When it comes to work I always like to be as careful as possible. For over a year now I've been talking to a woman on and off at work. I only see her occasionally, about once a month or so. The convos, though very enjoyable and nice, have only been friendly. They have also always been sort of cool and casual in nature. Nothing too deep and a lot of laughs/sarcasm thrown in. We've talked about our families, our hobbies, work, etc. However recently I decided to finally turn it up a small notch... She is about to get a promotion in a few months which has been a big topic between us for the last 7-8 months and I (semi jokingly) told her that we have to make a deal to get a celebratory drink (pointed to new bar that opened next to the office) when it happens. She casually laughed and said she definitely, though we moved right on to another topic and if I were a betting man I'd say she didn't take my comment very seriously. The rest of the convo went very well with me for the first time giving her a few subtle compliments.

The goal now is to try and finally start getting a bit closer and feel her out more, so that going out for a drink could feel cool and casual as opposed to something that might make her feel pressure which is the last thing I want her to feel at work. To me it's all about making sure she never ever feels uncomfortable and to keep this very cool and casual vibe I've been pulling off with her for the last year plus. I figured there's no better way to try and do this by exchanging numbers. Problem is we do not work closely at all and have never ever had a reason to give each other our numbers. I'm trying to think of a perfect way to pull this off so it comes off completely nonchalant and indirect. To be clear, I do not and can't see myself simply asking her for it. Anyone who'd like to chime in with their two cents, much appreciated.