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When is there a good time to say you like someone?

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Question - (23 August 2011) 1 Answers - (Newest, 23 August 2011)
A female United States age 30-35, anonymous writes:

When's the right time to tell someone you like them? Right now I'm in high school. I'll be starting my senior year in 2 weeks. So of course I'm in my puppy love phase where I get a crush on someone. The only difference is, that this is the first time I have some stuff in common with the boy I like and also, I've found him a bit easier to talk to than most boys I've liked. I like to think we've sort of became friends. Like he would sit next to me and sing me and my friend's names in songs just to be funny. He always comes to me for help on homework that involves artistic skills since he knows I love to draw. I actually drew him two pictures he requested, and he liked them a lot and went and showed them to people like he was proud of it, which I have to admit made me blush.

I've even borrowed his auto-biography on Keith Richards, and when he saw me reading it (he gave it to someone else to read and she gave it to me instead) he got all excited and was like "Do you like it? Isn't it awesome?" I feel like we get along really well. The only problem is, I don't think he likes me the way I like him. I want to be a bit better friends with him because like right now we're only scratching the surface of friendship. I just tend to get nervous. Sometimes when I talk to guys, I'll get nervous and won't be able to think of anything to say other than a simple one word answer. Otherwise I'll say something stupid.

Just once, I want to find someone who could be really good for me who might possibly like me back, but I don't know how to let him know I want to be better friends. For all I know, he might even already have a girlfriend! I just don't know what to do.

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A female reader, birdynumnums Canada +, writes (23 August 2011):

birdynumnums agony auntFrom what you said in your letter; I thought that he was into you. Of course; I haven;t the slightest notion if he has a girlfriend, that is up to you to find out. He is definitely send out signals that he likes you and barring the whole possibility of a non-existant gf thing - you should feel free to go for it!

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