On a night out, I spotted someone I liked the look of. He's known to one of my friends, through the tedious link that her boyfriend's mum is good friends with his mum. I didn't get the chance to speak to him that night, but to my surprise my friend informed me the next day that he was interested in me. How did she know? From his mother!
I'm not shy myself and I'm confident approaching people. Usually. Think the involvement of a gaggle of mothers has thrown me out this time! Thing is, although he's started to appear at all my regular haunts, (golf course, swimming pool etc) he never even acknowledges I'm there by so much as a glance. (In spite of my friend nodding knowingly and pointing out his new hairdo..) How can I approach him, or should I, when I'm not really sure he wants me to?
I'm shy myself, but not quite like that. If a guy is shy to the point of not even giving you a glance, then he'd better be OK with whatever approach the girl takes - or he's going to be very lonely. Does your friend know enough about him to give you a topic that might break the ice? Does she know what any of his interests are? Well I guess you have something to go on already. Golf and swimming. He either likes both, or he's going there to be near you. Seems like you can't lose no matter what you say - unless it turns out that the mom misread the situation. Then you will know the real story at least.
My boyfriend is shy and was the same way. You just have to take the chance and just like what rafael151 said use those to break the ice or if you not sure about that why not find a reason to walk by him and just give him a flirty smile and say hey and see if he will feels a little more comfortable with talking to you if not then try to talk to him. Maybe he just isn't sure if you like him or even notice him. if you do the hole smile thing maybe he will get the courage to talk to you.
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Describe your ideal first date; Where do you go? What do you wear? How does the date end?
A day at the beach or pool , then a casual place for dinner, then for a walk on the beach to look at the stars. Then the hot tub back at my place. I wear a little summer dress and you wear ripped jeans and a nice shirt. Falling asleep talking and watching a movie.
Afterwards..what will your date know about you?
Anything he wants to. Except what I look like without my clothes on. We'll save that for the second date.