Good luck. Whatever you do, don’t express amazement over how hot she looks for her age.
And if you want to improve your chances of seeing her, propose an activity for the first date but also give her the option of suggest something else. Controlling behaviors don’t tend to go over well with the 40 and over crowd.
It is. Maybe there are a few others, but for the most part, it’s just you.
So, Shag, I hope you tell these women that you’re not looking for anything serious. At the very least, don’t let them think there might be a future. My guess is that the majority are looking for more than you are.
Me, for one. Shaggy writes like he’s hoarding commas for the Great Comma Famine of 2026.
It’s not entirely you thinking he’s getting bashed by people taking a goody two shoes position they wouldn’t take as much if someone was equally blunt but with the PC gods on his or her side. 
However he’s posted with a similar theme in other threads so I don’t know how to distinguish reactions to the previous times from reaction to this one. I’m not ‘offended’ by Shagnasty’s take on life though I do wonder what his perennial theme that ‘fewer marriages are happy than is advertised’ refers to or how he determines that. ‘Advertised’ by whom? And on a relative basis I really doubt the trend in society is for more people to pretend their marriages are good and suffer them in silence when they aren’t. It would seem those making any strong positive comment are simply self selected and no statistical conclusion can be drawn.
But back on people’s selective judgment of what’s unacceptable and even the dreaded mortal sin of ist/phobe, I can see that many don’t like the deeply embedded social reality that older men (especially assuming reasonably well off) have better prospects on average with younger women than older women do with younger or even same age men. Some exceptions don’t disprove that rule. That’s life in society so far as it’s evolved, AFAICS. Also it doesn’t typically generate a lot of support to talk about how you’re personally well off financially.
By starting this thread, the OP is marking himself as an older man who is having a hard time nabbing the nymphs of his dreams; we’re ribbing him for coming across as an entitled douche about it. So where are you getting this from?
If anything, Shagnasty looks like a cautionary tale for younger men who are confident that playing the field stays fun well until their 40’s and 50’s. Nope, eventually that shit gets tedious, lonely, and frustrating if you’re like most people. His posts are proof of that.
Didn’t you mention you grew up with a nanny?
Yes, but it was in the Deep South and didn’t cost much at all. We were generally middle class at least in values (my mother was a teacher at the time) but things went to hell when my parents got divorced when I was a young teen and we really were broke then. Lola worked mostly on barter. She was old with no family in the area. She stayed around the house, watched TV and occasionally ironed but she didn’t do a whole lot besides that when we were older. Her main role was to keep me and my brothers from doing something really dumb. We just loved her, took her on errands because she couldn’t drive, helped her to pay her bills and things like that. She first joined our family when I was 17 months old and still living in a trailer next to my grandparent’s house. That type of household help cost next to nothing back then in cash terms.
IIRC, she was only paid in room and board.
Look at it this way, Shag, you’re starting a new journey in life. Over the next decade or two you will slowly, almost imperceptibly, metamorphosize into a dirty old man, and all the grannies in the old-folks home will hide their 20-something year old visiting granddaughters from you.
That is a little about what I am worried about but I am not going to hit on anyone’s granddaughters as an old man (although I am certain I will still admire the pretty ones). I just realized that time is ticking and I can probably pull off a version of I want for now but it has a shelf life. Call it a minor version of a mid-life crisis but there are no combovers or sports cars involved.
I just want to get the best available while I can still get it. It will probably be different in ten or twenty years. I am already happy sitting in a rocking chair reading a book without listening to any complications or bullshit. Hopefully, it will be a smooth transition. I have seen lots of people do it incorrectly and I don’t want to do that. I am not sure though. I have never done this before.
nm
Maybe the “best available” could be someone you’re ignoring because of your overwhelming focus on physical attractiveness?
When your screen is drowning in spittle from self indulgent outrage, I accept it can be hard to read accurately. Perhaps wipe your screen and try again?
.
Great. So you can easily provide actual quotes from this thread to show this, right?
??? She’s talking about the 32 year old coworker who said if Shagnasty doesn’t date the woman, he (the coworker) will. If he said that if Shagnasty doesn’t date the woman, he’s totally gonna ask her out, that would sound better and, frankly, less entitled. Why the fuck is he assuming she’d be interested in him?
When trying not to comprehend, it’s hard to do so.
[my emphasis]
Think about it some more.
Why? I’m not going to waste my time. If you want to think you’re right and I’m wrong, fine by me. It’s not worth my energy to argue about it.
Yes, looking for support for your position would indeed be a waste of time. I’m glad you agree.
I have. Let’s break it down.
“I will have to see if I can go out with her.”
Shaggy is contemplating if he will decide to go out with her.
“The 32 year old officemmate says that, if I don’t, he will.”
But should he decide not to, his co-worker will step up and do it.
Nowhere in these two sentences is there any indication about what the woman in question wants.
Hey, I just had an idea. Maybe he and officemmate can switch places while having sex with her, and she won’t notice. I hope Shags has a good deodorant or his vagina smelling armpits might trip him up.