That site has its own message board. The vast majority of OP’s are “a man/woman just did this to me. Why do all men/women do this?”
The vast majority of replies to those threads are “We’ve done this one to death! Please use topic search!”
The problem is that the line between boldness and obnoxiousness is a bit fuzzy, and varies between women. Being obnoxious to woman Y may be being unassertive to our 58 year old example. Men who aren’t obnoxious, but who cross the line anyway, may find themselves ratcheting down the assertiveness to minimize the nasty comments they get back. Judging from my daughter, the exact same line may be great from hunk Z and obnoxious from nerd X.
It’s all too complicated for me. I’m glad I’m married and out of the fray.
Hey, the fray ain’t half so bad until the casualties start piling up. 
Bolded a great point above–I think a lot of times when a particular word, phrase, attitude, etc… is ‘obnoxious’ or ‘bold’ it’s really shorthand for ‘how in the world did this person get the impression I’m interested’?
A man cannot, cannot, cannot neglect to be fluent in body language.
Assertive good; aggressive bad.
A woman’s four favorite animals:
A jaguar…in the driveway.
A mink…in the closet.
A tiger…in the bedroom
A jackass…to pay for it all
- embroidered on the baseball cap worn by a guy getting arrested for shoplifting cigarettes on COPS.
He was probably stealing them for his woman, just to keep her happy sniff.
Why aren’t men bolder with older women? Maybe they’re not that interested in her in the first place, preferring younger girls. Men can afford to be choosier; as noted, the supply/demand thing shifts because men die younger.
[Quoting Johnny L.A.]So she met this guy online. They exchanged phone numbers. They agreed to meet up sometime soon. He hasn’t called, and he didn’t respond to an email she sent him on the weekend. She did see he was online at the dating site (something about fish). Question for me: Should she call him?
I guess older men can afford to expect the woman to push the interaction along more. Again, supply/demand.
The spectre of multiple divorces past has probably left some of the men skittish. As posted above, the “young, dumb, full of cum” days disappear in later life. One or two painful and expensive divorces often suffices to sucker punch a guy directly into adulthood.
Overall, it sounds like she wants to be perceived as she was when she was 18. Why can’t a guy just come up and tell her she’s the hottest woman he’s ever seen? Because even if she once was, she isn’t any more.
Potentially NSFW:
http://
media.ebaumsworld.com/picture/
shutout81/HotChick.JPG
Enjoying your new, high-def TV, are you?
Really, that’s way too much data to try to fit onto one hat.
Maybe the thief had hydrocephalus.
Or Towers meant to say “t-shirt”.
In my observation men aren’t particularly bold around young women, either. I can’t think of the last time I saw a guy agressively come on to anyone, in or out of a bar.
I think men are plenty assertive.
I swear to God, it really was all on his hat. I’ll take a screencap of it in a little bit and post it up if you want to see it.
I believe you. I’m just a bit surprised, for two reasons:
A) I’ve never seen a message that long on a baseball cap.
B) Considering how small the letters must have been, I’ve never had a television that would render something like that legible. Unless, maybe, they did a zoom-in and freeze-frame on the cap in question.
This is not directed at you, Argent, but clearly the world at large needs a refresher on Robot Arm’s Rule #1 for Pithy Sayings on Garments. KEEP IT SHORT. I need to be able to read it while walking past you on the street. Anything longer than that is just going to annoy me that I did not receive the full wit and wisdom that you are attempting to inflict on the world. Save the manifestos for your Facebook page.
On the issue of whether she should call him or not, he may just be giving the line some play as I continue the fishing analogy. In dating too, just because you’ve hooked them doesn’t mean they’re caught and landed.
The guy probably has several lines out and gets these luke-warm we should meet or something where they’ll be coyly unsure and evaluating him with crossed arms. Now, instead he gets them slightly interested and backs off. Now they are trying for him and he’s the one evaluating the ladies who are trying to land him. It’s a delicate dance in fishing and dating.