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Should I go for it or am I setting myself up for a fall?

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Question - (27 November 2010) 1 Answers - (Newest, 28 November 2010)
A male United Kingdom age 30-35, anonymous writes:

This girl's a housemate of two friends. Let's call her M. Of course, I like M. Last Tuesday was her birthday, and two friends of hers (a boy and a girl) came up to visit her. The next day she tried to hide the fact that she had a guy around for what seemed to be fear of judgement (she had previously told myself and all my friends that she does not in fact have a boyfriend). One of my friends was talking to M about all this and he told me that there's no point in going after her. At this point, I thought that she was taken and my gut feeling was wrong.

The following day, feeling pretty down about it all, I proceeded to try and block M out of my head and focus on the future. That evening and yesterday, my mate (the one who talked to her before) retracted his statement and told me that M liked the guy we thought was her boyfriend (not sure if she still does) but both him and his ex are now close again (his ex is presumably the other girl that came up to visit M). He in fact asked M, "Do you want me to stop looking for other girls?" to which she replied, "No, do what you want."

During this conversation, my name happened to come up in conversation too, and she said that I was confident, but at the same time, shy, like her. Does the fact that she mentioned me in this way to one of my best friends prove anything at all?

Whenever I'm around her, I'm always the focus of her attention - I'm the only one out of my group she really talks to, I suppose I can hold a fairly decent conversation, but the point I'm trying to make is that we're both pretty shy. We banter all the time and she takes the piss out of me but she doesn't to anyone else that she knows... and I can make her laugh.

So, I'm now in a dilemma. I'm confused and to be honest with you, already pretty drained. She's a shy person and so am I, but now I think I'm standing at the brink of a precipice and now I need to make a leap of faith. The problem is, do I have enough to go by to make this leap worth it? I have her MSN but I'm far too scared to add her. I don't want to risk the awkwardness that would come of asking her out or getting to know her further.

What do you make of all this? Is there hope for me, or am I setting myself up for a fall? I need an outsider's opinion!

View related questions: best friend, his ex, msn, shy

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A female reader, Bella555 United States +, writes (28 November 2010):

Of course you're setting yourself up for a fall, but the risk is certainly worth it, don't you think? She could say yes, after all, and you'd embark on the fragile but fun beginnings of a brand new relationship, and all the wonder and euphoria that go along with it. Some of life's best experiences and feelings may await you in that potential situation, but only if you're willing to take that almighty risk and work and hope for the best.

Considering you're both shy people, I recommend you try hanging out as friends away from your group. This may offer you a means of taking that risk without the embarrassment of an audience, or the piss they may take if you play the fool in front of them. She's your friend already, you seem to have a decent rapport, so what does she like to do? What's she into? Where do your interests intersect? Plan a fun (but light) time out with her, something event-based or easy, like a drink or coffee. Even if she says no, she may surprise you once she learns you're interested and turn the tables, asking you to go out or simply do something together without the pressure of a date. Friends make excellent partners in relationships, as you can build on your extant bonds and really strengthen your partnership.

As a side note, just ask her if you can add her to Messenger, that's all. Don't make that one bigger than it is. If she gave you her MSN ID on her own, instead of you getting it from a third party, I wouldn't think twice about putting her on your friends' list.

Good luck--hope it works out!

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