I really like one of my friends--we've known each other for 4 months and I've liked him since I've met him basically and he's so perfect and he dated my friend but only for like a week she knows i like him she doesn't really mind.
I really like him but i don't know how to tell him. i thought i should wait for him to tell me but i kind of want to ask him out. but every time i go to tell him i back out and to tell him is easier said than done. I thought maybe i could tell him over the internet because that where i feel most comfortable because we aren't face to face but i think that's kind of tacky. Any Advice?

Dear Seeker,

The fact that you've known each other for four months and have been friends is in your favor. The fact that your friend is supportive is also a plus. It seems like you are ready to ask and just need a method. I agree with you that the internet is a bit tacky, however there is nothing wrong with a phone call, voicemail or text message. The key is to be specific. Rather than saying, "Do you want to go out with me?", make a specific suggestion. For example, "Would you want to get together on Friday night to go to the basketball game?" That way, if he says no, it shouldn't be embarrassing to either of you and the friendship won't "get weird".

If he says yes, just keep up the same strategy on a regular (but not too frequent) basis. If he says no, but seems like he has a valid reason--consider giving him one more chance. If he says no twice in a row, I would assume he just wants to "stay friends".