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How to Talk to a Quiet Woman

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  • #1433

    Hey all,

    I’m a very outgoing person, which has often gotten me into trouble. I seem to attract very outgoing women. At a business conference this last week, I ran into an awesome woman (“Jane”). She was quirky and shy, but beautiful and sweet. It’s funny – I used to know her sister (“Dorothy”) who thought I was regularly flirting with her (“Dorothy”) because I used to say hello on the way to work (she was a shy one as well).

    Anyway, after some superficial conversation this last week at the conference, I feel that there is mutual interest and I’d like to message her online (we live a few hours apart). How do I message her without being too aggressive? What type of thing is appropriate to message a shy woman for the first time? Growing up, my sister was very shy and “forward” guys always worried her. I never really understood why – so, I’ve never actually gone out with a shy woman before.


    Just ask her how her day is going and see how she responds.
    Sprinkle in a little humor in the conversation. And end it with you’d like to stay in touch if that’s okay…
    Don’t ask her out at this point. Ultimately if (she) is attracted to you she’ll be flattered you reached out to her.

    After a few days go by touch base with her again and share with her something that’s going on with you.
    You might even (ask her for some advice or say you’d like her opinion) about a choice you need to make on something.
    Most people enjoy helping others because it takes them out of their own head and it feels good to be of help.
    This approach will also likely reduce her shyness as she won’t feel the need to be on guard for some pickup line.

    A week later reach out to her let her know you’re going to be in town and wanted to know if she’d like to (meet you) for lunch.
    By now you’ve been in touch multiple times, established some rapport, hopefully shared a couple of laughs. She’ll relax.

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