This one could be so complicated. Let me try and condense a quick back story.
I worked with company for 3 years. Liked Tasha who is a couple years older. We have simlar sarcastic, self deprecating sense of humor so go along well. For a long while she was a supervisor over me so I didn't make a move. When I got promoted alongside her last year I thought I had a shot but before I worked up the nerve, she got engaged. The engagement fizzled but before it did I took another job. When I learned she was single I asked her to lunch (something we'd never done before). We had fun but she talked about her fiancee leaving her. Complicated personal issues. I thought I might get an opportunity soon, but a few weeks later he sadly committed suicide. This understandably was devastating. She had her profile pic be the two of them for a long time. Changed it back about 2 weeks ago. We had dinner a month or so after his death, and lunch again last week. Also saw each other a week before that when I went back to old workplace for somebody's going away party (my first time back). She had to work at that time, and I knew she was sick, so I brought her
favorite snack. She thanked me like 7 times. IDK.
We had a great lunch, and she told me she's mostly over her big grief, though she finds herself feeling anxious, but we both admitted that's a constant state. I really am happy that we've become better friends now then we ever were in 3 years of being co-workers, but I don't want to get stuck there.
Would it be appropriate to say something on our next lunch like "I like that we've become friends who can hang out, but at some point, I would like to try for something more serious"?
Most Helpful Guy
That can really hit on the spot. Now's the time for that. You should really push that through.
Though it may entail a lot of risks, it's highly likely that she's going to accept you since you're always there for her when she needs somebody, treated her like a queen, and you're there as her closest friend.0