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How do I start talking about this with him?

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Question - (7 April 2012) 3 Answers - (Newest, 9 April 2012)
A female United States age 36-40, anonymous writes:

Hi, So I have a bit of a situation and it'll probably help me explain it more if I share a little bit of a timeline.

There is this guy "Jay" and we've been friends since we were 12 years old (I'm 23 now). We went to middle school and high school together and still see each other often because we share the same friends. Well, all through senior year of high school is when I started to realize I really really liked him, but I never thought very highly of myself and thought he was way out of my league so I never pursued anything.

As I've said before he and I..and all of our close friends still hang out all the time. We share one VERY VERY close friend named "Dave". Well Dave informed me that this past December he and Jay had a conversation were dave finally asked jay if he had feelings for me and jay said "yes, very strong feelings" and that he'd always had feelings for me.

Well I didn't see Jay after that until the beginning of march. We spent the weekend together at our close friends house. all of us together, but jay and I were practically joined at the hip. I've just spent the last few weeks thinking about him and this past thursday and friday night I stayed at his place and it was fun and we have the BEST friendship in the world. I love him to death and I know that my feelings for him are still there and probably stronger.

He is very sweet to me and obviously values our friendship, but I can tell he still has feelings for me. He is affectionate like a guy is to a girl when they are dating or in a relationship...and there's so much more, but it's not all that necessary to write about.

What I need help with is how to go about talking about being more than friends or at least getting it out there in the open that we do like each other. Both of us can be awkward when it comes to putting ourselves out there and neither one of us can be the first to say something, this is the only time we ever get shy or quiet around each other (when we start to get serious about one another. I want to try and be the person to get the ball rolling, I just don't know how. Help, please????

View related questions: best friend, shy

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A female reader, Trinklett Canada +, writes (9 April 2012):

Trinklett agony auntAsk him out to a movie and try to say something to him. Its not an easy task but he could be waiting for you to make a move. Since he's told Dave how he feels about you he's also looking for an opportunity to get it out. If you're too shy to say anything, after the date, send him a text - one line. I like you a lot. Reply.

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A male reader, Great or Good South Africa +, writes (7 April 2012):

Great or Good agony auntBeing shy I don't think it will ever helps you than hurting you, I think it will hurt you even more if you find that he is going out with someone because you took for ever to sort this matter out.

This is what I mean, as a man it can be possible that he values your friendship a lot and that can makes it hard to start such things of being morethan friend because women gets to be too emotional sometimes, and unpredictable then he might see that you looks interested while is the opposite you just value him as a best friend.

Ask him out for tea or coffee then when you you guy are out tell him how you feel about him,

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A male reader, anonymous, writes (7 April 2012):

Gosh just text him saying i like like you. You already know he likes you in that way

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