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Should I ask her out or wait a while?

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Question - (5 July 2011) 1 Answers - (Newest, 5 July 2011)
A male Canada age 30-35, anonymous writes:

So here's my situation:

I've been single for about 6 months now, the problem is, I've never gone on a "blind date" before because for the last 5 years I've only been in relationships. I'm kind of a shy person and it's hard for me to talk to a woman because I never know what to start with/say.

There's this girl I've had my eye on for a few weeks now, she's around my age and she just started working in the same office as me, I see her every day at the office but I rarely say anything because I'm so shy. I think she's beautiful and I want to ask her out for a coffee or something.

The only thing I'm worried about is that she says no and then I'd feel kinda awkward around her for the rest of the summer. Should I ask her soon or wait for a while?

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A female reader, aunt honesty Ireland +, writes (5 July 2011):

aunt honesty agony auntI think you should wait a while. You say she is beautiful which is a great start. But I think you should try and get to know her a bit better first before you ask her out. Start off by smiling and saying hello to her when you see her and then move on to making small talk just ask how she is, is she liking the job ect. Just ask her questions about herself and try and get to know her. Yes you are shy I completely understand that. But just keep it to a few simple questions. It really is not that difficult if you gather the confidence to do it.

After you have spoke to her a few times and got to know her a bit better well then ask her out and see how it goes then. If she says no well yes you will be disappointed but at least you know you will have tried your best and you can just carry on being friendly with her. Good luck.

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