 41 year old guy?

      I think it is far more likely for young guys to be willing to hook up with much much older women than it is for young girls to hook up with much much older men, because young men see sex as recreational if it is outside of a prospective long term relationship. Younger women are still in that “got to find THE one,” mode. So they are extremely picky. Men and women are often so very different when it comes to some things and sex is one of them. I can’t even tell you how many times women have told me that if they are going to have an affair, the guy has to be totally fine. Men on the other hand will often have an affair with a woman who is far below what he is willing to date. How many times have you heard a woman act incredulous that the man cheated on her with a woman that is not attractive. And OH boy do women take that wrong. It stings their self esteem because the view an affair from their perspective…so in their mind, if her boyfriend or husband is going to have an affair, they expect that he did so because the woman is higher quality than her. So when they see that the woman is not attractive at all, they wonder what he thinks of her, his wife or girlfriend. In other words, “if he is going to have an affair with that cow I must not be very special.”

      OK, anyway, I think EMK nailed it. I think it is as simple as the fact that this 19 year old girl sees older men as creepy. She’s going to be amazed at how fast the next 22 years goes by and she too will be “old” and as EMK says, she will then learn that it’s really not that old.

      In other words, she has a paradigm problem and needs a paradigm shift. Likely to happen? I doubt it. It is likely that she has several older people in her life, from Grandpa, to Uncles to Teachers, to coaches, to neighbors and or parents of a friend. It is also likely that some of those older men are not very young at heart and are not stylish anymore. Like that old guy who wears pants an d shirts that went out of style 30 years ago, and he has a musty smell. This will color her opinion until one day, a cool older guy will present himself to her at just the right time, and she will learn it is about the individual. Just like I could judge all young women her age based on some very skanky 18-22 yer old women I have known.

    3. 1.3

      I am over 50, divorced, and only date guys in their 20s and 30s – I am not at all attracted to men my own age/older. I couldn’t get the younger guys, I would choose to remain celibate.

      1. 1.3.1

        This is nice to read. I am almost 50 and had a brief thing with a guy who is 28 who still texts me to flirt all the time, though me being sensitive and too easily attached through sex, that’s all I can deal with. He seems intimidated by me anyway, so it’s all good. I don’t think he realizes how old I am as I am one of those who keeps in shape and takes care of herself.

        But I like the attraction and innocent flirtation we have with one another still. I wish I could have no strings attached sex, but it doesn’t work for me and it’s taken me this long to figure it out. But he’s sweet and we have hung out once since and he talks about coming to visit me. (He lives a few hours away.) On the other hand, since I don’t expect anything to go anywhere with such a younger man, maybe it’s the perfect thing for me if I can let it just be what it is. An older female friend of mine told me I should take advantage of it while I can.

        I tried dating older men in my early to mid 40’s.   A dated a man in his late 50’s and recently tried dating one who was 68, but seemed and acted more like late 50’s and honestly, the whole thing grossed me out. I couldn’t keep up a physical attraction, even though he had sexy energy for his age.

        I found these guys misogynistic on some level as well with a lot of baggage they never dealt with. And they think they have all the time in the world to attract younger women. One of them finally figured out he needed to get back in the shape as is doing it now and the older one still thinks he is fit to get women younger than me. I was actually “older” for him to date.

      2. 1.3.2

        Good to her that

    4. 1.4

      I think the women that are calling dating younger men gross are women that are not decent looking enough to get a younger man. Can you say jealousy?  

      1. 1.4.1

        For me, personally, at 33 it has less to do with being hot enough to date younger guys, it has everything to do with wanting to date a man who is on a similar timeline. A 21 year old man is probably pretty disinterest with having a stable income and getting married and having a child in the next 2-3 years. And personally, I’ve always found in their mid-late 30 thirties the most attractive.

    5. 1.5

      Move over young girls…. You’ve got older hot women coming into your arena that guys are more than happy to experience.   We’re not bugging them for love or playing games.   Never underestimate the overwhelming sexual energy between a young male and an older woman !

      1. 1.5.1

        Very true! I had a thing with a younger guy (by 20 years) that has turned into an ongoing flirtation and friendship. I really would not even think of putting expectations on him if we end up together again more intimately, though I would maybe around someone more my age. So maybe it works out well!

  2. 2

    Judgement of others often comes from fear.

    My sense is that the writer of this letter feels insecure that her partner was with an experienced person before he was with her (age is just a detail- it’s all about the other woman’s experience). The letter-writer is afraid she doesn’t match up. This may be why she is asking for insights – because it is uncomfortable to face it.

    A good way to get over ‘this feeling’ is to work on one’s own self-esteem and understand that our worth may be far better measured by how we face situations (ie. as Evan suggests above), than by the past situations themselves, which we can do nothing about.

    1. 2.1

      Could be that she’s too young to fathom that certain people are actually persons and not objects.

      Her: I’m an object for my boyfriend. Sexy, etc. etc., but he better never treat me like one. Boyfriend is older, mature, a man. My guy.

      Suddenly….omg. what? boyfriend is a person who lived a little before me. eeww. what? what? wait? he did it with who??? an OBJECT that was OLD—ER??? Whyyyyy?       (her boyfriend’s view: it’s no big deal really, just a couple of people having sex. what gives?)

      Didn’t sink in yet that most people really are human beings or persons. That might occur when he’s about 27/28.   “Oh. Oh. Oh yeah, um, that’s right, well, mom’s a person. dad’ a person. yeah..ya know, they’re people.”

      something like that.    So…embrace your boyfriend for actually recognizing that a lady is a PERSON and not a mere object. because with that, he probably views you as person, too. And that’s a good thing.


      1. 2.1.1

        Correction:   Didn’t sink in yet that most people really are human beings or persons. That might occur when he’s about 27/28.     should state *  she’s*

        when she’s about 27/28

      2. 2.1.2

        I would say that this is a possibility, but what is more likely is that she is simply one of those girls who thinks dating/marriage is creepy unless the two people are very close in age.   These are the type of girls that would claim even a very top shelf man, who flirts with her, or shows interest, is creepy because he is well outside of her very narrow age range that she sees as appropriate.   The man could be the furthest thing from creepy and this label has nothing to do with him, and everything to do with her own personal perception.   Not all young women are like that, and even fewer young men are like that, at least not where dating and sex are concerned because while the vast majority of young men aren’t interested in marrying a woman even 4 or 5 years older, they have zero hesitation when it comes to dating, having sex, and even shacking up for a while with a woman who is much older…even 20 years or more.   It’s only when they look at making it permanent that age seems to matter to them.


        I also doubt that being 27/28 will alter her ideas much about dating/having sex with much older people, though as she gets older and older, I suspect that she won’t see it the same way, in reverse.   She will likely have little problems dating much younger men.   For her, it is the other person being older that is the problem.   It’s creepy to her, which as I said, is all about her perceptions.

  3. 3

    I don’t think it is about experience. It sounds to me she finds it a little on the creepy side because in her mind she somehow links it to pedophilia where the woman is the adult and her boyfriend was a child. It may be because at her tender age of 19 she is yet to realise herself as a fully grown woman and so has projected that perceived adolescence onto her boyfriend. She needs to keep reminding herself that at 21 he was no longer a boy but a man.

  4. 4
    Erin DeLear

    As a woman over 35 who’s been with younger men….nope. Not creepy at all.
    As to why younger men like the thought of an older woman, I really can’t speak for them at all.
    However, what I do know is that it’s not about how much experience you have, but rather attitude and self confidence.

    I have heard from 20-something guys that they have a certain level of frustration with the girls they date because the girls always seem to be overly self conscious when it comes to sex. They seem to be unsure of what to do, feel awkward talking about likes/dislikes, worry about the size of their thighs or boobs, if they are making too much noise or not enough noise…etc, etc.
    All the uncertainty takes away from the enjoyment and takes you out of the moment.

    So in the end it’s not about competing with women that have more experience or feeling that you’re lacking in any way.
    It’s about learning more about yourself and growing into your sexuality I think.

    1. 4.1

      I feel really bad for very young women these days. They’ve been brought up with porn so easily accessible since they were young. If you think sex is supposed to be like porn and that women are supposed to look like porn stars, you might be a bit self conscious yourself.

  5. 5

    Hmmm….I wonder how this could be creepy? Two consenting adults …. and we know that women only really come into their sexual prime in their late 20s anyway. I have had partners of all ages and I am in my early 30s. The latest one is a man in his late 60s and it’s the best sex of my life. What can I say? It’s all in the mind.

  6. 6

    I can totally relate to how this young woman feels!! I recently turned 25, and until about a year ago, I thought people who had sexual/romantic relationships that had significant age disparity were way freaky. When I thought of people over the age of say, 30 or so I imagined my friends’ moms and dads, my own parents, my therapist, my doctor, and other such authority figures. When you are young, it can be hard to imagine your elders as real people with their own inner lives, needs, desires, fantasies, and feelings. It’s like seeing a teacher outside of school, completely weird and awkward! However, last year I befriended and eventually started dating a man who was 50. One of the biggest shockers about the relationship for me is the fact that a 50-year-old man is so totally a complex human being and more like myself than I thought. I’ve learned that life absolutely does not stop just because you’re over a certain age. Perhaps I’ve been naive, but this has opened up my eyes so much. I see people so differently now. I think this young woman might still be seeing life through the eyes of a child in many ways. Also, on a funny note, I used to work at a nursing home as a CNA, and I had one resident who was in her late 80s. On days she felt good, she would roll out of bed and say, “I feel 40-years-old today!” At 22, I found this mildly horrifying. I was like 40?? That cannot be good!! Now, a few years older and a bit more experienced, I’ve learned, as Evan said, 40 isn’t that old at all.

    1. 6.1

      “Perhaps I’ve been naive”….

      Sweetheart, that is the understatement of the year.

      I’m still reeling over how you were shocked that you met a 50 yr old who was “so totally a complex human being”. Did you think it was the teenagers & 20 somethings that were the most complex? They haven’t even begun to live life yet!

      I have often wondered if we should be worried about the future of our civilization with how silly young people sound these days, no need to wonder anymore…everyone, we’re screwed & not in a good way.

  7. 7

    Looks like I’m the weird one yet again. I’ve had ample opportunity to hook up with 20-somethings (I’m 45) but I have absolutely no interest. Might be because I am a mother of a 21 year old. I guess if that’s your thing. more power to you. I would just feel extremely awkward.

  8. 8

    I’m 44 and, like Starthrower68, have no desire to get with any 20-something.  
    I think the Letter Writer needs to stop trying to figure out *why* she’s creeped out by her boyfriend’s experience and simply decide to let it go.  
    For many years, I was with a fellow whose only major relationship, before me, had been as “the other guy” for an engaged woman.   In other words, he had spent more than a year in love with a woman who was cheating on her fiance with him.    I found (still find) that icky; he wasn’t the one who’d cheated but I didn’t think that being someone’s “sidepiece” was noble, either.     However, I realised that I could either 1. allow a choice he’d made years previous to poison our happy, loving relationship or 2. accept that we all make mistakes, be aware that he might have issues with his moral compass (as it turns out, he was a devoted and honourable boyfriend to me for many years) and just. drop. it.    I glad that I went with the second option.
    @ Letter Writer: Please stop with the analysis.   It’s damaging the bond that you share with your boyfriend.   Whether sleeping with an older woman is creepy or not is beside the point.   Either accept your beau (and that includes the past that has made him the great guy he is today) or break up with him.

  9. 9

    Well in now days this is common to date and older women and other stuff also.. I have shown many guys who like to date older women.. so every person has their own choice so I think its not bad thing..I know most of girls are not agree with my opinion but this is my thinking point of view…

  10. 10
    Karmic Equation

    @Starthrower & Henriette,

    I’m 47. I went on a date with a 33 yo during the summer. He was a very young 33. Didn’t have much life experience, still lived at home, to save money to buy a house. He got preapproved for buying a house the day before we went out (I found this out during the date). So while he was more responsible and financially stable than many men his age, his lack of life experience was a huge gap between us.

    On the other hand, I’m currently dating a 30-yo fitness trainer who’s been on his own since 21 and has been a fitness trainer since 21. So while young in age, he has tons more experience in his industry than men older than he. He has owned his own business since he was 25. He’s even more responsible than the 33 yo, a little less financially stable due to being an entrepreneur although his business is starting to take off. But due to being a business owner for so long, he’s got life experience and is responsible far beyond his years. He still indulges in b&w thinking, which is a sign of immaturity imo, because as you age, you realize that life is one big grey area 🙂 — He and I are so compatible it’s a little disconcerting. If it weren’t for the huge age difference between us, we’d be in a serious relationship instead of a casual one.

    I have many male friends, in their early 40’s and will into their 60’s, who struggle holding down an FT job, and who are far less mature than either the 33 yo and 30 yo in terms of financial stability and being responsible.

    So age shouldn’t really be the reason you don’t date 20-somethings (or 30-somethings) — It should be whether you and they are compatible in personality and temperament, and whether they have the life experience to mature them beyond their years. At the same time you have to young enough at heart to keep up with — and tolerate — their joie de vivre. And you have to be wise enough to know that the relationship will be temporary.

    Of course, most men in their 20’s and 30’s aren’t looking to settle down. THAT would a good reason to not date them if YOU’re looking to settle down.

    That said, I would HIGHLY recommend dating a 20-something or 30-something as rebounds 🙂 If you date a 20/30-something, you do have go into it making sure you have the self-control to NOT allow yourself to fall in love with them. I love my trainer and he loves me (we’ve traded the l-words many times now) — but I’m never going to allow myself to fall in love with him. That would be emotional suicide.

    If what you want is love, you can find that anywhere, provided you’re willing to make some tradeoffs. If you’re looking for security that can only be found in a relationship, then you might be trading off on love experiences, that can enrich your life, even if temporarily.

    If you’re really looking for love, let go the desperate need for a “relationship”; find men whose company you enjoy; sleep with the ones who can make you laugh; be friends with the ones who don’t. All of these ARE relationships. And there’s love in ALL of those kinds of relationships. Just not the fairy-tale kind.

    This doesn’t mean giving up the dream of finding “the one” to spend the rest of your life with (I haven’t) — it just means that you need to enjoy the journey on the way to your destination. And you’ll find happiness–and sometimes heartbreak–along the way. You’ll survive the heartbreaks far easier than surviving a life without happiness. Just choose wisely, even for “rebounds”.

    “Love doesn’t make the world go around; love makes the ride worthwhile” – Franklin P. Jones

    1. 10.1

      Karmic, glad it’s working out for you. Not my thing. Doesn’t make either of us right or wrong, it’s a preference issue.

    2. 10.2

      First off Evan, I would like to say that I did read and acknowledge your dislike of my many questions in the comments section and for that I apologize (I’m a huge fan of yours and I look forward to hiring you one day after I get back to the states and graduate med school), it only took me so long to respond because I’ve been extremely busy with school.

      Dear Karmic, I just can’t help being a HUGE fan of yours and envying your *old man* boyfriend (^_^). THANK YOU for setting it straight, people love to jump on the age band wagon, but it’s mostly always just boils down to life experiences, age really is just a number… as long as they are a legal adult.

      I am now studying abroad over here in Europe and one of the strangest things that continually happen to me is having older women (I’m younger than your boyfriend, and the women ages range from the early 30’s to the late 50’s) hit on me or just bluntly and unapologetically ask me out. I don’t think this would happen back in the states.

      Since its happened to me so much I’ve learned a few things about older women wanting to date arm candy… I mean younger guys (^_^). Most older women like to date younger guys because it makes them feel attractive and desired, and also for the sex. Younger guys have more stamina (guys don’t flame me for that, I’m only repeating what I’ve been repeatedly told), plus as many female commenters here have noted in other post, no one wants to be with someone who they have to take care of because of bad health or someone who is boring and unable to get out much. But the biggest motivator that I’ve noticed personally, with the desire for older women trying to date me or other younger guys is the power of control that the age advantage gives them (Karmic you seem too cool to do this). I don’t mean control like a robot, I mean control more along the lines of trying to mold the younger person. Most men and women by the time they reach their mid 30’s have a ridiculous prejudice about attractive people of the opposite sex, sure women want the hot, successful guy but most think because of his looks he’s probably a player and he will cheat on them, but a younger guy she can get addicted to her mentally by doing things in and out of the bed room that a younger inexperienced girl wouldn’t do because of lack of knowledge, lack of confidence or both; so in a sense it’s a fear based control. Also Most older women unlike men, won’t date a guy who looks so young that she feels like she is with a child when they are out in public, but she still may consent to a friends with benefits deal she feels that he is emotionally mature enough. Of course what I’ve repeatedly seen is that he isn’t, so he gets emotionally attached, chases her romantically with the passion and power to move a mountain, until she hesitantly agrees at first, then she eventfully falls in love only to have him eventually leaving her heartbroken because he doesn’t have the maturity to understand that you always will find someone who is sexier, funnier, more intelligent than the one who you are with. The temptation, his lack of self control, his inexperience and immaturity toward monotony in a relationship, causes him to succumb to chasing after the seemingly “better” and most times younger woman

      I hate to admit it but I completely agree with your statement about getting to serious or emotionally attached to someone with such a large gap in life experiences, because a younger person will be passionately in love with you and make you feel like you are the most intelligent, beautiful and sexy person in the world to them and honestly they will mean it… in that moment! That’s the trap that I’ve seen most older men and women fall into when dating someone in the 18-25 age range, they will convince themselves it could work because the younger person saying those things seem like they really means them… and we DO! But their hearts are fickle, what is true for us to day, will probably change tomorrow. We do love you with all our heart and we honestly mean it… in that moment.

      As for the original letter writers boyfriend, most guys I know love the sexual myths about older women, their confidence and boldness, and looks are also a very important factor. When we younger guys fantasy about being with a older women, it’s not the ones who look like grandmothers, or who are out of shape, it’s the women who take care of themselves and look sexy. I think the original letter writer is so disgusted because when she thinks 40, she visualizes the grandmother type not the Halle Berry, Salma Hayek, or Jennifer Aniston type of 40 year old women..

      Everything I’ve said is a HUGE generalization based off what I have personally seen, heard or read about, I’m not saying all men or woman are like this.

      1. 10.2.1
        Karmic Equation

        Aww. Thanks for the kind words Gabri’el. If you’re ever in the Boston area when you’re back in the States, let me know. We can shoot the sh*t as well as some pool over drinks and apps and discuss EMK’s blog 🙂 It will be a blast!
        “I think the original letter writer is so disgusted because when she thinks 40, she visualizes the grandmother type not the Halle Berry, Salma Hayek, or Jennifer Aniston type of 40 year old women..”

        Exactly. She’d feel insecure or get mad if she found out the 40 yo was like the gals you mentioned.

  11. 11

    She’s only 19. Of course it’s creepy to her. I remember being in high school thinking college students where so much older and mature. Thinking late 20’s was old. 40-something would be ancient! She’s probably putting herself in his shoes. She can’t image at 21 sleeping with a man that is 40-something with children older than her without it being creepy and a mistake.(A point of view many on here would agree with btw…)

  12. 12
    Karmic Equation

    My last bf dated a 62-yo when he was in his mid 20s. I met him when I was 45 and he 33. He preferred dating older women.

    “So how old was the oldest woman you ever dated?”

    “62. She was a model when she was young. When I was at her place once she showed me her modeling portfolio.”

    “62?? Wow. And how old were you?”

    “About 26.”

    “So how many dates did it take you to get in her pants?”


    “And how long did you date her?”

    “Three dates.”

    [I rolled eyes and changed the subject.]

    1. 12.1

      (LOL) Beautifully done, I say . . .

  13. 13

    I am almost 47 and my sweet, loving, faithful boyfriend is 24 1/2. Yes, I am 22.5 years older than him. I don’t know if I was ever more in love than I am now. He dotes on me, cherishes me, and makes me feel so loved and nurtured. At first it felt kinda weird and we were slow to really go for it. But the heart wants what the heart wants. I can’t imagine my life without him. He feels the same way. Our bedroom life is loving, sensitive, intimate, and sexy. But because we love each other so fricking much, we don’t think about how weird it may be to others. Strangers have suggested that he’s my son, but we laugh about it and play along. Oh, and his mother is my age. That took some getting used to. But age is just a number. You fall for who you fall for. I never had kids because of my career, and he was a teen father. So that part works out great, as well. If it’s meant to be, it will be. And I have no doubt that this young lady loves certain qualities about her boyfriend that this cougar taught him. She should let go of her insecurities and embrace this dynamic young man who she can call her own. If she continues to question him, she will lose him. Just like our world is breaking free from discrimination toward gay marriage, our world is realizing that it’s no big deal for persons of far different ages to have relationships. Hell, you see it all the time in the movies! And one last thing… Being in your 40’s isn’t old at all. It happens to all of us, and quite fast at that.

    1. 13.1

      That is so beautiful. I’m so happy for both of you 🙂

    2. 13.2

      Great post, congratulations to you for forward thinking. You are both grown up adults. And yes 40 something is not old. You could still have kids too. My grandmother had her last child at 47yrs old. I read an article about a 50 yr old woman who had her first marriage at 50yrs then 3 kids, one after the other, natural births at 50,51, and 52yrs old . Googke it , it was a British woman

  14. 14

    You should drop it. Stop trying to make him feel guilty.
    And I expect that there are those who think YOUR age difference is beyond the pale!
    “Is it creepy that my ex dated a virgin five years younger than him?”

    1. 14.1

      Great reply Marymary ! In fact, I do think there was a letter on this blog and a lot of people were up in arms about a 20 something year old guy with a “teenager” of 19.

      People have to stop dwelling in the past. ESPECIALLY the past of their significant other !

  15. 15

    It is *gross*. I can understand where the writer is coming from. I am in my mid 30s and am surrounded by cute 20 year old boys because I have gone back to university but on some level, what the heck would I want with a 20 year except pure sex? I want to get married and have kids so this would be a waste of my time. However if I was married or divorced with kids, than yes I’d probably be less discerning.

    It is “gross” in a way when people live unconsciously, which is what her boyfriend and this woman did but people have the right to indulge is pure, meaningless sex. It’s more understandable when it’s someone young but when it’s someone old, it makes you wonder where they are in life and on some level seems desperate.

    but since he did this before you were together, who cares anyways? You guys will probably not end up married and you will most likely be one of the many women he sleeps with. he seems a bit of a ‘slut’ if you ask me and I wouldn’t put much stock into him

    1. 15.1


      I know someone who is 19 just got engaged to her first boyfriend, also 19. They have been together for over four years. Both at (different) universities now. You might think that weird. Those of us who know them found it entirely expected.

      She might think it weird that someone in her 30s is still single, especially if they want to start a family.

      As much as you judge other people, they could be judging YOU.

      1. 15.1.1

        I could care less if people judge me. we all judge people to some degree. I am just more vocal about it than others but we all do it. no one here is a saint. it’s human behaviour so I don’t let it drag me down. I’m also not afraid to be seen as weird anyways.

        And if you are a regular EMK reader, he does cite the stats on those married under 25. The odds are not in their favour and at this point, it’s merely a ‘wait and see attitude’. Not saying it’s not possible, just the numbers are not in their favour.

        1. Me

          I’m always saddened by doomsday predictions for young married couples. I married at 20, had all my kids very early while studying, have a successful career and a loving marriage of 23 years so far. I’m only writing this in the hope that some young person contemplating marriage early because they connect to the person is not turned off by a ‘wait and see’ attitude.

          We had people around us who  believed in us  and supported our union which gave us confidence. Encouragement and support and any age for marriage is needed by couples as their are not much better stats on length of marriage for older couples or remarrying couples either.

    2. 15.2
      Karl S

      Judgmental much? I’m currently enjoying a casual thing with a lady friend who is 10 years my senior. We get along really well, and it’s more than just purely physical or living “unconsciously” as you put it. I’d say it’s quite aware. Aware enough to think “Hey, we’re both adults and we can enjoy this connection for whatever that’s worth.”

  16. 16
    Robert J.

    I don’t mean to be condescending at all… And, I apologize in advance if you proceed to process the information with your E: (Emotional Drive) in substitution for your L: (Logical) one. But, by nature, we have not yet evolved back into the marriage/ traditional roles, because as we all know it, society is an ever-changing fabric.

    No one likes to be grouped either—even though many of them choose to belong to groups. Hypocrisy any? Reminds me of the racial slurs different races are allowed to say.. ha… Humans will always be hypocrites. It’s built into the human condition—mainly for survival conditions. That is changing however over time, because as tribes join together and groups emigrate into communities and governments are established, societal decisions from parenting to monetary concerns are also founded; sometimes broadened and or narrowed down into specific categories. Like the iron clad of the women’s rights movement or the establishment of affirmative action to go beyond it’s means—without massive political takeover—tends to bring new ideas to the table. Eventually the old systems will fade away and more than likely, forever to be forgotten, except for in the attic of a 214 year old library…..In this case, I’m referring to the “Federalist Papers” now located on the 92nd shelf of the side stair balcony of the Library of Congress.

    I’m tired of typing…. basically what I’m saying is that men, by nature, are wired much differently. When a man gets married in today’s era, he is virtually ignoring his own natural instinct to seed as many women as possible. I know you will try to denounce this, but this is only because society has deemed it unacceptable to cheat… And I’m not saying it isn’t wrong… I believe it is. On the other hand, I can’t throw out the fact that at one time, civilizations rid this practice and created a system of marriage… Pagans did this actually… And this was long established before any religion such as the RCC was created.

    Society also tends to have sympathy for the weaker (by nature) sex: females. Rather than holding them accountable for their actions, they’re coddled, which is why more double-standards and confusion arise. All of this because society deems it necessary to enforce political correctness as to hurt no one’s feelings, but a man’s… And if he is of an ethnicity other than any anglo (within western countries), he will certainly be given a pass.

  17. 17

    not really…attraction is attraction.
    some      20 years olds are not that bright or interesting.. maybe she had charisma.
    I think that he would have sex with a 41 year old but not date a 41 year  not nice..
      you should be more concerned with that?
    Do you think you are better than her simply because you are younger??? you too will be 41 one day and will you not  deserve to be seen as sexually attractive?

    so  BASICALLY..get it out of your head and stop this worry about something  not important…                

  18. 18
    Karl S

    I recently came across a study that talked about how the age at which your parents gave birth to you can play a role in the kinds of faces (young or old) you’re attracted to. Given the classic adage that you end up falling for the person that reminds of your parent of the opposite gender, maybe it’s not complete bs.

    1. 18.1

      My parents had me at 23. I am pretty much always attracted to men in their mid-thirties to mid-forties.

    2. 18.2

      Wow Karl Thank you!   While I am much older than my boyfriend, his mom is still old enough to be my mom because she had him after 40. Plus his Dad is younger than his mom.   Yes, explains a lot.   Nevertheless, I have not lost my logic about our affair.   We seem meant to be together now, and we are both learning a lot.   However, I have not forgotten he will want to marry a woman to bear his child later on.   

  19. 19

    It is natural that a man of age 20 should marry a woman of age 50 it is physiological and good.

  20. 20

    EMK nailed it and so did RustyLH.   Its about the individual.   When you have met that person that holds your attention and makes your heart beat faster,   it doesn’t matter how old he/she is.   Its about the individual.

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