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Too shy..too scared of rejection! So how can I make a move on him?

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Question - (29 May 2007) 2 Answers - (Newest, 29 May 2007)
A female United States age 30-35, anonymous writes:

i am quite a shy person... when guys i am attracted to talk to me i usually freeze up and make a total and utter fool of myself. But on the same hand, i have never had any problem taking to "guy friends"... it's odd. Maybe it's just the idea of talking to a guy i don't know, who i am attracted to, that makes me goof up. Anyways, to my question...

about 4 years ago, when i started high school, i saw this guy... being typical i developed a crush on him. most of the time when he saw me he would smile, and i would smile back, but nothing more. because he was older than me the next year he was done school, and off to college, 2 provinces away, and i did not see him for about 3 years... until last summer. I never actually knew who he was before then, but during those three years i found out who he was, and that i knew his parents and had been to his house on 2 or 3 occasions with my parents (or course, he was not there). my mum had met him though, and she kept telling me what a cute, sweet young guy he was... hint hint on her part, but i never clicked in that it was the same guy until a little while later.

the crush had subsided over the years, as most do, but with my new discoveries it came back stronger than before. he is now so close, but still so far away in a sense.

there have been other times when i have seen him, and he always makes a point of smiling at me, and i get the idea he is shy.

i would like to make a move, to show him i am also interested, but we have never talked before due to my lack of confidence and fear of buttering up. i am not 100% sure he is interested, so i am afraid of rejection, but i need to get this crush out of my system and find out if it is something, or not.

What can i do?... what can i do to build confidence in myself? what are some good conversation starters? how do i approach him without seeming weird? how do i find out if he is interested (are there signs?)? should i use my knowledge of his parents (and his of mine) to get to know him?

pretty much anything you can tell me would help, cause i really do need all the help i can get.

thanks in advance, chloe

View related questions: confidence, crush, move on, shy

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A female reader, Pretty and proud United Kingdom +, writes (29 May 2007):

Pretty and proud agony auntOk lets focus on you, you are shy, now try to think why? If it is because you have been rejected before then think to yourself thats his loss,this guy is also shy so if you dont make a move you will never know, plus somebody else could make a move before you, when you see him next just talk about something you think you might both be interested in and just get to know eachother,using the knowledge of yours and his parents is a great idea to get to know him because it will make him feel as if he knows you already. Now back to focusing on you, build up your self confidence by being a bit louder and maybe dressing differently than usual or putting on make up that you would never usually wear, after feeling uncomfortable wearing things you usually wouldnt, you will then feel more comfortable when you get your usual clothes and make up back on, this will make you feel more comfortable in yourself, think to yourself, "i am beautiful, i am capable of getting that guy" and then just charm him. If you want to know anything else then just send me a message xXx

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A male reader, DV1 United States +, writes (29 May 2007):

DV1 agony auntSince he's a guy, you really don't have much to get stressed about. Guys are really easy to approach. If he's smiling at you, then you can tell right off the bat that he would listen when you introduced yourself. Go up and say that you've seen him around, and ask him about himself. It should be smooth sailing after that.

Dv1

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