I need some advice!

Good day,I hope this week is treating everyone well—only a few more days until the Easter long-weekend is upon us! I had a question and any advice, comments or suggestions are much appreciated.First off, I am a young professional (25) and I work for a fairly large company in my home town and a I live in a small city that's about 110,000 people; therefore, the city doesn't have the largest scene, but it is getting better! As you probably know resources are limited, and I have put myself on POF, and Grindr—also attended some of the pride events in summer (I am trying here). I am your classic extrovert and meeting people comes naturally; however, I am extremely shy when it comes to putting myself out there when I happen to like someone, or have a crush—I have had some unpleasant experiences, to say the least. It also does not help that I don't really have any gay or lesbian friends—minus my one dear friend who is a lesbian and quite a bit older than me. My main group of friends consist of straight girls and guys. On another note, I don't declare myself masc or fem, but I do find people have some trouble reading my sexuality. I find some people clue in instantly and some people have no idea.Nonetheless, it's been hard to meet someone and I ask the question "will this ever happen?!". After a bad experience in 2010 I stopped trying to look for a relationship and just focused on school and my career. Last year I started chatting with a guy on Grindr and it eventually after a few months turned into a coffee meet and things really went well and I was surprised and was taking things slow but we went on an official date before he had to go outta town to visit family and it went great—he tried to arrange another date before he left but our schedules didn't work. But, after that he dropped off the face of the earth and I wondered "What the fuck". Turns out when he was out of town his sister set him up with a guy and they hit it off fabulously and well here I am today—I do want to apologize for this ever so long thread!MY QUESTION: I have a crush on a guy that works at the organization I am at and I'm not sure how to pursue this. I'm fairly certain he's gay, but I am not 100%. We do not work in the same department, and my role and his do not even cross paths. We do randomly talk and chat and we're both friendly and he seems like he's interested, but I could be reading into it.I am not sure how to approach this, but I wanna take life by the horns! I just need to ensure I'm respectful and be mindful he is a coworker.Me: I have always had doubts on myself and I am very critical on myself. I am a chubby guy, but I have been told I hold it well. I always get compliments from older people 45+ that I am incredibly handsome, and I could make any "girl" happy-typically older people always think I'm straight. But I rarely get compliments from people my age—I mean if I wanted to I could get ass, but I want connection. I do know I need to work on my self-esteem and I need to make some changes—I have been working out and trying my best to be healthier—baby steps!Thank you! I appreciate all your comments, suggestions and feedback.Take care,