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:

1. Intention, everyone has to know it is a date.
2. A date typically has some hint of a potential romantic and or sexual interest, even if it's subtle, not stated overtly, or vague. Having said that, it's better to be bold and clear. When I first started dating I used to go in slow for the kiss when the vibes were right. I never misread the vibes too badly, but it's 2024, so now I always get verbal consent before I even kiss someone. I was honestly surprised at how often "I would like to kiss you," or "would you like to kiss me" gets a yes. If you get a no, most people are thankful to have been asked and that somewhat counteracts any awkwardness from being shut down.