The Pros and Cons of Dating an Older Man
  • Posted Apr 25, 2014
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There is a fine line between hot and Hefner.  Recently we have seen the media portray age-gapped relationships in a variety of ways. With gossip staples like Courtney and Doug there are a variety of thoughts on these sometimes controversial relationships.


Dad or date?

Realizing your new boyfriend is just a few years younger than your father is a harsh reality.  Remind yourself what ignited this initial attraction and focus on that.  After all, there is something innately sexy about a silver fox.


He inevitably has a few years on you – professionally and personally.  You might love his deep pockets, but with his great power comes your vulnerability.  There is potential that you could never be financially equal to him, accepting this is key.


You may need to start skipping the traditional Thursday through Sunday bar scene with the girls to appease his lifestyle.  While this may seem like a much-needed break, there is potential for you to end up at a home-dinner party socializing with a group that may tell you about their son or daughter that is “just about your age.”  Awkward.  Try to create a balance.


Dating someone 20 to 30 years older than you means you’re probably going to see time take its toll in many ways.  When the allure of dating someone new wears off, it’s important to accept your partner for the person that you met – even if they are 20 years your senior.



An older man usually has an established work, social and home life.   As a younger, or transitioning individual, this stability may be exactly what you need.


Money honey!  Drinks, dinner, and gifts all on his dime.  Older men are often looking for something consistent. You can be sure that he won’t play games like millennials, since he’s past his prime player years.


The more experienced, the better.  Mature men have refined tastes, and that isn’t limited to his pallet.  He can show you things you never knew possible, and you can teach him that new trick you learned in Cosmo.


Older men are more old-school about courtship.  You won’t be dealing with the same texting, mixed signal bullshit that you’ve experienced in the past.


You’re going through something stressful?  Chances are he has been there too.  Advice and wisdom will be readily available from someone who isn’t your parent, but is equally wise.


You will never feel more wanted in your life.  Your body next to his will feel like a temple.  You won’t catch yourself with lingering thoughts of other lovers or competition.

Remember:  in the wise words of Aaliyah, “Age Ain’t Nothin’ But A Number.”

What’s your favorite thing about older men?

29 Responses to “The Pros and Cons of Dating an Older Man”

  1. Cristina says:

    Quality older men feel great to me. They are settled in their personality and character. Solid. Established. They can give you advice. The biggest thing is that they are solid & mature. I luv having dinner & conversations with older men. “A single conversation across the table with a wise man is worth a month’s study of books”… very true!

  2. DarkHorseSD says:

    Need me to write an article “The Cons and Cons of dating a younger woman?”

  3. Jersey Darling says:

    I’d expect to find this article on SA. In my experience, most of the men on WYP are far younger.

  4. Josh says:


    How about “The Cons and Cons of dating a woman?” LOL!

  5. The Truth says:

    I liked this article. Older men are much better than little broke punks that think they are cool.

  6. Jenny Alaniz says:

    We cant help who ourvhearts love

  7. Mostly correct. It is amazing not having to take care of myself… however, the sex part… He does know some tricks, but the stamina is lacking. He doesn’t have his 20 year old body anymore. That’s all I had to add.

    • lol says:

      lol. maybe its just that guy. im 18 and my bf is 34 and he has more stamina than any guy ive ever been with.

    • Tiana says:

      It all depends on the person. I am 23 and the love of my life is 49 and he has great stamina. We stay active together, workout, encourage each other to eat well, and sometimes his sex drive is even higher than mine.

  8. Tom says:

    Funny article. it shows a lot of the author. I thought we are in modern cultures where age doesn’t count. But it seems not every culture is on this step yet.
    Noone asks how old you are because it doesn’t matter.

  9. ugh says:

    this is a great article except you could have picked a song that didn’t have underage sex vibes. ugh.

  10. ExoticCandi says:

    I enjoy older men. I usually attract younger, cocky guys that do not know how to treat a woman. Lately, I have been attracting more older guys and I find that I like the maturity, conversation, I can tell them my 1-5 year goals and they get it.

  11. j says:

    Age does matter. Take dating an older men at least 15 yrs your senior, they tend to give lectures about every little thing you shouldn’t do and sleep by 9pm every night. Yikes!

    • Tiana says:

      Everyone has their opinion on age difference in a relationship, but the theme I’ve come across in it all is that if you love each other unconditionally than everything else shouldn’t matter. My boyfriend is 26 years older than I am but we have never loved and trusted anyone more.

  12. in love and confused says:

    I love my boyfriend who is few years older than me, but I just found out his weird kinks recently and am confused as have grown to love him too much,he loves to suck dick once in a while n always expresses to see other dicks fuck me, it’s a turn on for him.. .am confused as I don’t know what to do and I love him completely. .toldh him I’ll give it a try once with a threesome. that weird?

    • Dale says:

      A man that loves and respects you will not ask this. Start looking for another boyfriend who can focus on you.

    • Mary says:

      Any man that loves to suck another man’s dick is gay why should you settle for that you’re better than that you need your own man where you don’t have to share him sucking somebody else’s dick

  13. Ms thomas says:

    At first i loved my older man ge gave me things we went out.i got preganet left him cause the living situation wasnt stable came back after our son was born.again the living situation went bad hes made theses promises to me.going in 2yrs im going my money.but he keeps going out with his old.buddies thats means him no good. He want listen to me treats me like im a child. Im 6 mths preganet. I planned on leaving things not working out

  14. Nomae S Sithole says:

    Am also dating a guy who is older than me and I love him so much.

  15. Tosh.O says:

    I am personally 26 years old-dating a guy that’s 65. Here’s the thing though… he’s stable, non -controlling, super intelligent, he was a war vet, he’s financially stable. Believe it or not, him and I have a lot in common personality wise. I grew up way too quickly with hardships, but also got the major partying stage out of my system. I’m sort of a loner, but it’s great being with someone that I can really rely on and trust. I don’t have to worry about him cheating on me, because he absolutely adores me-and treats me super sweet. He isn’t needy, he’s wise, and honest. I know what society says, but I don’t care. I can spend all day in his arms, and I really do love, and would marry this guy. Plus, I don’t have to put up with the crap that used to get to me with younger guys. Immaturity, sociopaths, cheating, neediness, likes..the list goes on and on.

    • Future ms. Kelley says:

      I have the same thing you do with your love…i am 38 and my lover is 60, he makes me feel a certain kind of special that no one had ever made me feel…the sex is amazing and his arms around me just feel like paradise. We were together 7 years ago but circumstances took us apart and now we have recently found our back to eachother rekindled our love even brighter than before!

    • Mary says:

      He’s a keeper go for it

  16. joseph otoole says:

    WELL DONE you sound happy

  17. RagDoll says:

    Im 20 the guy ive started to see is 45 as of a couple days ago. My folks raised me so old school. That i know im a old soul and enjoy the company of adults older then myself. I’ve never thought about his age when i first met him i thought he was late 20’s early 30 maybe… A few weeks later finding out hes 44 at the time didnt freak me out he acts like hes 25-30 but is nothing like how my folks are. Hes always looking out for me, helping me doing the little things guys my age never thought of before its so wonderful. Despite how happy i am and how much hes helped me my mother seems to hate hate him even tho she’s never givin him the chance for her to get to know him… I love my mother. But shes sooo stuck on that number… Is there anything i can do to help make her see or have an open mind to what’s going on. Im so lost when it comes to this. All i know is i don’t want to give him up but making my mother cry isnt the high light of my day either… Thank you for this blog about you and ur beau. It was a much needed read knowing other people are in the same boat i am in now and that it’s ok 🙂

    • Robert says:

      RagDoll: Ask yourself the questions:
      – With who will going to live? Your boyfriend or your mother. Mother(parents) deserves all the respect, but it is your life and you are the one to make a choice. Risky or not, it is you who need to live your life and have first hand experience. And you should talk with him.

      I am about his age, so I can imagine how he feels awkward under the look of your mother, but will probably respect your decision. It is situation that is not common, so it is reasonable to understand a bit your mother’s reaction, but it is your life. And you need to own it.

  18. Christy says:

    I love my man but he’s 30 years older than me. I’ve never been the type to go after older men but when we met we connected. But now almost a year later I feel like that connection might be fading. Which sucks because I’ve got my first little one on the way. Of course my parents don’t approve. I never knew anyone could frustrate me so much . He literally tells me that he doesn’t have to listen to me because there’s nothing he can learn from. He’s so arrogant. Ugh help me please!

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