I'm a man who likes to drive with high heels on...

I call it drag racing.

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πŸ‘€︎ u/Striddy2
πŸ“…︎ Apr 27 2018
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I just got new high heels....

...and since I directly fell in love with them, I had to send a photo of me wearing them to some friends and somehow also my to dad.

I got responses like "You look hot" or "So sexy!".

My dad's response: "You must be so tall wearing them. I guess I know who's getting a helmet for christmas!"

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πŸ‘€︎ u/drakooi
πŸ“…︎ Dec 13 2015
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Got my girlfriend with this today, her 13 year old sister just bought her first high heels.

Her: "she's too young for heels, like where's she going to wear them?" Me: "on her feet"

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πŸ‘€︎ u/roryo
πŸ“…︎ Sep 28 2015
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What do you call a milk man in high heels?

Dairy Queen...

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πŸ‘€︎ u/gabrielc0208
πŸ“…︎ Jul 25 2017
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Learning to walk in high heels will keep you on your toes.
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πŸ‘€︎ u/ImEnhanced
πŸ“…︎ Feb 22 2018
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What do you get when you have a high heel fetish and see a real nice pair of stilettos?

A shoe horn

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πŸ‘€︎ u/hmhammersmith
πŸ“…︎ Jul 30 2017
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My wife went to get a pedicure with her mother. She sent me a text saying that they have an exfoliating, foot scrub that has CBD/Hemp oil in it and she was going to try it out...I replied β€œbaby, do you realize that you left the house with slippers on...

But you are coming back with high heels”. Her mom sent me a text asking me what I said that made my wife throw her phone in to her lap and groan aloud. Mission accomplished haha

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πŸ‘€︎ u/SirTurkTurkelton
πŸ“…︎ Jan 29 2020
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I went to a drag race last Saturday...

I still can't believe the guy in high heels won.

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πŸ‘€︎ u/jigsatics
πŸ“…︎ Oct 02 2020
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My wife never saw it coming...

I got my wife with a rather unexpected dad joke last night.

I generally don't like surprises, with only a few exceptions. Last night, I come into the bedroom and she is wearing a white corset, matching panties, knee high socks, and high heels.

She asks "Is this the kind of surprise you might like?"

I respond with a big dumb grin on my face, "Of 'corset' is!"

It almost cost me a fun night, but it was worth it.

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πŸ‘€︎ u/blackdragon8577
πŸ“…︎ Sep 09 2014
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Dad Joked the entire room

Sitting in the living room talking about the appeal of nascar with the family when my step mother said she liked the drag races more. Without missing a beat I popped off with: I've never understood the appeal of watching grown men in high heels running down the street.

It was the best part of my day to watch everyone in the room pause, turn slowly toward me and groan loudly

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πŸ‘€︎ u/Intega
πŸ“…︎ May 09 2014
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What type of shoes...

Did the ninja wear, sneakers. Did the hippie wear, high heels. Did the gymnast wear, flip flops. Did the pornstar wear, pumps. Did the server wear, waders. Did the Yogi wear, none he has bear feet, Boo Boo.

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πŸ‘€︎ u/PaxPaw
πŸ“…︎ Jan 28 2018
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Why are support characters in video games always female?

Because they have high heels.

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πŸ‘€︎ u/Dapolish
πŸ“…︎ Apr 27 2017
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My Little Pony gone wrong

My sister posted about loving my little ponies, and we got on the topic of rainbow horse poop jokes. My dad just pops in with this:

Dad - I can't think of one right now. I do, however, have a poem that is somewhat related: (first assume standard high-class poetry recitation position; head high, chest out, hands clasped behind back, heels together, toes @ 180 degrees, knees slightly bent): "In days of old, when knights were bold, and toilets weren't invented; they left their load beside the road, and went away contented."

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πŸ‘€︎ u/heidibearmommacat
πŸ“…︎ Dec 10 2015
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My friend got me pretty hard while I was in heels

I was wearing high heels, which is unusual for me, and talking with two friends when I said, "Hey [Friend 1], I'm almost taller than you!" (I'm a shorty, 5'2")

Friend 2, "Nah Brunchy you still have a lot to go"

Me, "Well then these heels are pointless."

Friend 1, "Yeah they have a rounded front."

She's going to be a fantastic dad one day.

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πŸ‘€︎ u/brunchfordinner
πŸ“…︎ May 03 2014
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