Dating advice. Older women?

[BigHornRam]

Note to self:

Don't come to this site looking for Dear Abby advice.

Her name wouldn't happen to be Maggie, would it, Doug?

 

[QuazyQuinton]

Somewhere in another corner of the internet, perhaps a medical practitioners discussion board, there is a thread titled "Dating advice. Younger men?" I wonder if it has gone off the rails as badly as this one.

QQ

 

[westbranch]

No personal stories from me. But a friend in his early 20s met a mid 40s cougar and had a few weeks summer fling. Her name was Donna so his friends referred to her as Donnasaur.

 

[noharleyyet]

...lest we stray from the thread's comedic utility.

 

[stk]

Alright so my main thang from last year decided she’d rather go back to the bar scene than live the monastic, disciplined life of a western bow hunter that I tried to show her.
Is what it is.
She’s a cool chick, but weak men stand in crowds whilst strong ones stand alone.

Which brings me to the matter at hand.
Around the same time I met the girl mentioned above, I met this 52 year old Vanderbilt n.p.
We’ve hung out on and off for the past year.
She even skied a couple laps with me this winter when she was out seeing friends.
She was phenomenal on the greens, but it took us about 2hrs to get down from the top of super bee and I was really worried her or someone else was gonna die.
Honestly, I really thought I was just working for her as a pool boy, but we’ve been hanging out more this summer and she’s even asked me to meet her parents and friends which I have been unable to do because of scheduling conflicts.
There’s definitely some weirdness with the age gap.
I find her to be a very attractive women, if I was 40 or 50 I’d be proud as shit.
But last summer we were getting dinner and when she got up to use the restroom, the very attractive 20 something waitress asked me if she was my mom or girlfriend and it was odd. (Nosy bitch) lol
Obviously I wonder what the future would bring if I was 50 and she was 70, but we’ve all seen how good @noharleyyet , @JLS and @MT Rookie aka OR Chris look.
Modern medicine and lifestyle have really altered the effects of aging in this country.
One obvious benefit of dating this seasoned, Vanderbilt educated, medical professional is that in the future, if @wllm ’s complaining about his wife’s student loans or the hours she’s working I can always be like “hey kid, stick with it. It’s gonna pay off once she gets some experience under her belt” and I can send him pictures of me in her ex husband’s bathrobe standing in front of her subway tile backsplash and glass door shower in her baller ass house.

But yeah, I’ve bounced these thoughts of the irl homies and they seem to think that as long as she’s not asking her to kill her ex husband, i should see where it goes.

Just wondering what you guys and gals thought of the situation.
Thanks for any help and feedback.
Happy Friday!

Do whatever you want, but if you want to go meet her parents like she asked, you should probably do it quickly.

 

[R.K.]

You're all absolutely horrible. Thanks for reminding me I'm a terrible human- I owe you all a beer.

And I'll just leave you with this- it's a terrible idea, but when has that ever stopped you?


P.S.- apologies to the Mrs. BigFin on behalf of all of us, for having to read this. Thanks for tolerating this bunch of miscreants.

 

[Hilljackoutlaw]

Summers from roughly 11-15 years old my neighbors Deb and Sherri lived in the apartment house right next door. One in back one in front. They would sun tan like everyday in bikinis. I'd throw grounders to field off the foundation of the garage and day dream. Fast forward 8 years or so. I swing into the watering hole on a Saturday after work at the golf course all grassy and sweaty in July. I'm on my second beer talking to Brucey the bartender about hitting the river tomorrow and do some muskie fishing and who sits down next to me none other than sweet Deb who just happened to be in town for the weekend.



I did go fishing just not for muskie.

 

[seeth07]

At least you won't have to worry about her calling out the wrong name during sex or thinking/ pretending you are someone else. All her ex's be like:

 

[Addicting]

I didn’t take the bait…was in a serious relationship and still happily married to my HS Sweetheart. But damn, she was really messing with my young head….damn cougars

If you’re in a serious relationship and still married then you have the skills to take on one more for Christmas, slacking man…

 

[Addicting]

The user name Oedipus is still available if you are interested in changing.

 

[Redmt]

If you’re in a serious relationship and still married then you have the skills to take on one more for Christmas, slacking man…

He needs to write a book.

 

[The Hedgehog]

Her name was Donna so his friends referred to her as Donnasaur.

Amongst a small group of my pals years ago there were ladies known as Skeletor (skinny), the Crypt Keeper (old), Bonesaw (braces), dumb Terri (dumb), Peter pants (wet her pants when drank too much), tits Magee, crazy eyes, and I’m sure others I’ve forgot.

 

[BigHornRam]

So who's currently in the lead? Devil Doug or angel Doug?

 

[fishing4sanity]

Perhaps pubescent Douglas watched this video too many times. If someone has the AI computer skills to 'age' this video 25 years and starring the titular characters of this thread, maybe Douglas will have his own answer.

 

[Redmt]

May I have a picket to Titsburg please

 

[Gr8bawana]

Yup , I still am amazed at how many young guys have no idea about menopause . My best friend years ago had it bad , she dried up and shrank to a size that sex was not possible for her . It hit her hard as far as her self worth , she went off the deep end , but she was crazy to begin with , but in a good way . Then she just got crazy crazy , it was sad to watch .
It hits all women different , some never recover , I've seen it ruin marriages , sad to see .

 

[Redmt]

If it’s off the table then walk and just get a fat girl your own age to play with.

Fat girls are like Mopeds. Their fun to ride until your friends find out.

 

[Redmt]

View attachment 283101

OH HELL YES! Someone find my walker.

 

[Hilljackoutlaw]

tits Magee

My dad used that one a lot. Still in use today.

 

[Hem]

Amongst a small group of my pals years ago there were ladies known as Skeletor (skinny), the Crypt Keeper (old), Bonesaw (braces), dumb Terri (dumb), Peter pants (wet her pants when drank too much), tits Magee, crazy eyes, and I’m sure others I’ve forgot.

We're these girls the extent of your high school?