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I was a late bloomer and I still feel like my brief brush with religion in my late teens and early twenties crippled my social skills for over a decade. Having said that, I managed to have a few awkward dates here and there and fewer still became relationships. Something they don't tell you is that 80-90% of dates are awkward and terrible, but for many people including myself, when it clicks, it clicks.
I knew a woman at work once. I always stay very professional at work but I am friendly and nice to people. One day we were doing some bullshit paperwork and had a really good conversation and at some point when we were smiling and laughing I felt the vibes. We got a beer with friends after work. A few weeks later she got fired for some stupid shit but we stayed friends and dated for a month or two after. In this instance dating was primarily fun and adventurous. Getting to known each other etc. Bonus points because she had a cool roommate and her ex who came by for the kiddo once in a while was a cool too.
Another women I dated was already a longtime friend of mine. She went away to college and I saw her rarely for years. When she moved back, I invited her to hang out and we hit it off. We had a lot of fun and I felt the attraction, so I asked her out on a date. Because we had such a strong friendship beforehand, dating her felt like hanging out with my best friend, but more romantic.
For me, the thing that changes it from friend hangout to a date is: