Met someone. How to open/loosen up and ask her out?

I met her at my friends bday party. I had trouble opening up and making conversation. I'm afraid she thought I was boring or not interested. I recently went through a painful rejection with someone else where there were some very strong feelings involved. Throughout most of my life I've dealt with bipolar, anxiety, ocd, adhd and possible PTSD. I've suffered traumatic and painful experiences. I become overstimulated easily. I'm fairly shy/introverted and insecure although I'm more confident than I used to be. My emotions are fairly repressed to the point it's hard to make an emotional connection. In result I've poor communication due to poor/lack of social interaction and any interpersonal relationships/friendships have been challenging. I can't help the way I am. I've shut my emotions off, isolated myself because of my painful past. I fight not only my inner demons but also struggle everyday to stay strong for those that matter and improve my health and mindset.

I've lived life fairly secluded, not many friends or much social interaction. I've been single over half my life. I've become accustomed to solitude, independence and being self-sufficient. Anything else invokes discomfort, awkwardness..

This new interest and I share similar experiences. Still, it's hard for me to open up and have things flow smoothly. It's like my mind goes blank and I literally can't think of what to say. In result my responses are half-assed, awkward so that's raised a few eyebrows or mixed responses on occasion. Is there any proper way I can get the ball rolling with conversation and convey this to her? How can I flirt when I'm emotionally closed off and guarded? How do I flirt period? How would I go about asking her out for a drink or date?

Updates:
15d My friend was trying to hook us up. Should I convey all this to my new interest or talk with my friend about it? I imagine they might wonder why I'm not very chatty and have barely said much. We are friends on FB however I haven't initiated any conversation w/ her yet.

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What Girls Said 1

  • You can try talking to your friend about it in order to help you out/give you some tips. Maybe you shouldn't go out with her alone so soon. Maybe you should hang out in a group setting once or twice before attempting to ask her out.

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What Guys Said 1

  • First you need to introduce yourself and shake hands. it might not be to flirtatious but starting that way gives you some ground to begin flirting. You can say i like that name, or that name is unique I've never heard it before then proceed to saying "(Her name) what do you like to do/etc?" After that if all goes well you should be able to get her number or just go out on a date.

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    • 15d

      We were already out for drinks for my friend's bday. My friend was actually trying to hook us up. I wasn't quite ready to be thrown out there yet. I felt incredibly discomforted and awkward. The loud music made me feel overstimulated and making conversation was difficult. It didn't go so well, however I tried my best to not overthink and avoid any negative thoughts and self-degradation like I would've done in my past.

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