"She Wants a Man, Not a Boy"

You asked her if she wanted to grab coffee. Then you asked if the time worked. Then you asked if the place was okay. Then you asked if she'd prefer tea.

Four questions. Four chances for her to say no. Four signals that you're terrified of making a decision.

Plan it. Pick the place. Pick the time. Tell her where to meet you. She'll either show up or she won't.

Either way, you look like a man instead of a scared little boy.

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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.
 

"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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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
 

"Stop Asking Your Friends What to Text Her"

Your buddy Dave has been single for three years and thinks "hey u up" is a valid strategy. Your other buddy Mike just got dumped and told you to "just be yourself."

You showed them her text. You asked them to decode the emoji. You drafted four responses and sent the screenshot to the group chat for a vote.

She's been waiting forty minutes.

Put the phone down. Stop crowdsourcing your love life. Type something that sounds like you. Hit send. Then go do literally anything else with your evening.

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F

Francisco d'Anconia

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window said:
go for it...
Click to expand...
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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