SUBREDDIT: r/dating_advice
TITLE: Advice for getting back into the dating world (with backstory) [20M]
POST: Hey /r/dating_advice, I was hoping to get some advice on what I can do to get back into dating (my goal is a real, exclusive relationship). As my title says, I'm a 20 year old male, and I think I've avoided some of the traps that many people seem to fall into. I'm not desperate, I very much have my own life (I'm multilingual, play an instrument, started my own company, etc.) and I am pretty comfortable around women. However, either nobody really has an interest in me, or I just don't know how to tell when they do (from what I've read the latter is more likely). I don't think I'm super attractive, but I don't think I'm horrible either (I can put up a picture if needed).

The main problem I have dating is that because I don't know when someone likes me, I never really take the risk of asking someone out, however there is a reason behind this. I've always been more interested in long term relationships than anything else, and when I was 16 I started dating the girl that I ended up dating until I was 19. She was great, and I learned a lot from the relationship, but sadly we found out when I was 17 that she had a terminal disease and so our relationship ended (quite obviously) with her passing. Once that happened, I moved cross country and started my company, but fell into a couple bouts of depression. Since that point I just didn't ever think about dating anyone. 

Recently though I have sought treatment for that depression and I have begun to want a relationship again, but I think in the time that I had sort of blocked dating out of my mind I lost all sense of romantic connection with people.

So my question is, do you guys have any advice for how I can maybe get that sense for who likes me back? or even, something I can do that would get me more comfortable asking people whose intentions I'm not sure about out? Any and all advice is appreciated!
TL;DR: 
After losing touch for a while, how can I get a feel for who is interested in me, and how can I get more comfortable asking women out?