How to get to know a man who is mysterious. Sneaky questions to ask him?

This man I'm dating seems to be a bit guarded. I want him to believe he can trust me and I think I'm doing a good job. How can I get him to disclose some information about himself? Last night he admitted to having low self esteem. That's the most deep detail I've gotten out of him. I've tried to compliment and build his confidence a little with small steps. We've only known each other for 3 weeks.


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Most Helpful Girl

  • By taking Baby steps with your newbie newfound Who-----We've only each other for 3 weeks------Little by little with nursing and nurturing your date mate relationship, he may feel the urge to start talking and telling you more about himself.
    It's a sure sign and a good one at that that he Gave to you a 'Most deep detail' part about himself as it is already... however, I am quite sure you already may have surmised it for yourself.
    And with getting to know him better, you may 'Surmise' some more in store as time goes on and realize he is not what you may want.
    For now, until you make any decisions concerning Anything, be patient, try and keep the lines of conversation open and who knows... he may start to feel comfy enough to open up about a lot of things you----Didn't know.
    If you feel he is work pursuing, then go with his slow flow and feel him out as to how long it may take and if you both have a chemistry to Make what it Takes.
    Good luck. xx

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What Guys Said 2

  • What type of information are you wanting to know? Introverted, former shy guy getting over self esteem issues here.

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  • Hold onto his wrist under the guise of an affectionate gesture, monitor for heart-rate fluctuations during his responses. Ask easy to answer questions and then good deeper for cross reference.

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What Girls Said 1

  • Okay so I'm one of the shyest people ever so I completely understand where he's coming from. With me, no matter how much I like a person, I'm only able to be completely myself after a lot of hanging out. I slowly become less shy each time of hanging out with someone & if we last long enough to become best friends, then I'm my crazy, adventurous, silly self. That's once I am thoroughly convinced the person genuinely likes & cares about me. Otherwise, my mind subconsciously makes me the way I am & I can't help it. Trust me, I've tried. If you really like him, be a patient friend & he'll open up.

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