Alright, so about 3 months or so ago I was out at a bar with a friend. We were partying and having a good time in VIP. There was this HB8 there who looked depressed. I waited for the right time and approached and started conversation. Convo was mediocre. I could tell she was sad about something so I tried to uplift he spirits and make her smile. I did so. Well after a bit of conversation I decided to make my exit from our conversation on normal terms. Did so. I was pretty confident I would see her again because she is friends with one of my friends. She ended up being one of the first people to leave and when she left I began talking to some of her girlfriends and wanted to get in good with them. Told them I liked their friend etc and asked what was wrong. They told me she had just been dumped by her boyfriend. Again, I was happy I exited the convo earlier to avoid quick rebound status. So, I showed them I was interested in her but let the night go on. Well about a week after this I asked my friend about her. He told me to add her on Facebook and gave me her full name. I did so. She took about 2 or 3 weeks to accept even though I could see from SOME public profile view that she had some activity. So, I knew she was making me wait on purpose.
Eventually she accepts and a couple days later I message her. She says it's good to hear from me again and tells me that she's newly single and how hard it was for her to get out of the last relationship because it was long term and they lived together etc. Well, her spirits seems to be much higher and better than that previous night. After a couple a days messaging her I send her a message saying "We should hang out sometime. Do something fun". She didn't read it or respond for a couple a days. I'm pretty sure she saw it in a header without reading it on purpose because I've done this to people before. So, I saw her post something about having pneumonia and trying to recover. I send her another message checking to see if she was feeling ok. About a day or two later she responds but not to the hanging out, but to let me know she's better.
So, she posted a status this Saturday asking if anyone knows any bars looking for bartenders. I know a ton of bartenders so I told her I'd talk to one and I got her an interview. She thanked me multiple times saying she was greatly appreciative. I want to see if I can get her to agree to go out with me but don't want to come off desperate. ADVICE???