Dating as a Teenager vs. Dating as an Over 50

A lot has changed for us Over 50’s since we were teenagers.  And some things have stayed very much the same.

In regard to dating, relationships, and sex, here’s a look at what men said, thought, and worried about back when they were teenagers, and what they say, think, and worry about now that they’re Over 50: 


Will her parents let her stay out late?

Why don’t her kids ever stay out late?


Will she let me get to second base?

How long after her mammogram ‘til I can touch her boob?


Will she laugh at my peach fuzz?

Will she laugh at my back hair?


I hope she doesn’t have mononucleosis.

I hope she’s got a functional thyroid.


Can I get her into the back of my van?

Can I get her into the front of my Smart Car?


If she lets me have sex with her, how long will I be able to last?

If she lets me have sex with her, how long ‘til I’m able to start?


Can I hold her hand?

Can I hold my pee?


Thank God for Midol.

Thank God for Estrogen cream.


Let’s go to dinner at that dark, romantic restaurant.

Who can read the menu with so little light?


I wonder what shade her pubic hair is.

I wonder what style her pubic hair is.


I’m really dreading telling her it’s over.

“Sry. It’s not you, it’s me. G2G 🙁 ”  [SEND]


Does it ever go down?

Will it ever come up?


Oh my god, she’s not wearing a bra!!

Oh, ehhh, she’s not wearing a bra…


I hope her parents will like me.

I know her kids will love me.


Oh, shoot, you just want to be friends?

Oh, okay, but how about friends with benefits?


What I wouldn’t give to date Christie Brinkley.

What I wouldn’t give to date that cute barista.


Sorry, but would you mind chipping in for the gas?

So how about we just split an Uber?


Will my Mohawk excite her?

Will my comb-over fool her?


Do you know anyone who could score us some weed?

I’ve got a card so I’ll stop by the dispensary.


I wonder if she’s on The Pill.

I wonder if she wonders if I’m on The Pill.


It’s so cool that her parents gave her a credit card.

It’s so cool that her pre-nup got invalidated.


I cannot wait to see her naked.

We both want the lights off, right?


I hope I can find her in the phonebook.

I’m sure I can find her on Facebook.


God, it is so embarrassing to ask the pharmacist for condoms.||“condoms”||Trojan Magnum||Buy now with 1-Click®


Please, please, please touch my penis.

Please, please, please touch my penis.