Armed robbery, multiple times.
First time I was in 4th grade so mid 90s. I had gone out to get a slice of pizza, candy and basketball cards about two blocks from my apartment on the Upper West Side. It was rainy out and I think maybe spring break so not a lot of people around. A very haggard homeless guy comes up to me with a boxcutter, shows it to me and asks, "do you know what this is?" I did and got really scared. He then told me to give me all the money I had (about $7). I was so scared I offered to give him the basketball cards and told him they might be worth something. He ignored this and told me "Don't tell anyone or I will come back for you." I was terrified and ran home crying. Mom took me to the police station where we looked at some photo lineups and drove around in an undercover cop taxi to see if we could find him in the neighborhood. No such luck though.
I was in 7th grade on a rainy day with my friend at a Blockbuster 3 blocks from my apartment. It was a big store and there was hardly anyone there, and no one in our direct vicinity. Two older kids came up to us with razors and held them to our faces. Took our money, a discman and some headphones IIRC and then walked out. We didn't even bother reporting this one.
The next time I was in 8th grade. I was going to Lincoln Center area to visit a high school with another friend from my middle school. I had just sold a guitar to another friend that same day for like $100. As we went into the train station to go back uptown 4 or 5 older high school kids grabbed us and shoved our heads against the wall and said they'd bash our faces into the wall if we didn't give up our shit. Lost all the money and a North Face jacket and backpack. His mom insisted we go to the cops even though I didn't want to bother. We looked at photo lineups and drove around again in an undercover car but to no avail (obviously).
Last time was only an attempt. I was in New Orleans, where I have a lot of family, for Mardi Gras. We were going to a party with my cousin near the Garden District/Uptown area which is very nice, but if you go a few blocks the wrong way it gets a bit shady pretty quick. I was walking ahead with my friend and my cousin and our other friend were about half a block or a bit more behind. Two dudes came up to my friend and me and told us they had a gun (it seemed pretty clear they didn't since they didn't show shit, but its NOLA so we were pretty scared) and started trying to go through our pockets saying "yo lemme see that shit. Lemme hold that." Fortunately, my cousin and other friend (who was 6'3" ~325 Lbs) caught up with us and were like "what's goin on here." One of the robbers saw how big our friend was and booked it, but the other guys was too busy trying to get shit from our pockets to notice. All of a sudden he looked up, saw it was 4 on 1 with one of us being a man giant and booked it too. Nothing lost that time. My aunt was pretty pissed my cousin had us stumbling around wasted in that hood though.