For over three years now i've liked and wanted to ask out a college at work, (we'll call her emma)

i know dating a workmate can lead to all sorts of unhappy endings but we don't actually 'work' together, but more for the same company. She works down the hall and I don't interact with her for work reasons, we really just meet at social drinks after work on fridays, (bar opens up in the main conference room so it is 'at' work).

Of late she's been making a concerted effort to join conversations that i'm involved in during these social drinks which suggests to me she may be interested. I think she might know I like her following drinks a few weeks ago when she was making continual eye contact.

She can come off a little cold, or closed off but I think this is shyness or maybe lack of confidence around some people.

I work quite closely with a friend of hers and was entertaining the idea of asking her what emma's situation is. I know she's single atm but thought this might be a better way of feeling out the ground without outright embarrissing both of us should I ask emma out thereby putting her on the spot. I know emma's friend would tell her I was asking after her which would get the ball rolling.

We also shop at the same supermarket, but I don't want to wait till I see her there again before asking her out. (figured this might be more comfortable for her rather than asking her out at work). I feel the window of opportunity is closing and any delays could mean I lose her to someone else.

Any suggestions for a guy who's a bit unsure and doesn't want to do the wrong thing?

Thanks.