Older woman, younger man

Discussion in 'Sex, Love & Relationships' started by Frank Holton, Jun 18, 2011.

  1. What might be some issues involved with dating a woman twice (and maybe a couple extra) my age?

    As reference, I am 24, she is in her mid 50s - although she easily looks like she's thirty-something.

    On my end there are a few concerns:
    1. I'm moving to Seattle in about two months so I'm looking for a, more or less, casual fling
    2. She is divorced and has a daughter (unsure on age, but I suspect she is young)
    3. I recently asked her out for drinks, to which she replied that she would think about it

    Possible concerns on her end:
    1. Image of herself dating a younger man, one that could easily be her son, and the pressure from family and friends for this choice
    2. Am I mature enough for her
    3. Timing and the issue of possible attachment, and maybe heartbreak because of me disappearing so soon
    4. Will my appeal toward her change should things become more intimate - as in how could sex change things, will she feel desired given the age difference and aesthetics

    Obviously I am incredibly, nay, undeniably attracted to her. She has some of the most pulchritudinous eyes that I have come across. Not to mention her intriguing knowledge of hip-hop. Sure she is slender and has a kickin' rear, but when she around my heart quickens ever so slightly, and inevitably, I become quite aroused. Hell, I often find myself secretly glancing as she walks by, hoping in some way to catch her eye.

    I digress... I work with this woman and, while I see her nearly everyday, it was only recently that I have had any thoughts concerning something more than simple professional relations. Yet, for some reason I believe this is brought on by my upcoming move and my desire to lavishly romance a woman.

    So any advice on a proper or more seductive approach?
    I'm still awaiting an answer from her
    • Like Like x 1
  2. :eek: All I can think is how my mum is 50 and you're screwing a woman who is 55?

    40-45 is a cougar, 55 is a dinosaur imo.
  3. I got one word for ya: "Yuck"

    *insert puking smiley here*

    Dude your 25....the chicks your age are smoking hot and prime...there will come a time like in the next 15 years you'll never be able to get a beautiful young women again.....take advantage while you can...there will be plenty of 50 year olds when your 40.

  4. That's SO COOL, you can enjoy the benefits of "senior citizens" discounts while on college "Spring Break"
  5. Her "I'll think about it" = "no way dude, you're to young."

    If she was game, she would have already thought about it and would have said yes.
    • Like Like x 1
  6. First off, she is mature and if she knows you are moving, she will know what you are expecting/wanting.. If It means anything she probably already knows if SHE wants to go out with you but she is probably unsure of maturity, compatibility, and definitely won't bring you home to meet the child.. All you are able to hope for is a yes and maybe a shag, but cut the crap about how whatever word her eyes are. We know you are trying to sound intelligent and make yourself look better , important thing is.. So will she.. Your best chance to 'score' would be to treat her like you would any woman on a date and talk to her the same way.. She probably would just want to get away from the house and kids, but doesn't want to be around horny, begging 20 something's.. So don't act like it lol
  7. older women love to fuck..

    no games, no texting, no facebook drama.. just fucking.

    enjoy dude.

    if you're looking for a serious relationship beyond just fucking.. then forget it, because older chicks who are single are also pretty insane.
  8. Do you really want to be screwing a 71 year old when you are 40?
  9. the idea of hooking up w/ an older chick is not to spend 30 years with her.
    trust me, a 50 year old doesn't want a 30 year realationship.
  10. cover the face and f*** the base. words to live by ;)

    MOAR SKIN FOR THE WIN (i think i just made that up)
  11. If you haven't fucked an older woman you really haven't had sex.... they have skills, many, many skills.
  12. You should go for it. I doubt very much she is looking for a long term thing and perhaps your impending move makes you more attractive to her because there is an end point defined.

    I suspect what she wants is sex (and it will be good I assure you). What she is afraid of is work or personal implications such as her child finding out.
  13. crazy in the head, crazy in bed :ey:

    but really, i'm 21, and i would LOVE to bang a 35-40 year old
  14. Is there a way to appropriately touch her in the workplace to show interest - something that won't have me fired over sexual harassment?

  15. Dick in a box
  16. [quote name='"[[jamminout']]"]

    Dick in a box[/quote]


    please I beg someone reps this guy for me.
  17. +rep for using pulchritudinous.

    Beautiful use!
  18. thats a little to old for a relationship. but if shes decent, id hit that.
  19. Be upfront about it. I'm sure if she is into you she would appreciate that.

    Just tell her you're attracted to her or something like that. I'm use to dealing with younger, more immature girls, so I wouldn't be able to predict the reaction of someone 50+. If she isn't diggin you she'll let you know, and then its over with.

    But hey, if shes a cougar, then go for it.
  20. I keep on seeing really hot older females with nice bodies all over the place! I don't know what's happening but women keep on aging better and better. I remember when 40 was ancient, now a $hit load of 40 year olds are looking better than ever, (and you know they're in their sexual prime!) especially here in Cali. Jen Anniston, Demi Moore, Halle Berry, Marisa tomai, Sofie Marceau etc. all look really good.

    Women over 40 who are still smoking hot, a gallery :WagerWeb Entertainment


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