Search Results: girls who flirt with shy guys

So there is this guy at my job who is 30 (I am 23). I have had a crush on him for the better part of 6 years. I was in a long term relationship until a few months ago, and after we broke up my interest was renewed in job guy. He's a pretty shy guy who had a girlfriend a long time ago but who hurt him really bad somehow, and has only gone on a couple of dates since then.

Before, I'll even admit, I was way too young for him, and I had not had any previous relationship experience. Now, I have had a long term relationship under my belt as well as graduated from college, so I feel way more mature. We went to the same college (not at the same time) and are both in a health profession (I am in grad school and he has a full time job). About a month ago (with the coaching of my boss), I texted job guy to see if he would be interested in hanging out. I have attached a screenshot.

I only see him once a week at work, so I've been trying to talk and flirt with him those days. One week we talked about his nephew and how I got my first patient in my field. The next week he was sick and called out and the following week when I came in he was like, "if anyone every offers to give you ____, say NO. Very painful."

I was off this past week, so I had people talk about me while I wasn't there (oh, X is my favorite manager, her hair is so beautiful, I wish she were here, etc) to see if he would react. I snapchatted this one girl and she said when she got it she was like, "OMG, X snapped" and he turned around, and when she asked him if he wanted to be in a group snapchat back, he said he doesn't look good in pics.

So, since it's been a month since I asked him to hang out, I'm just wondering if it would be wise just to text him and say hey or not. Please help!