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  1. #1

    How to flirt with an older man

    Hey guys. Im 23 years old and im really attracted to older men but i find it hard trying to chat one up, even if its in a shop, Ill see a really fit daddy but dont have the balls to go upto him because all sorts if thoughts run through my head such as what to say and what theyll think with a young guy coming onto them and the fact alot of older men are married . Can anyone help?

  2. #2

    Re: How to flirt with an older man

    Just try saying hi.

  3. #3

    Re: How to flirt with an older man

    im in the same situation but mine is a 57 year old coworker heres my story right here...
    http://www.justusboys.com/forum/thre...3829-co-worker

  4. #4
    On the Prowl ilovebears's Avatar
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    Re: How to flirt with an older man

    do how u would normally its the same thing. although some might prefer u to be more "mature" as in how u act. but some may like tht "young" energy too. it depends on the person rly. i speak from experience as i am currently in a relationship with an older bear and im around ur age too. u can see pics of him i posted on this forum.

  5. #5
    美しいヨーロッパ Scealle's Avatar
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    Re: How to flirt with an older man

    I like guys older than me too. For me it's a bit frustrating because a lot of my classmates/ friends disapproves this and judges me/ thinks that I am weird because of that. Anyway, I think they are normal people like us too. You should try to approach them and talk like normal See how they react.
    Not everyone acts their age I 'd say. My hs art teacher is 50-ish but acts and thinks like a 20 year old. He always hangs out with his students and we all really like him.

  6. #6

    Re: How to flirt with an older man

    Hold eye contact a little too long. If he's interested, it'll send the right message. If he's not, it's subtle enough to disregard.
    xxx-daddies.tumblr.com - Photo blog updated every few hours

  7. #7
    JUB Addict WestCoastWilson's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by Scealle View Post
    I like guys older than me too. For me it's a bit frustrating because a lot of my classmates/ friends disapproves this and judges me/ thinks that I am weird because of that. Anyway, I think they are normal people like us too. You should try to approach them and talk like normal See how they react.
    Not everyone acts their age I 'd say. My hs art teacher is 50-ish but acts and thinks like a 20 year old. He always hangs out with his students and we all really like him.
    Scealle, if I were you, I would get new friends who would support your relationships, no matter how old or young your boyfriend or partner is. Personally, I would not be friends with anyone who does not support me and the boyfriends or partners I choose UNLESS they know something really bad about my boyfriend or partner . . . i.e. he is an ax murderer or something and my friends want to protect me from harm.


    Wilson

  8. #8

    Re: How to flirt with an older man

    It helps if you're around older gay guys in a community sort of activity, like volunteer events where you're doing something relaxing. You'll feel less pressure if it's not some random guy on the street with no context to the discussion. Oh, and stay away from married men.

  9. #9
    JUB Addict kcboi's Avatar
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    Re: How to flirt with an older man

    I agree say hi! We don't bite...

  10. #10
    JUB Addict WestCoastWilson's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by vladislav111 View Post
    It helps if you're around older gay guys in a community sort of activity, like volunteer events where you're doing something relaxing. You'll feel less pressure if it's not some random guy on the street with no context to the discussion. Oh, and stay away from married men.
    I agree with you 100% on your comments, Vladislav111.

    Wilson

  11. #11
    Do I dare to eat a peach?
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    Re: How to flirt with an older man

    Offer to push his wheelchair.

    (Seriously, Vladislav makes an excellent point.)

  12. #12

    Re: How to flirt with an older man

    I'm an older guy (58) who likes younger guys. However, I will never make the first move since so few are interested, and some can be extremely rude even if you are just trying to be friendly. If someone starts a conversation with me then I'll respond. The best line that I ever heard was one time when I was in the local gay bar. I sat down next to a very handsome younger man. He spoke to me and asked if I'd been to the bear event held earlier that evening. I said no, I hadn't heard about it. He looked at me directly and said, "I'm kind of a chaser and I really like older men." He was home in bed with me in about five minutes. It never hurts to be direct.

  13. #13
    ( ̄(エ) ̄) GamerBear's Avatar
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    Re: How to flirt with an older man

    As a younger guy I've found it EXTREMELY difficult to talk to older men, just because they will not find you attractive or you need to be a certain body. A lot of the older men I've chatted with on some websites prefer skinny or young guys who are built.

    I don't fit that description but if you are a cub or chub most of the time you might catch an older bear interested in you. Half the time if its just a regular older man (no affiliation to bears or chubs) might be a slight chance they will be interested in talking to you. Not sure because if its rejection that makes older men more picky to who they talk to or if its just sexual preference.

  14. #14
    Newbie alan518's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by GamerBear View Post
    As a younger guy I've found it EXTREMELY difficult to talk to older men, just because they will not find you attractive or you need to be a certain body. A lot of the older men I've chatted with on some websites prefer skinny or young guys who are built.

    I don't fit that description but if you are a cub or chub most of the time you might catch an older bear interested in you. Half the time if its just a regular older man (no affiliation to bears or chubs) might be a slight chance they will be interested in talking to you. Not sure because if its rejection that makes older men more picky to who they talk to or if its just sexual preference.
    FUCKING THIS

    Even though I am losing weight, that's how things are

    The guys I am attracted to( the older, chubby, manly acting men) are into twigs. It sucks because most likely those twigs are not attracted to older men.

    When I finish with my weight loss journey i'm going balls deep in older men this year lol

  15. #15

    Re: How to flirt with an older man

    Quote Originally Posted by phil1715 View Post
    Hey guys. Im 23 years old and im really attracted to older men but i find it hard trying to chat one up, even if its in a shop, Ill see a really fit daddy but dont have the balls to go upto him because all sorts if thoughts run through my head such as what to say and what theyll think with a young guy coming onto them and the fact alot of older men are married . Can anyone help?
    You could walk up to him and say "I'm horny, tight and would like you to fuck my brains out!" I'm over 50 and that always works with me.

  16. #16
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    Re: How to flirt with an older man

    I am interested in older men as well. Always have, always will, until I am older myself .

    Anyways, older men usually love when a younger guy comes up to them, it makes their ego feel good. Now however in some cases older men (any man) will like someone more in shape. Don't take offense to it, its just not what he likes.

    I myself am seeing a guy who is 56 and im 26. When him and I first met on grindr/scruff he told me that he is usually into twink/built type guys and who knows if anything will happen, let it flow he also said. I myself am 215 5'10", overall I hold my body well, however I do have fat, main parts being stomach and thighs. (Working on it, down 10 lbs so far ). Anyways, clearly I wasn't his type and the only reason which I just found out recently on why he met me was because he was pissed at someone who said no don't meet him (me), so he went against the person. This was back in August/September. We have been seeing each other almost on a daily basis ever since. As of recently he has been staying with me while he is in between places, which he leaves this friday =(.

    The point of what I am saying is, is that he grew to me and my personality over my body type. Say something, show your confidence. Confidence can be the sexiest thing. A hello can go a far way. The problem with a lot of guys, is that we don't express what we feel, we hide it and play games to not hurt ones feelings. I'm sure you'll find plenty of older men. Just open up .

  17. #17
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    Re: How to flirt with an older man

    Quote Originally Posted by palemale View Post
    You could walk up to him and say "I'm horny, tight and would like you to fuck my brains out!" I'm over 50 and that always works with me.
    I don't know if I'd say all of that unless the guy is hot and I know he would fuck a guy. lol

  18. #18
    ( ̄(エ) ̄) GamerBear's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by alan518 View Post
    FUCKING THIS

    Even though I am losing weight, that's how things are

    The guys I am attracted to( the older, chubby, manly acting men) are into twigs. It sucks because most likely those twigs are not attracted to older men.

    When I finish with my weight loss journey i'm going balls deep in older men this year lol
    I found my hubby here on JUB, he's 52 years old and he definitely likes my body and likes me for me. I may be chubby but it indeed sucks when most older men only like twinks.

  19. #19
    On the Prowl ilovebears's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by GamerBear View Post
    I found my hubby here on JUB, he's 52 years old and he definitely likes my body and likes me for me. I may be chubby but it indeed sucks when most older men only like twinks.
    im curious about the word twinks. are all skinny gay men considered twinks? or is it purely used as a derogatory term?

  20. #20
    CupidBoy
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    Re: How to flirt with an older man

    Ask if they'd like to play Canasta and talk about the good old days.

  21. #21
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    Re: How to flirt with an older man

    Quote Originally Posted by ilovebears View Post
    im curious about the word twinks. are all skinny gay men considered twinks? or is it purely used as a derogatory term?
    No its not used as a derogatory word. The gay community has MANY names for different types. Twinks are on the thinner side and usually range a bit younger.

  22. #22
    On the Prowl ilovebears's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by Storybook_Man View Post
    No its not used as a derogatory word. The gay community has MANY names for different types. Twinks are on the thinner side and usually range a bit younger.
    cuz sometimes people use it as a derogatory word for the overly flamboyant right?

  23. #23
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    Re: How to flirt with an older man

    I have heard people use Queen and Bitch for the overly flamboyant but never twink.

  24. #24
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    Re: How to flirt with an older man

    i'm in the same situation almost. I was at the local square, it's quite known about the hook up scene there, so i was sitting at a bench and opposite to me comes this sexy daddy, around his 40-50s grey hair, little belly, and very handsome for his age but far from trendy, he was a real man!!! He knew i was checking him out so he smoked a few cigarettes to take his time, we exchanged a few stares and i knew he wanted to take it further, but as the place was busy he decided to leave passing right in front of me giving me a stare that i felt it was meaning lots of things, then he went to sit at a cafe which was busy enough. Did he mean he wanted me to join him or he was just fed up by the crowd?! I'm really confused and in the same time very very interested in this man.
    Last edited by tiesilk; June 11th, 2013 at 01:27 AM.

  25. #25
    On the Prowl droopyd's Avatar
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    Re: How to flirt with an older man

    Quote Originally Posted by kcboi View Post
    I agree say hi! We don't bite...
    Unless you ask real nice!

  26. #26
    Are u haleloo ya ? Telstra's Avatar
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    Re: How to flirt with an older man

    Old guys don't like younger guys for one thing only.
    Most young guys don't know how to clean their foreskins and ass ...


    NEVER LISTEN TO A ONE SIDED STORY AND JUDGE.

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    Re: How to flirt with an older man

    Quote Originally Posted by tiesilk View Post
    i'm in the same situation almost. I was at the local square, it's quite known about the hook up scene there, so i was sitting at a bench and opposite to me comes this sexy daddy, around his 40-50s grey hair, little belly, and very handsome for his age but far from trendy, he was a real man!!! He knew i was checking him out so he smoked a few cigarettes to take his time, we exchanged a few stares and i knew he wanted to take it further, but as the place was busy he decided to leave passing right in front of me giving me a stare that i felt it was meaning lots of things, then he went to sit at a cafe which was busy enough. Did he mean he wanted me to join him or he was just fed up by the crowd?! I'm really confused and in the same time very very interested in this man.
    Should have approached him. Seemed like he wanted to sit and talk and go from there.

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