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How can I chat him up without sounding too obvious?

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Question - (10 November 2007) 2 Answers - (Newest, 20 November 2007)
A female United Kingdom age 36-40, *hiteshadow writes:

I'm 20 and I work in a huge store in the stockroom which near enough sells everything. I'm really tall and look about 25. I really fancy an older guy who is 30-35. I thought the crush would go away but it hasn't and I have never fancied anyone in work before so I don't know how I can approach it.

I can't even look him in the eye anymore and he always makes jokes and does silly things which makes me smile and like him more. He has a cheeky way about him which often makes me shy and go silly. I do get a slight impression about the way he acts that he is either flirting with me or just trying to be a really funny friend. It is really hard to have a conversation with him more than one line because the place is so big and everyone is always running around and there's not much chance we would bump into each other alone cos there are so many people who work there.

I want to get to know him or chat him up but I don't know what I can say without sounding too obvious. He could even have a wife at home for all I know. Even getting the moment to ask him something is rare. So when I do which I have a few times so far, I don't know what to say, my mind goes blank and I start to stare at him all silly.

I would be so embarrassed asking him something too forward as I would be scared of rejection. The only thing I could think of is the xmas night out but then again everyone from work would be there too so maybe not such a good idea. Help meee please. Any reply is good I guess :)

View related questions: crush, flirt, shy

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A female reader, whiteshadow United Kingdom +, writes (20 November 2007):

whiteshadow is verified as being by the original poster of the question

whiteshadow agony auntI never went for it only cos its in work. I dont want to risk my job or reputation i have. I will just have my little daydream in work =) lol

anyways thanks so much for your great advice

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A male reader, anonymous, writes (10 November 2007):

Well, I think the first thing to do is try to find out if he is married or has a girlfriend. Maybe ask him if he will be with family over the holidays. If he does not, then I think you are free to ask him out. If you can't get a free moment at work, try to meet him somewhere outside of work. Like if you need help with something at your home, like something needs fixing, or you need help hanging something or something else you don't know how to do, ask him if he could come over to your place to help you with it.

Most men would love to be asked out by a woman, especially someone much younger, prettier and sexier than women their age. So I would encourage you to go for it. Don't worry about the rejection. A woman will generally be more successful when asking a man out than a man will when he asks women out. Find out if he is available first, and then go from there. Post back if you have other questions and I will try to answer them.

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