Home / Adult Dating / Survey-How old is the oldest person you’ve dated (biggest age difference) and did it work out?

Survey-How old is the oldest person you’ve dated (biggest age difference) and did it work out?

I’m curious and wonder if there is other people out there I can it relates to this topic, before you start judging and Being immature, We are both adults, so serious answers only please.


  1. Detective L is the bday boy Oct 08

    today i am 19 yrs old and my boyfriend is 23 turning 24 in december…
    so far its going well

  2. 4 yrs older, not really but we’re friends still

  3. Four years.

  4. well,

    i want to date a girl half my age, she would still be over 21,

    Prowling wolf and wily fox

  5. I was 13 and he was 38. It didn’t last very long. The longest relationship was a 3 year difference.

  6. When I was 18 I dated a 26 year old. Didn’t really work out.

  7. im 19 by bf is 25
    i guess its alright so far

  8. hmm. he was 7 months older, and no it did not work.

    then i dated a dude 15 days older

    now im happy w one (maybe lol were jst friends ..) 13 days younger

    im not rushin this cuz i want a nice good solid stable friend relationship to base any romance upon haha.

  9. sαναnnαн мαяιє .

    i was 17 , he was 31 .
    i know , i know . it sounds gross , but he didnt look or act 31 .
    welp , i was a virgin before i met him && hadnt been in a serious relationship , spent most of my time wit him && started fallin for him , when he took my virginity that was iT , he had me hooked .
    he was VERY manipulative , i hadnt been in a relationship before so he knew how to manipulate me ; i hadnt had my heart broken before , but he had been through many relationships including a divorce , so tha problems that we had affected me 100 times more than they affected him .
    i love him to today still .
    but i hate him for dating me when i was still so innocent && doing me tha way he did . he knew better , he should have never messed wit me because he was an adult && i still had such a childish way of looking at things , he knew that too .
    i lived wit him & basically was part of his family , raised his kids at 17 . it took a toll on me dude , trying to be so mature when i wasnt , it made me grow up A L0T .
    thats tha bad thing wit such an age difference ,
    youre at C0MPLETELY different places in life && it doesnt work usually , so if youre young && it was your first love . its tha hardest thing youll ever have to do .
    it didnt work out , of course , we dated until here recently .

  10. I was 14
    He was 21
    We lasted like 3 months, he was a total creep and now that I’m 18 I realize he was a loser. It did not work out. At 14 you just want to date an older guy to be cool, but I still have nightmares about him time to time…

  11. The relationship I’m in now. I’m 20 and my boyfriend is 36. The relationship is going quite well, I must say.

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