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How do I ask out this shy guy at work?

Tagged as: Crushes, Dating<< Previous question   Next question >>
Question - (22 June 2013) 1 Answers - (Newest, 22 June 2013)
A age 41-50, anonymous writes:

I am very fond of an extremely shy guy at work. He has shown signs that he is interested, but unfortunately I only get to see him on a day to day basis in his department its been impossible to pursue him taking into account his shyness and the fact that I see him only in his department.

I feel that none of the flirting will develop whist at this workplace, but i do not know him outside that environment. Because he is shy he holds back especially in a public, but on the occasional one to one conversations he opens up to a degree, but because he is shy these one to one opportunities do not happen often and even still, because we are in this environment it is a risk to flirt.

How do i develop the flirting outside of this environment even though i don't know him, without stalking him? i've goggled and found his private email address, but not sure if i should use and can see that he is on facebook, But I know of him but not know him and our job roles don't interact and i don't want to come across as a freak. He is the shy type comes across as a 40 year old virgin type, Any suggestions?

View related questions: at work, facebook, flirt, shy, stalking, workplace

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A female reader, Euphoric29 Germany +, writes (22 June 2013):

Dear OP,

I'd try to find out if you share a common interest. Any interest that gets you an excuse to meet him outside the workplace.

For instance you can ask, did you have a nice weekend? what did you do? Did you also go to the... blabla.. event? And then find out what he does or did in his spare time. If he doesn't talk, open up a bit and tell about you first, maybe that will earn his trust.

Or you can find an excuse to talk about music, movies etc. and ask him to give you advice on what to watch next, buy next... maybe there's a chance he'll come along? For instance to a movie you both want to see but haven't yet?

Of course, it doesn't have to be the movies. Maybe he likes wine and so do you, and you could check out a wine tasting place. Or he likes a band that you like.

If you can't find any excuse, make up a reason to celebrate something with your coworkers and then invite him to come along. Or ask him for a small favour, like helping you carry something along the corridor and then bring him coffee in return so you develop a stronger bond.

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