What Do Guys In Their 20’s Want With Women In Their 40’s?


I am in my mid-forties and I have been online dating off and on for about 2 ½ years and dating in general for 4 years. I am a year and a half out of a relationship and in that time, I have found only one guy I was interested in but he did the vanishing act. I have probably more dates than the average woman and I just can’t seem to find a guy I want to date. I am often told I am beautiful and I look about 10 years younger than I my age. I get contacted by a fair number of guys in their 20’s and most I don’t respond to because I just feel it won’t go anywhere. Recently, however, I was contacted by a guy in his mid-twenties and I was impressed by his profile…he’s mature, intelligent, articulate and attractive. I started up a correspondence with him. I was curious. But I still feel that maybe it’s a mistake…what do I really have in common with this guy? After all, I am twenty years older than he is. 

In your opinion, what do guys in their twenties really expect and/or want when contacting an older woman?  The youngest guy I have ever been out with is 33. 

Thanks for your insight. I really enjoy reading your blog and I feel that of many so-called dating experts that you are right on!


Thanks, Coug–, uh Carla. As a so-called dating expert, I really appreciate the kind words!

Which is why I’m sure you’re going to be completely receptive to this:

You’re wasting your time with this kid.

Okay, that’s not fair. Let me use more words to say it:

If you’re looking for a long-term relationship, you’re most likely wasting your time with this kid. However, if you’re looking for good, clean (and not-so-clean) fun with a young stallion, you can have an amazing time. In fact, I would encourage you to do so. And take lots of pictures.

If you’re looking for a long-term relationship, you’re most likely wasting your time with this kid. However, if you’re looking for good, clean (and not-so-clean) fun with a young stallion, you can have an amazing time.

See, I’m not here to set the rules for society. I’m here to observe society and report back to you how things USUALLY work out. And for every Demi and Ashton (Celebrities, They’re Just Like Us!), there are thousands of other instances of cross-generational relationships that die a quick, painless death. Why? Because he was born in the 80’s, right about the time that you were losing your virginity in college. Because he’s been in the workforce for oh, about four years. Because he may be a great communicator, mature for his age, and relationship minded, but he’s also, y’know, a BABY.

You know how I know this? Because I’M that guy. I’ve ALWAYS loved older women. I was with a 35 year old woman when I was 20. I used to flirt with my mom’s friends. And when all my friends would make fun of me and say, “Why would you date an older woman when you could date a younger woman?”, I’d say, “Why would you date a younger woman when you can date an older woman?”. … As far as I’m concerned, every woman is better at 28 than at 23, better at 33 than at 28, and so on. Now, there is a flaw in this system – the biological clock — which is much worse at 38 than at 23. This is a valid concern to men looking to have families, so let’s not overlook it. But still, I’m a big proponent of life experience and wisdom. Older women are AWESOME in this guy’s book.

So even if this young man’s interest in you is completely pure, even if he wants to have a real relationship with you, you guys are most likely doomed. If he wants to have kids. Or go clubbing at night. Or switch careers a few more times. Or do normal things like twentysomethings do. You’re at the home buying, 401K saving, family planning phase of life — for MOST 46-year-olds. Hey, if you still have the juice to hang with kids, go crazy.

There’s a very good reason that you don’t see many 25 year old men with 45 year old women.

It just seems far more likely that a) he’s bragging to his friends that he might get to sleep with a woman 20 years older than himself, or b) you guys really might be compatible if only he were significantly older or you were significantly younger. But he’s not. And you’re not. Put another way, there’s a very good reason that you don’t see many 25 year old men with 45 year old women.

A caveat which I must acknowledge: if neither of you desires children, then you have a far better chance. But presuming he does, if I were you, Carla, I’d probably have some fun. Go in with your eyes open and appreciate the experience for what it is — a dalliance with the youthful exuberance of your past. Enjoy it while it lasts.


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  1. 41
    Karl R

    Caley, (#39)
    Without knowing all the details, I would recommend that you just let it go.

    Things to consider:
    1) If he’s interested, he may be trying to conceal that interest. That’s what I did (at that age & younger) when I had a crush on women who were inappropriate to date. Why tempt him when he’s working so hard to act appropriately?

    2) At some point in his teenage years, your son will have a crush on someone much older than him. Try explaining to him why it’s wrong for him to date someone 14+ years older, when it’s okay for you.

    3) Most 20 year olds haven’t taken responsibility for their lives. They’re in college, or living at home, or receive substantial support from home. If he’s been supporting himself for a few years (without assistance), that might change the story.

    4) Even if he is responsible enough to support himself, he’s probably not mature enough to be a father to your son. That rules him out for anything more serious than a fling.

    5) Unless the kid’s mother is extremely open-minded, you would lose your friendship with her if you got involved with her son.

    6) There’s nothing wrong with thinking this kid is drop-dead gorgeous and wishing you were closer in age … provided you don’t act on those thoughts.

    7) Avoid temptation. Make sure you don’t spend time alone with this kid. It will be a lot easier to act appropriately if you have a chaperone (even if it’s the 5 or 7 year old).

  2. 42
    For Selena

    “Selena Feb 28th 2008 at 01:29 pm 6

    I believe men have a biological clock too. Men in their 20’s & 30’s may say they don’t want kids (or may mistakenly believe they are sterile) but may start to feel otherwise as they approach 40. If you are a woman in her 40’s-60’s you are biologically done with that, and may well not want to start the childrearing process through adoption either. Something to think about when contemplating dating someone much younger with LTR in mind. ”

    Learn something about biology, toots……..women in their 40’s have babies.
    You give credit to men but not to women. How cloying and man-pleasing. I feel rather sorry for ignorant people pretending they are knowledgable. Hint hint, honey.

  3. 43

    I am so happy I found this post. I am also 44 and am dating a 25 year old guy. He thinks I am in my 30’s because I look like I am in my early thirties. I never asked him hold old he was, but when he was in the shower, I saw his driver’s license on the floor next to his pants. He makes me laugh, isn’t too clingy and we have amazing sex. We have been seeing each other for a month and a half. I have met some of his friends and they are all really nice and respectful, but I have to admit, sometimes it feels strange. I totally didn’t think that I would fall for him, but I am developing big time feelings for him and find that I get jealous of the prospect of him dating someone else. We haven’t even had that “conversation” about exclusivity. I treat him very well, cook for him, etc and he treats me well. He is so easy to talk to. I have tried to date guys my age and it is a nightmare. I am always approached by guys in their 20’s. I have had a fling or two in the past but it never went anywhere from there and I was fine with it. However, this guy is different. After we met, we spent 11 straight days and nights together and it was amazing. I just don’t know what to do now that I know I am falling for him. I can feel him pulling back. I know he is getting pressure from his family and I know my family and friends kind of think it is strange. At first I just wanted to have some fun, now what?

  4. 44
    S. Williams

    Hi Marie,

    Why do people put so much stock in what others think?

    I couldn’t care less what other people think about my personal life.

    It is like having an invisible leash, you can only go as far as they (the people holding the leash) will let you.

    You can’t pick your family, but you sure can ignore them, and far as your friends go…if they don’t support you, you might need some new friends.

    Life is a journey to explore, not live by some ever shifting sets of rules created by people afraid to really live their lives.

    I say you talk to him about your relationship, and if it’s only what other people think that’s in your way screw’em…it’s your life, right?

    Good Luck! I hope it all works out for the best.

  5. 45
    J Marie


    There was a young guy, 20 something in a class I met. He was half Brazilian, such a cutie. I never had kids or alot of younger guys in my family so he was something intriquing to me. I was in my early 40’s at the time. He was very warm and affectionate, always huggy and wanting to talk to me. We talked about sports cars, and sports during breaks ect. I seriously think he wanted to date me. However, I couldn’t so, offered “life mentoring” instead.
    I was almost embarrassed by his boldness and flattered at the same time. He flirted with me. I found out he liked certain parts of my female atributes,lol. Anyway, to make a long story short, he didn’t want friends with me, just either a lay or a relationship with me. Hence the age. Remember how you where in high school? He still brags about me, but not so much. It’s dying down. So he wanted, a lay, or a relationship, and bragging rights to his friends. I realize about the bragging rights, now because he shared some emails of mine to some mutual classmates we knew. Found that out later. I think he just got mad that he didn’t get any. He wanted to show me off to his family and friends. I suspect a little wanting to thank me for helping him out in class there to for his reason to take me out, but I never wanted to officially date him. Just hang while in class. Just be careful who you pick at that age. I don’t have bad vibes towards him, just not what I expected.

    Good luck and do some investigating:)

  6. 46

    my husband and i have an 11 yr difference and the ONLY one that has a problem with it is ME!! yes, i heard all of the negative comments, especially from women that were miserable with their bodies, marriages, etc, and had nothing else to do but down our relationship…

    have had multipe younger guys hit on me all the time, not interested in kids at all, like my independence, and certainly know that there is ONLY ONE LIFE TO LIVE SO FRIGGIN ENJOY IT!!!.

    live for yourself older women and if you are lucky enough to attract an younger man “””” GOOD””” but keep it real and make sure you are mid 40s’ try someone in their mid 30’s…,



  7. 47


    I have the opposite problem you do. Men my age (30) don’t pay attention to me (I’m not counting catcalls), and the ones who do are old enough to be my father. And there is absolutely no way I’m ever dating anyone who’s more than five or six years older than me.

    I do get a lot of 18-year-olds who flirt with me, but that doesn’t count, since I can’t do anything about it.

    I know this is going to sound bad- but I am going SOLELY on what I’ve observed around me and with friends- I really think I would have had no problems with my love life if I’d been an Asian woman.

  8. 48


    Why do you think it would be easier to be an Asian (presumably East Asian rather than South Asian) woman rather than, say, a Caucasian one?

  9. 49


    lol- probably because all my Caucasian girlfriends are single like me and the Asian ones aren’t. Please excuse my post previous post- it was induced by sleep-deprivation and an overall bad mood. (But my observation still stands)

  10. 50
    Karl R

    camille said:
    “my husband and i have an 11 yr difference”
    “but keep it real and make sure you are mid 40’s try someone in their mid 30’s”

    There’s a world of difference between a 10 year age gap and a 20 year age gap. I’m in my late 30’s. Women 10 years younger than me are out of school and have had time to get steady employment. Women 20 years younger than me are in college. Women 10 years older than me make up a substantial portion of my yoga and dance classes. Women 20 years older than me are candidates for early retirement.

    It’s going to be a rare couple who can bridge a 20 year age gap as equals.

    Sayanta said: (#47)
    “there is absolutely no way I’m ever dating anyone who’s more than five or six years older than me.”

    Why not? Regardless of the criteria you’re using to choose a partner, I can almost guarantee that you can find someone with a 10 year age difference who still meets them. The women that I have dated who were +/- 10 years certainly weren’t average, and that allowed them to compare favorably with the women my age.

    The woman who was 11 years younger than me had the emotional and economic stability that I would expect from a date who was my age. The woman who is 9 years older than me has a fitness and energy level that rivals mine (substantially more than I expect of a date of any age).

    Sayanta said: (#47)
    “I really think I would have had no problems with my love life if I’d been an Asian woman.”

    This made me laugh. Where I go dancing, it’s almost cliche’ how many older men (usually the skeezier older men) practically line up to dance with the younger Asian women.

  11. 51


    Long story short- I’ve never been in a serious-serious relationship, and I don’t want my first one to be with someone too much older than me.

  12. 52

    I don’t think women go out of their way to meet younger men; they often try to to avoid such relationships. With that said, there is nothing wrong with having a serious relationship with the opposite gender that happens to be much younger or older than you. No need for games or hesitation. It’s part of the life experience even if your heart gets broken. As an adult, being able to trust another individual is an indication of strength; there’s too many bitter adults in this world. We need to nurture that innocent part of us that can keep on trusting others. Loving others and not expecting anything in return is the greatest gift that one can offer another. Older women may be attracted to younger men because these younger men love with sincerity, but down the road, society may influence their way of thinking which leads to confusion and doubt; eventually, the relationship may fail. I personally feel that many of the relationships mentioned above are very sweet and sincere. All of you should be thankful to have experienced such emotions and cherish them, because if you look carefully within, you may find that little kindled fire still burning inside which may be the source of your youthful natural appearance. Have you notice women who date younger men look extremely young and healthy for their age?

  13. 53

    I am 51 but most people think I’m at least 10 years younger. I like the energy of younger men but I prefer to stay within 5 years give or take. It’s all about having things in common.

    I was in a serious relationship with a man 11 years younger about 5 years ago. MISTAKE. I didn’t have a problem with the age thing but I did start to have issues with his lack of life experience simply because he had not had a chance to live through certains yet.

    About a month ago, I met a very handsome young man who I though was in his 30’s. He’s written a couple of books and we discussed those. I gave him my phone number. When he called, I asked him how old he was before we got too far into a conversation. He is 24!!!!!!! OMG!!!!!!!!!!!!!!! He saw nothing wrong with the age difference. I have 7 year old daughter. I told him that he closer to her age than mine. I have nieces and nephews older then him. I feel like his mother. He just kept saying that I was so cute and seemed like so much fun. Yes all that is true (LOL) but at my age, life is about so much more than being cute and having fun.

    He keeps calling. I won’t take his calls. He’s too sexy and It’s been a loooooooooooong time since I’ve been with anyone. I don’t want to go out like that. ROFLMAO

    1. 53.1

      Mura, Why not let your heart take charge???   Even if it is just a short fling. It will do you wonders. Something similar happened to me and after a time, I went on several dates with him. He made me feel like I was 20 years old. I for one don’t see any problem for you two to date and it would do you BOTH a lot of good!!!!   Please let nature take its course in this matter, Don’t cheat yourself, he just might be the love of your life !!   It has happened to other women countless times.

  14. 54

    I had a 26-year-old beg me to go out. I believe I was 36 at the time. I might have been receptive had he not started whining like one of my kids when I hesitate. Real turn off.

  15. 55

    Well, it turns out things didn’t work out with the young guy. In March I went to Chicago for a week and when I got back, things seemed different from when I left. I was worried that that was going to happen as I knew his sister was against the whole thing and she has a big influence on him as he lives with her and her boyfriend. I knew that a neighbor his age had a big crush on him, so I am guessing that he got together with her when I was gone. It wasn’t so bad that that happend, it was just how he dealt with the situation. Less then a week after I got back, he avoided me and then he basically just dropped off the face of the earth with no explaination whatsoever. I mean I can see no explaination if it has only been a few days, a few weeks, but we had been seeing each other for a couple of months and I know he had feelings for me. I flat out asked him if he was seeing some one else, and seriously that would have been okay, I just wanted the truth and some closure, but never got it from him. Oh well, guess it must be a maturity thing. If it was me, I would have at least talked to him and told him what was up.

    1. 55.1

      Lack of maturity…even older men do the same so it’s not the age thing; some men lack maturity and will never grow up. It is also lack of respect for your feelings and selfishness. Not wishing him anything bad but the Universal law is Karma and sure he’s got his coming.

  16. 56

    I’m sorry to hear of the break up. Some people find it very difficult to tell the other person the reason for the break up because they still care for that other person. Hopefully, it’s not some stupid misunderstand. When we really love someone, we try to respect their wishes even if it hurts us. I think it’s beautiful how people fall in love with one another.

  17. 57

    does anyone see anything wrong with a 31 year old woman (me) dating a 20 year old man?….. the 20 year old looks likes he is under 20 but his drivers license says he is 20….a relative told me that when we are together in public that people probably think i am his mother… but i know i do not look that old to have a kid that big… people say i look about 25… any response would be appreciated….

  18. 58

    Monica #57

    Well, when you go to a restaurant you won’t be able to share a bottle of wine with him. lol.

    Does it matter if anyone else sees “something wrong” with it? Isn’t it really about how comfortable YOU are with the relationship?

  19. 59

    Wow, had a 24-year-old hit on me and now my brain is short-circuting from all the diametrically opposed advice. Evan, I would be interested to know WHY you recommend a woman give serious consideration to entering such an arrangement (because let’s face it, it’s more often an arragement rather than an actual relationship).

    1. 59.1

      It would be about sex and would likely not last. That could be a good thing! If it is for you, mazeltov!

  20. 60

    I view it as a waste of time, but hey, if it’s for someone else, far be it from me to judge.

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