“No Girl Who Is 23-Years-Old Should Be Sleeping With A 23-Year-Old!”

Jennifer: Okay! But I think that works for me because my interests are very dull, and I just don’t have the party-all-night streak that many men in their 20′s seem to.

Ashley: Not to flatter you too much, but I think after 22/23, smart people should feel free to date much older. Not just for sex reasons.


Ashley: …Turner Classic Movies?


Ashley: That’s prescient of them.

"Attention Feminists!"

Jennifer: So, this is why. This is why I can only date older men. I agree with you, incidentally. I kind of feel you should date based upon your common interests?

Ashley: That’s certainly part of it.  I’m reminded of being at a bar once and this guy coming up to talk to me and a friend of mine. She and I were talking about Plato or something people who recently graduated talked about and he followed along for a few minutes and then sighed to show his exasperation and declared, “Talking about stuff like this… just makes me want to fuck.” Right around then was when I decided I should probably skew older, romantically.

Jennifer: Yes. At the same time, I hear some of the people I’ve dated – 90% of whom have been terrific – describe what they were like in their 20′s and I think “oh, wow, you sound like you were a nightmare person. I am so glad I did not meet you then.”

Ashley: I mean, we were insufferable in our late teens/early 20s, too.

Jennifer: True. Maybe no one should date anyone in their 20′s, or be in their 20′s themselves. Maybe as soon as you graduate from college you should be strapped into a wheelchair, handed a catheter and some Frank Sinatra LPs and told to behave accordingly.

Ashley: I like the idea of no one being in their 20s. I think we should just put muzzles on 17 year olds, take their internet away and send them off to monasteries to read On The Nature of Things over and over again in Latin until they come out with some healthy shame and dignity. And self-loathing, obviously.  That being said, I’m kind of leery of the idea that “middle aged bankers” are the Cerberus at the gates to “good, interesting sex.”

Bankers or megamoguls.

Jennifer: You don’t think they teach you to do it like they do in Berlin? In my experience they’re mostly tired because they have to be up in three hours. So, I guess if the way they do it in Berlin is “really, really sleep-deprived” that’s something.

Ashley: I kind of agree with the sentiment that 23-year-olds should probably be out broadening their horizons instead of having sloppy 5-minute missionary after too many Tequila Sunrises. Wait, what do 23-year-olds drink? Vodka-cranberry? Vodka cran.

Jennifer: We were never 23, were we?

Ashley: You know, I think some people are 23 at 20. And 20 at 17. And so forth.

Jennifer: Right. I’m 112. My tenuous grip on sanity is loosening.

Ashley: Every day.

Share This Post:
    • Lastango

      Is this going to get any traction with younger women? Here’s a quote:


      When I was in my 20s, I wouldn’t give a man in his 30s (let alone older) a second glance. It really disgusted me and my friends when they approached us. Now, in my early 30s, I still have no desire to be with a man in his 40s. And I haven’t met a single girl in my entire life that wanted to be with a much older man. NOT ONE! We want men our own age, plus or minus 5 years.


      BTW, that bit about “Should we all just be dating older men who love capitalism” is rich. There are no actual capitalists at Morgan Stanley. There are only “crony captialists”, joined at the hip to their partners-in-crime in Washington so they can use the machinery of the fed, HUD, FANNIE, FREDDIE, and other federal government fraud factories to loot the rest of us.

    • MR

      First, that guy looks 60. I look 45. :) Yeah, as I said already ’83, ’84 and ’85 were great years, and most of the woman were older than me. But Lastango’s right. Better to find someone closer to your own age.

    • Lee

      Interesting article…I’d have to say that my most satisfying relationships were with men older than me…one 14 years older, one 19 years older. Jennifer is spot on; I was a weird child. And a weird teenager. And a weird 20-something. I was born when my parents were in their 40′s, so I had a whole different growing-up than my peers who were born to younger parents. Neither relationship panned out for various reasons, but I did marry someone close to my own age who is another “old soul”, which is nice.

    • Megan

      I’m 40. When I was 23 I despised older men, and I still do. Any man in his 40s who is looking to date a 23 year old has issues. He either has a daddy complex or is desperately trying to recapture his youth via a trophy girlfriend. Why would any self respecting 40-something year old, successful person of either sex want to bore themselves with a child? I’ve always dated in my age range. That’s just me. But this advice is borderline psychotic.

    • Megan

      I’m 40. When I was 23 I despised older men, and I still do. Any man in his 40s who is looking to date a 23 year old has issues. He either has a daddy complex or is desperately trying to recapture his youth via a trophy girlfriend. Why would any self respecting 40-something year old, successful person of either sex want to bore themselves with a child? I’ve always dated in my age range. That’s just me. But this advice is borderline psychotic.

      • martesa

        I agree — a 40 yr old man dating a 23 yr old woman is just kinda gross and creepy. I feel the same way about 40-something woman dating a 23 yr old man. In both cases (GENERALLY) it seems like the older person needs his/her ego built up. The younger person either has some issues, or wants money/security/prestige of some sort. Not in ALL case, but in the majority. My husband and I have been together 23 yrs (married 10) and still have a great, fun sex life (I’ve gained some weight due to an illness & the medications, so my self-confidence isn’t always great, but he still treats me like I’m the sexiest thing on Earth, God bless him!) I teach grad school, and I REALLY enjoy my students, but they are such BOYS! My husband also teaches college, & recently someone we know had a relationship with a girl the age of some of the students where he (my husband) teaches, and he was dumbfounded. Although the girls are attractive, he just thinks it’s so creepy to date someone that much younger, not to mention he says he wouldn’t be able to carry on a conversation or laugh with someone that age. I’ve dated a little younger to a little older (although have probably tended towards a little older with both my friends and boyfriends — I’m a bit of an old soul, like jennifer appears to be; my hubby is 4 yrs older) a little taller to a little shorter. It’s all about mutual interests (and the willingness to try things the other person is interested), humor, respect, trust (in life and in bed) and chemistry (again, in life and in bed). I’m not sure it’s possible to have those things with someone when there is a big age gap. And, truly, without those things, I can’t see the sex being good, at least from the woman’s POV (some men tend to think with their little head, so humor, interests, trust may be less important for an affair).

    • Derek Collinson

      What absolute codswallop! Like one of the other commentors I agree that any guy who dates someone young enough to be his daughter has serious issues – probably of the control or ego kind! Better to stick like I did before I met my partner to the plus or minus 10 year rule. I used online dating sites for three years and often received flirts from women the same age as my two daughters and younger but never replied. why else would there be dating sites for mature singles such as http://www.thirdagedating.com. How could you possibly have enough in common with someone from a different era to sustain a deep and meaningful relationship?

    • 2expensive

      Wow when I was 23 I did date a guy in his 40′s and the sex was mediocre at the most. He was very fit and very good looking. Should I have tried it with another 40 year old, maybe he did it wrong. Some prefer it some don’t, for the most part don’t be told by a magazine article who you should have sex. I think intimate relations with someone you know, love, and trust is far more interesting.

      • Ashley Cardiff

        Yeah, I think the crucial thing to remember here is “don’t let magazines (or blogs!) tell you who you want.”

      • Jennifer Wright

        No. You should only want someone who has read Lucetius. Fuck you, Ashley, you are fired.

    • Ship

      As a 23 year old, I was offended by the suggestion that people in their 20s shouldn’t be allowed out. Sure, most people my age are insane, but I like to think I can function in a non-ridiculous way. Then I read on and realised why: I have read On The Nature Of Things. Over and over. In Latin. When I was 17.

      In conclusion, your idea is brilliant and I support it completely.

      • Jennifer Wright

        Join us in the catheter club, stranger-buddy!

    • Mandy

      I completely agree, actually. Men in their twenties are usually idiots. Most people in their twenties are idiots. I’m 27 & just coming out of my idiot stage. Thank the Powers that I am dating an amazing 40 year old who is nowhere near the idiocy of youth.

      And yes, the sex is far better than anything I could have imagined.

    • Eagle Eye

      Eh, I’m a deeply strange 20-something(whose in a relationship with an even more deeply strange 20-something) but I think that I would hate to be with someone older.

      I have 2 extremely parent-y parents (of both sexes) and enough mentors to float a basketball team (well not quite but close) so I feel as though I have plenty of ‘teachers’ i.e. people who have been through life longer than I have and feel like giving me advice and generally telling me what to do.

      The beauty of being with an (admittedly completely brilliant) 20-something is that we’re both really in the trenches together so to speak. We both have these plans for what we want in our lives and we get to figure our sh!t out together.

      I guess, for me at least, when I come home at the end of the day we can either commiserate when things didn’t go as planned or celebrate our successes. Its exciting and invigorating and makes me really feel as though we’re actively building a life together.

      Plus, like I said above, I have enough people telling me what’s best for me, I need my partner to just be there with me.

    • bgrobbins

      Do what you like …….and quit wasting your life telling other people how to live.

      • israel

        hey im a 20 year old male and my 23 year old girlfriend showed me how to bang im pretty sure any woman would love this young very experienced broke ass in the sheets

    • Ara

      As a 23 year old, I don’t think I would attempt a serious relationship with anyone under 27. What a waste of fucking time that would be! …that said, 40 might be too much and even my dad would admit that I have daddy issues.

    • cass

      I got married at the age of 24. My husband was 22 when we married. We have been married for almost a year now and I love every minute of it. All though we have to put starting a family on hold until we finish school and save up more money I wouldnt want to be with anyone else!

    • Geraldine

      I LOVE the cover that is all:
      “MUST LOVE DIE?? 10 ways to save your relationship”

      and then

      “What to do when anxiety attacks”

    • Nina

      No comment on the article just wanted to mention the add I got when I opened this article. The little add was at the bottom of the picture on the first page and it read “Cinderella. Dreams really do come true” made me lol so I thought I’d share.

    • Jenniwren

      Clearly this depends a lot on the 23 year-old. The biggest problem with many guys that age is not so much that they’re idiots, but that they’re all desperately insecure and trying to prove something and tend to come across as very affected in a stunningly inept manner. Like that guy with his “Plato make me want to fuck” line (no-one wants to fuck after reading Plato. No-one, ever). I guess a lot of 23 year-old women act that way too. Now I’m a couple of years out of that age bracket I can look back and go “really? You really think THIS is more likely to get you a date than just being yourself and acting like a human being? And I think that pretense only drops once they’re a little older and have worked out it’s not worth the effort.
      That said, I have met some stunningly pretentious, idiotic 45-50 year olds. Particularly businessmen- the further they get up the ladder the more convinced of their own brilliance they become. So, I don’t know- maybe we should only ever date nice men? And then the other men will start becoming nicer too?

      • Ashley Cardiff

        Oh, my fault. To clarify, he wasn’t saying Plato put him in the mood, he was saying the opposite: that all our highbrow philosophy made him want to do base things.

    • Jamie Peck

      This makes me want to write a very creepy treatise on the beauty of boys. My boyfriend has a baby face and the soft curls of a cherub, and I hope he stays that way forevs.

    • Kyle

      I refuse to date older men out of principle. When older women are able to freely date younger men without being shamed as “cougars”, I’ll change my policy.

    • cjm69

      Coming late to the discussion as I just discovered this, but what the hell. Here’s the thing: Someone you’re dating tends to be someone you *know*, regardless of age (or race, or religion, or gender, or what-have-you). You judge them as an individual, and vice-versa. Whereas someone who someone *else* is dating, especially some random writer online, is just a stranger to you, and much easier to stereotype.

      So there’s a lot of that going on here. I submit that anyone who jumps to the conclusion that any 40something dating a 20something has “serious issues” or is “just creepy,” based on knowing absolutely nothing about the people involved except the ages, has… well, serious issues.

      I’m a guy, and over the years I’ve gone out with women who span a 34-year age range, oldest to youngest, with me fairly near the middle. I don’t regret any of it. And I don’t have any more issues than the next person. I just prefer to avoid pre-judging people based on an arbitrary number. I’ve found that age often has little or no connection with how smart or interesting or thoughtful or fun (or sexy) someone is.

      All things considered, it’s hard enough to figure out our own relationships in life. Why waste time and energy judging and second-guessing other people’s?