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. 241

    I happen to be 44 and my other half is 26 ♥ I question all the time the age difference BUT I also know that this is so much more than some have said. We spent countless hours together – every day – for 6 weeks with no sexual contact other than a little hand holding and some kissing. When we finally crossed that bridge, it was when we were both ready.
    I’ve spent time with his mom and step dad (they are totally ok with the relationship and adore me as I do them) We’ve been around each others family and friends – most seems to be ok with our decisions.
    I made sure from the beginning to lay all the cards on the table though. He knows I can’t give him children and all I have to offer is ME!! He asked to move in and share this life with me. He has recently started to talk about marriage ♥
    My only issue is when we’re out (like today) and we run into his friends that I haven’t met and they say things like “its good to see you hanging out with your mom” That stings a little bit to be honest! But his response is that he doesn’t care what people say or think because he loves me and he loves his life more than he ever has before!

  2. 242
    Moninca Martinez

    Oh my God, i can’t believe i found this blog, I am 44 and he is 25, but we have the most fun ever together, we are the best friends, we tell each other everything, we do not have sex every time, but we spend a LOT of time together, The issue is that he has clear that we are just “friends with benefits” 🙁 i tried to think in the same ways but i have feelings for him, i told him that, but he responded me that he is looking for a serious relationship, it broke my heart, but since the beginning he told me that. He doesn’t want to have kids so that is not the issue, he told me last week, that he has incredible fun times with me, that he cares a lot about me and he enjoys spending time with me, we have been doing this for over a year. I told him i do not want to see him any more he did not like that, he says if finds a girlfriend he will still be my best friend (not more benefits) i have never been just friend with someone i had sex before so it won’t be easy for me. He said if i were 35 we were probably being engaged already ouch!:( last night he proposed me to enjoy what we have right now, i know that this is going to hurt me, i know what to do but it is so difficult to let him go 🙁 thank you for reading, i know i am stupid for still being with him, i wish i would have the strength to leave him.

  3. 243

    I’m 45. I went back to school. Younger men hit on me. I don’t know how old they are, but they are much younger than me. I am overweight. There are young, pretty girls in the class, probably wouldn’t give these guys the time of day, or as one person said, it would be too much work/commitment for the guys. It makes me self-conscious and kind of stresses me out (hence being here trying to figure out what is going on). There is no way to make them stop. I just have to ignore it and put up with it. At first I was a little flattered (fooled), but I want to thank all those people who are telling the reality of the situation, that in 99.99% (100%?) of the cases, the guys are just looking for easy sex, or just playing around for who knows why (I would hate to waste my time that way). It’s not flattering at all. It’s embarrassing and burdensome. But now that I know what the deal is, this will be much easier to put to rest. Thank you to those people who were kind enough to brave the flak to give me a reality check, and a heads up.

  4. 244

    Okay so, put this into perspective. I am 21 years old, my boyfriend of 6 years is 22. I just recently found out he was with an older woman she is 42 recently and he has betrayed me (completely his fault for breaking my trust and disrespecting the relationship.) This 42 year old WOMAN is telling him that he needs to hide her from me and is sneaking around like its fun for her. Now if all of you ladies are of that age dating younger men, how would you feel if your child was upset because somebody that is YOUR age slept with their partner and broke them. I think you’d be pretty upset and want to protect your child from SOMEBODY WHO SHOULD KNOW BETTER. How does it feel to have no regard for the fact that there are plenty of 22 year olds that with people that are in their age group and you are coming into it with your selfish desires due to your failed attempts at people your OWN age. You ” ADULTS” are supposed to be the voice of reason at these confusing times in our lifes. How could you subject anybody to that immature behavior after living so many years longer than I. I trusted that the older generation wasn’t a bunch of selfish jerks but now I am not so sure. All of the women I looked up to now I do not trust. Looking at this makes me feel queezy because you all know FOR A FACT that ANYBODY whom is 20 years of age and or under 30 has allot to learn and a allot of life they have yet to to live. Leave the “cabana boys” to the CABANA GIRLS. Even reading this I am sure you know that this is coming from a place of pain but why must you be the ones to cause it ? Sincerely, a 21 year old girl who trusted that you knew better.

  5. 245

    I’m 42 years old, divorced a few years ago and single still. Putting my life back together. I have one son from that marriage, he was 18 at the time, and he walked away from his parents divorcing quite angry. He lost a lot, and hates his father. Now my son is dating at 38 year women, he’s 21 years old himself. In a weeks time they have practically moved in together. I find it disgusting. I don’t know what you women see in dating a BABY. Okay maybe when they are 26-27 when they’ve had time to grow up some. But 19-22? They are barely even adults.

    For those of you with kids, think about how you’d feel if your daughter or son started dating someone 15-20 years older. Would you really be okay with it? Would you question that persons motives?

    I am struggling with this big time. My son isn’t the type to just want sex, he wants a relationship. He has also always wanted kids. She may not be able to provide him that, but oh she does have a 10 year old son that he can play step-Daddy too. Only they are closer in age then him and the girlfriend. I’m sorry but for me it feels like a “to catch a predator” episode. Stop messing with these young guys just to boost your fragile ego, or fix your midlife crisis. I’d say the same to the men who feel the need to have a perky 20 year old girlfriend. I’d rather stay single the rest of my life then date someone who was watching Blue Clue’s the same time as my own son was! Puke.

    But now I’m supposed to meet her, sit across a table from a woman who is MY age involved with my son. I seriously don’t even know if I can do it.

    1. 245.1

      Yes.I know it’s hard on you. But the fact is it will help your son grow.
      When my son had a fling with an older woman .I felt like maybe i was not a good mom that he had to take another one.
      I was like”that’s my boy,not yours.
      But i came to know my son’s girlfriend herself had a son just 5 years younger than my son.She wasn’t faxed by it and her family was cool.
      I wondered why a young man would date an old woman?
      My son told me young men love older woman just like young girls often love older guys.
      My son encouraged me to date younger guys.
      I was hesitant but i allowed it to happen.
      I am now dating a hoy 25 year old ,3 years younger than my son.
      He is rocking my world now….

  6. 246

    I’d get with older women when I was in my 20’s all the time. They thought it was because the sex was easier for me to get but the truth is I really liked when they brought me milk and cookies or a nice sandwich afterwards because that made me feel so special. Just laying there in bed, eating all those cookies…. And she’d be all like “Is that GOOD?” and I’d be all like “MMmmM HMMMMM! So good!” Like, sex, milk AND cookies from the SAME person on the SAME night!! I know, right! Seen in public? Pushaw. Who needs to be in public when you get sex and cookies and little BLT sandwiches with the toothpick in them right there in bed. And then they’d wash you up afterwards like you’re a freaking newborn or something! Head to toe. Q-Tip your ears and everything. Hey, where’s my clothes at? THEY’RE IN THE DRYER! Can you BELIEVE IT?! I KNOW!! I didn’t even see her go to the laundry room! Wow. It was so awesome. Now, my friends kept saying “You gotta stay the hell away from our moms dude!” but I didn’t care. I knew I had a good thing going.

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