how early into the courtship phase do you start asking uncomfortable or personal questions and probe for the dealbreakers

Jalether

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My wife and I discussed a lot of these things on our first date. Keep in mind, we were both 36. I’ve always asked important questions early, because I don’t like wasting time, or money.
This is the way.

This is why I also advocate smashing as soon as possible (3rd or 4th date max) to find out if her hygiene game is on point

Imagine wasting months just getting to know each other only to find out her coochie smells like the serengeti
 
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This is the way.

This is why I also advocate smashing as soon as possible (3rd or 4th date max) to find out if her hygiene game is on point

Imagine wasting months just getting to know each other only to find out her coochie smells like the serengeti
I smashed 4th date, but it was a month in, which didn’t make me feel she was too easy. Plus, she invited me over for dinner for 3rd date.
 

Hoshi_Toshi

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After I think the relationship might go somewhere.

A lot of people out here aren’t fit to be dating in their current state. Once you peel their layers back like shrek you start to see the horrible upbringing and need for therapy.

So now I give them about 6 good dates then start asking questions.

Also watch how people talk about their parents.
 

I.Go

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I have certain criteria before I even go out with a women. She has to have a college degree, Job, No kids, under 35, single of course.

Luckily it's a large dating pool of good single educated women. The past is the past and as long as she ain't into sex work or been SA'd

cause I personally deal with that level of trauma. But I focus more on having a good time then drilling with hard questions.

Normally Date #1 I ask the basic questions. Date #2 I ask more question about their past relationships why they broke up.
 

Serious

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Asap why waste time.

I’ll go a step further. I screen a woman 4-7 weeks before even taking them out.

During that time, I’m asking all type of questions. If we not a match then obviously the convo won’t lead anywhere and communication will naturally fall off.
 
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