"You'll Never Feel READY to Walk Over"

Next Monday you'll feel more confident. After the gym you'll feel more confident. After one more drink you'll feel more confident. After you get a better haircut, a better jacket, a better job.

You've been "getting ready" for two years.

She's standing ten feet away right now. She'll be gone in four minutes. No amount of preparation will manufacture the courage that only comes from moving your feet.

Walk over. Stumble through the first sentence. Let it be clumsy. Let it be imperfect. You will feel more alive in those ten seconds than you have all month.

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So I Met This Older Woman...

L

labyrinth

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I met this woman while walking my dog about a month ago. We stop and talk for a few minutes just about every night. It's always small talk and I've never really flirted too much. The thing is she is probably in her early forties, probably 41 or 42 if I had to guess, and I am 29. She seems to be mature and probably would not respond well to me being overly flirtatious, negs, or any other tactics I might try in a bar, club, or somewhere. Anyway, she seems really cool and I am interested in her, but it's hard to really gauge if there is any level of interest on her part. There's probably a good chance that she would consider me too young, as well as too immature (if she really got to know me).

Any tips, advice, on what I should do. This is a unique situation for me and I am not sure how I should go about approaching her.
 

"The Coffee Shop Girl You Never Spoke To"

You've replayed it a hundred times. She stood three feet away, scrolling her phone. You had an opening. You composed the perfect line — after she was gone.

For all you know, she's married now. To some guy who said something. Anything.

Openers are cheap. Almost any sentence works when it's delivered within three seconds. The expensive part is the standing there, drafting and deleting, while the window quietly closes.

The "22 Rules" stripped out my hesitation. What to open with, how to keep it alive, and the one habit that costs guys more women than anything else: waiting for perfect.

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K

ketostix

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You should probe her with some flirting and suggestive questioning. You need to act fast before the window of opportunity passes and you're just in the friend's zone. Just go for it.
 
D

Dongfu

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older women love younger guys - just be straight- no pick-up tricks
 

"How I Made Sure No Woman Ever Friend-Zoned Me Again"

She calls you when her car breaks down. When she needs help moving. When some guy she's actually dating treats her badly.

You're the listener. The reliable one. The guy who would treat her so much better, if she'd just open her eyes.

She won't. You trained her to see you as the low-effort option — the friend who requires zero risk and zero investment. Every favor dug the hole deeper.

The "22 Rules" break the pattern. You'll stop auditioning for a role she already cast and become the man she chases instead. It starts with Rule 1.

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F

Francisco d'Anconia

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window said:
go for it...
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I don't know, even though it should be an easy pickup (at least to gauge her interest level) all he seems to have are "tactics" that lack any substance. We could be leading an ego-lamb to slaughter.
 
L

labyrinth

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Well, I'm not sure this will be an easy pickup. I think it's actually going to be much different than anyone else I tried to get. She will either be flattered by an attempt by me, or think I'm an idiot. It seems like older women who don't really get out and party or go to bars are vastly different and wouldn't respond to a typical approach. My only experience is basically the clubs and bars, and occasionally college back in those days, and I can't imagine that approach working very well in this case. I have never been with anyone more than a year older than me so this is brand new.
 
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22 Rules for Massive Success With Women
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