How did you guys get out of the friend zone?

Only had 2 girlfriends and I dated both around 18-20 when I was at college. First girlfriend was a girl I met in high school and I dated her for a month. I was a total idiot and didn't know how to be a good boyfriend. She got mad at me for some reason and broke up with me. Reminded me of a 16 year old girl that dissed me for wearing a Pokémon shirt and that was a major blow to my confidence. After that I didn't date much and just broke up with my last girlfriend 3 years ago. I feel like I'm in a rut and I want to get out the friend zone. I'm thinking of putting myself out there and be more risky. Any advice on some of my mistakes I made in the past or things I can do to improve?