A
male
age
41-50,
anonymous
writes:Hi all, I was hoping for some advice on something that's been on my mind for quite a while now - I'll try and keep it as short as possible :)There's a girl at work who seems really nice and I would love to ask her out on a date/drink/whatever.But the problem is me. I wouldn't say I'm the most attractive person - though, my own opinion, not -that- bad :) But I can be quite on the shy side and lack friends outside of work, and as a result I've had no luck when it comes to women - which doesn't do much for my confidence!Although we don't work in the same office we have been to different events (nights out/sports) involving a handful of people (so she knows me!). I have spoken to her, but I'm more likely to do this over work email (and not flirty type, just usually related to whatever event is coming up with a bit of humour thrown in sometimes, etc)Now, to me, it makes sense not to out of blue ask her out or anything like that. But another idea I thought of is to ask one of her work colleagues (female) that she's close to, to see if maybe she thinks I stand a chance with her? Obviously that could backfire, but there's one person in particular I have spoken to and she seems nice and I would hope that wouldn't happen!I know one obvious suggestion would be to talk to her more, but this is extremely difficult at the times I see her face to face - especially with me being a bit on the shy side, etc.Hopefully that made some sort of sense! I'd really appreciate some help on this one!Thanks
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female
reader, anonymous, writes (2 October 2008): Hey there,
Okay, so of course getting to know her on a more personal level is the obvious suggestion. But i can also understand how that may be difficult for you. A good way to start would be asking her questions here and there, in a casual way. For instance mention that your interested in trying a new restaraunt, ask her for suggestions. Get my drift?
That way you get to know her without giving the impression that your interested in her. Go from there, keep it simple and subtle, no pressure. If speaking one on one with her makes you uneasy, try it with a group of mutual friends/coworkers. And if you wish to ask one of her coworkers about her, also keep it subtle, do not in anyway give the impression you are interested, i say this from experience. The whole office knew (that i liked him) before the end of the day! haha.
Just remember that you cant lose what you dont have! A moment of humilation or a lifetime of what if's? Best of luck!
A
male
reader, Ed1337 +, writes (1 October 2008):
 Like you said the obvious suggestion is to talk to her more and get to know her better before you ask her out, you might find out that she isn't even your type.
I'm fairly shy myself, so I know how hard it can be. Just remember that nothing bad will happen to you if you start talking to her, she won't tell you to get lost or insult you, just talk to her as if she is your friend and not somebody you fancy.
You said you email her regarding work events, if your worried about getting to know her face to face, then why not email her instead? Ask her how her weekend was, or what she is doing this weekend, things like that.
Good luck
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