20 Differences Between Dating In Your 20’s And Dating Over 50

© Lisa F. Young/Dollar Photo Club

When it comes to relationships and dating, someone might think things don’t change as much as you get older. A woman meets a man, they like each other and they decide to start a relationship – this never changes, no matter how old you are.

However, the little things are completely different. Let’s check out a list of 20 things related to dating, and just how different they are when you are in your 20’s and when you are over 50.


Do her parents let her stay out late?
Will her kids ever stay out late so we can have the house for ourselves?

Will she laugh at my fancy hairdo?
Will she like the hair on my back?

I hope she isn’t too emotional and needy.
I hope she has a functional thyroid.

If we have sex, how long will I be able to last?
If we have sex, how long will it take me to start?

Will I be able to hold her hand?
Will I be able to hold my pee?

Let’s go out at a dark, mysterious place and have a romantic dinner.
How am I supposed to read the menu with so little light?

Oh, wow, she’s not wearing a bra!
Umm, oh, she’s actually not wearing a bra…

Does she think my Mohawk is sexy?
Does she notice I have a comb-over?

I wonder if she’s on The Pill.
Does she wonder if I’m on The Pill?

Please, please, please have sex with me.
Please, please, please have sex with me.


I hope he walks me home.
I hope he has a healthy hip.

Will my parents think he’s a nice guy?
Will my kids think he’s a nice guy?

Oh, shoot, he just wants to be friends…
Ok, how about friends with benefits?

I wonder what style his pubic hair is.
I wonder if he has hair growing from his ears.

I hope he finds my heels sexy.
I hope I don’t have to wear heels on every date.

I wonder if he’s flexible enough.
I wonder if he’s flexible at all.

I hope he doesn’t have a psycho ex-girlfriend.
I hope he doesn’t pay high alimony.

I’m totally confused about how to tell him it’s over.
“Sorry, this doesn’t work out for me. Have a nice life.”

I wonder if he drinks too much alcohol all the time.
I hope he’s allowed to drink alcohol.

Will it ever go down?
Will it ever go up?