re: In your younger days, how shy or bold were you about asking a girl out?

I had no game whatsoever. Asking a stranger or someone I knew only a short time out on a date was not something I ever even attempted. I could get laid in a bar often enough to make going to bars attractive but that is different than dating by a mile. What I did have was a lot of friends and acquaintances who had sisters and female friends who I had an "in" with. Never had any abnormal aversion to asking them out and most times wound up having a nice enough time. I caught my limit just a few months after my 21st birthday though so I was never really faced with being out of school and on my own and trying to date....its far easier when you are still in school and still running with your friends than it is when they start getting married and spending less and less time socializing.

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Not so much shy as clueless. I had a class in college with a girl who always smiled and talked to me every day. It wasn't until much later that I realized she spent the whole semester throwing mad hints I never picked up on.

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God I wish I could go back to college for just one semester knowing what I know now about the game.

I had TONS of female friends that I met in classes. My guy friends would always marvel at that when we would go out and I was always seeing girls that I knew. I was really good at making friends and I was awful at knowing when I could/should explore the next step.

Junior year, a girl and I were friends in a sociology class and we always talked before and after class and exchanged phone numbers in case one of us missed class or something. One day I missed class and called her that night to ask what I missed and I was gonna also maybe suggest that we do something together outside of school....and a dude answered the phone (this was before cell phones). Turned out she was living with her boyfriend that she never mentioned. No big deal....but I think that kinda spooked me a little and I never recovered from it while I was still in college.

Looking back, there were definitely some opportunities that I wish I had tried to pursue. But oh well.

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My mother raised me to be polite. That got me friend-zoned. Took me a long time to realize girls like the assholes better than the polite guy. So I started being an a-hole who just didn't care. Worked like a charm and made it a lot easier to be bold.
Contrary to everything I was told about girls wanting a nice guy, they were far more intrigued by the guy who was a prick and showed a lot more interest in me when I was one.

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I don't know about the prick part but I picked up pretty quickly that nice, but indifferent was a pretty good combo, they become a bit intrigued and challenged when you don't immediately start drooling and fawning all over them

I usually came up with pick up line that went with the moment...

I met a girl who had spinach on her teeth while eating spinach dip. Told her she had a beautiful smile, but that spinach on your teeth is totally ruining it... Got her number.

Told a girl, I don't know what you'll think of this comment, but your arse looks great in those jeans... He face lit up, she had on a new pair and she thought her arse looked too big in them, and she was just telling her friends... Worked out...

I was never scared or worried about talking to women, I figured if you hit on ten, and you hook up with three, that's like hitting 300 in the majors...

and sometimes it wasn't about the pick up, but the thrill of the hunt...

Did I get shot down, sure, but I didn't give a shite... All about the confidence... Married for over twenty years now, wife is 14 years younger, if we divorced, I wouldn't know what to do now... shite has changed so much...

I asked em all out. In the early 90s, It’s a numbers game. Summers in Monroe were a playground of girls looking for a fun day. Rarely got the “I’ve got a boyfriend”. I’d just tell em I didn’t think he would mind. I’d get numbers on a napkin and write down descriptions on it to know who to call the next week.

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As soon as you don't give a frick, they start giving a frick about you.

I don't know why, but it's an absolute fact

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It is human psychology to want what we can't have. Now of course I didn't figure that shite out until later

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Willie Stroker

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We’ve been married 30+ years.

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Ok, I'll share one story.

Had this ongoing rapport with the girl who worked the register at the grocery store. Just chit-chat, joking around, I never used any lines or hit on her.

She was cute as hell, and in the words of Alex Stein 99, a big booty Latina. Her hair was jet black and shiny, blunt cut, she took deluxe care of herself. She was a reminder of film actress Violet Myers (NSFW). Guys were hitting on her all the time, I'd finish checking out at the register and I'd hear the next guy up trying to chat her up.

One night I'm at the register and absent-mindedly put paper towels that were on the conveyor belt into my cart before she scanned them. She says, 'I see what you did there.' I just smiled because I didn't even realize what I had done or what she was talking about. She was letting me steal .50 cents or a dollar's worth of paper towels.

Actually saw a similar scenario on a TV show where another character had to explain to the guy that the cashier was giving the guy free stuff because she liked him. I don't know, looking back, I think I knew at the time that I probably could have asked her out, but life circumstances at the time weren't the best.

I don't even care about the missed connection, I'm just more embarrassed that she thought I was trying to steal stuff. I hope she put in the charges for those things manually, but I didn't check my receipt at the time and it's all in the past now.

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In your younger days,

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I never was the one that did any asking.