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age
41-50,
anonymous
writes: I really like this shy guy, but with his line of work, i am a 'client' so it makes the situation a lot harder to court him (thou i am not a direct client of his). I have written a question on here before and i get the impression that he does like me, but the challenge is that he is shy and the fact that his job does not make it easy for me to pursue things with him. I have striked up a convesation with him about what sport he likes which went well, but things have not been easy to follow it up. Recently ive been told that his colleague really likes him and have seen her giving me the dirtest of looks for whatever reason (i've done nothing to her, don't even know her), but this has stiked a cord in me to try and increase my chances of getting him to ask me out, but he is very shy, thou in his late thirties. To be fair his working enviriomnet doesn't allow much opportunities to chat about unrelated topics, just for hellos and goodbyes. My question is if he really likes me should i expect him to go out of his way to approach me, or do i need to go out of my way to ask him out, i really don't prefer to do the this as id like him to take charge on the situation, but he is far to good to miss out on.
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male
reader, TeardropsOnMyGuitar  +, writes (26 April 2013):
Quote:"Nobody is THAT shy at 30 something, he would be an unemployed loner if he was."While you may be right in *this* instance, it is just not that simple. My (now divorced) brother once said, "If someone is not married by 30, there's got to something wrong with them."I was single and getting closer to 30 at the time and it hurt to hear him say such a poorly thought out comment.When I was that painfully shy, I was also quite comfortable and not shy about discussing or arguing about politics or religion or how to go about doing things.I know how to hold a good job and what to say and not to say in the work place. I'm not a weirdo or ever was.Social connection is not my strong suit and I don't make polite social conversation easily. I need a venue or activity on which conversation can hinge. Cards, a board game or much better if I can help you accomplish something then I'll be more comfortable because there is a reason to be together and something to discuss. My religion at that time also gave me an acceptable discussion topic amongst that group of friends who also went to the same church.While *this* guy may not be interested, it is also possible that his is painfully shy(and still be a great or normal guy).
A
reader, anonymous, writes (25 April 2013): Nobody is THAT shy at 30 something, he would be an unemployed loner if he was If he was interested in you he would have made some sort of approach but he didn't even follow up on your chat about sport,which had broken the ice.You can ask him out,ask him if he is single, but I don't feel he will want to go or he would have asked you by now.The other girl may like him but I doubt she is giving you evils why would she, you don't have anything going on with this guy do you?
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A
male
reader, Glacier  +, writes (24 April 2013):
Women can be very jealous. It's very likely this colleague gives you dirty looks because you are competition for her.
This would be even more motivation for me to pursue him if I were in your shoes. (evil smiley).
I'd say that it's better to be a client of your love object than the other way around.
Anyway, I would go for it and ask him out. Let us know how it went.
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A
male
reader, TeardropsOnMyGuitar +, writes (24 April 2013):
I was painfully shy when I was younger. I had a huge crush on a girl that went to the church I used to attend in High School / early work years. We were 'friends'. For a while I lived a short distance away and we'd write to each other (nothing mushy - all friendly). We'd talk. The church atmosphere created an environment where I could be friends and see her a lot without having to date. Another guy friend used to ask me if I liked her and I'd always say 'no' out of embarrassment and fear. It would be easy to say that if I 'truly' liked her I would have overcome that but looking back, I really think there was something truly special that I stupidly missed out on. She went on to marry a dud.There was a period where she was making moderately subtle gestures and acts that would make it clear to a normal guy that she was interested. It wasn't enough to get me to act.When I started dating it was with girls that were below my league. My first girlfriend was a very very nice person but kind of butch and she turned out to be a lesbian in the process of coming out. I still think warmly of her as a friend and wonder what she is up to. I was however not that attracted to her sexually so she was 'safe'. All in all, I never asked out the ones that I really, truly liked. Ten years later I was friendly with someone who I liked similar to my first big crush. We had a connection and a venue to meet - evening classes. I never asked her out even though I could sense she would have like that. Another great opportunity missed.Had one of these two women taken the initiative and been open with me about liking me, I would have gone with it and picked up the ball and run with it.A little caution. It is one thing to get over the hump of shyness. It is another to be constantly pursuing. If you have to constantly pursue then he probably is not that into you.
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A
female
reader, eyeswideopen  +, writes (24 April 2013):
 I don't think you have any other choice but to ask him out. If he's so shy you might have to wait forever for him to get around to it. At least if you do it you'll know whether he really is interested.
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