When most women want to build a relationship, they can usually sense the "correct" times to ask the most difficult questions. For example, questions about what you're looking for in a relationship. Or about your past.
And when they ask, they tend to ask in ways that make men comfortable. For example, they might talk about the time that they stopped seeing another eHarmony date, because he wasn't interested in a serious relationship. Which (if you are looking for a serious relationship) gives you an opportunity to empathize with her, and imply that you would have done the same thing. Or, give you an opportunity to say that you're looking for a casual relationship first, to see if things "build" later on.
They're good at this. I let them do it.
But... sometimes, they're not so good. And, sometimes, women will insist upon pushing past your point of comfort. For me, this usually comes down to asking intrusive questions about my former marriage during the first date (or before).
Sometimes, they react to subtle hints that we don't know each other well enough to understand such complicated histories. But, sometimes... they continue to insist.
So, why do some women do this? Because they're anxious. And usually, pretty damaged, themselves.
And the subject isn't what I'm uncomfortable talking about... it's what she's dying to talk about. It's about HER damage.
So, I turn it around. It usually doesn't take much. In my case, just saying, "I don't know... have you ever been divorced?", or, "I don't know... what happened in your", last marriage/broken engagement/with your last boyfriend, or whatever?"
They're usually dying to vent. Let them.
When they're talked out, step back a minute. Show them that you understand how hard it must have been for them.
And then... ask them how they feel about meeting other men after she's had such a blow.
Listen carefully. And decide if you're willing to continue seeing someone who has this kind of damage. (For me, the answer is almost always, "no".)
If you can't deal with it... tell her how you can't work with someone like her. And leave with head held high.
If you can deal with her issues... the agenda discussion is over. You've talked about the real problem.
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