I am in my 50s, haven't dated for decades. do women care what kind of underwear a guy wears?

Update:

My wife of 35 years died and plenty of women seem interested. But dating is very nerve wracking for me.

Update 2:

I am am a  clean freak.

20 Answers

Relevance
  • David
    Lv 6
    1 month ago

    I'm in my 50s.  For the past 30 years, my girlriends (and two wives along the way) greatly preferred me to not wear underwear at all.  OK, so you go out in public for a date or something.  You wear underwear then.  But as soon as you get back to the house, the clothes and underwear go flying in random directions.  And when you are in bed, wearing underwear is a really bad idea for both of you.  It just gets in the way!

    When you are away from home, out in public...it won't matter to your girlfriend what type of underwear you wear, as long as it's clean..

  • Anonymous
    1 month ago

    Sorry for your loss :(

    Regular briefs works for any body shape, boxer briefs are nice too. Hip briefs are sexy but not over the top.

    Stick to solid colors or ones with strips.

  • 1 month ago

    just please don't wear tighty whities

  • 1 month ago

    Clean would be the only thing I'd expect.

  • How do you think about the answers? You can sign in to vote the answer.
  • Mary
    Lv 4
    1 month ago

    Heck no, they love smelling underwear with holes in them and greyish brown in colour

  • Anonymous
    1 month ago

    I am a female in her 40's.  As a rule I don't care about the underwear a guy wears.  I think boxers are funny looking, but maybe that's just me.

    I'm more impressed if a guy in his 50's can obtain and maintain an erection.

  • Anonymous
    1 month ago

    Yes, by that age you may be wearing disposable diaper briefs so yes, it matters unless you have a good tight behind that can wear a G-string. Otherwise, I would be worried about your personality over underwear.

  • Foofa
    Lv 7
    1 month ago

    Only if they see it. So if you're going to splurge on fashionable underpinnings you likely won't need it until the third date ;-)

  • Anonymous
    1 month ago

    I'm in my 30s, so not sure I'm any help. But, I honestly can't take "tighty whities". As long as my husband sticks to his boxers or boxer briefs, I'm happy.

  • 1 month ago

    News flash: Some care, some don't, and some have particular preferences. Why? Because every woman is different and has different tastes. If you imagine that all women are the same, as your question implies, this might explain why you haven't dated for decades.

Still have questions? Get your answers by asking now.