I have a friend that I've been friends with for over 10 years. My two oldest teenage boys are the same ages as her two teenage boys. The two youngest went to preschool together, that's how far we go back. Well, her oldest is 18, and he's always had social issues. He was diagnosed with a very mild form of asperger's, but is extremely functional. He drives, has a full-time job, has friends, but can sometimes be irritating due to his lesser ability to read social cues. He calls and texts all of us frequently, sometimes late into the night. My kids have always tried to be nice to him, but most of the time it's a bit of a strain for them, as it's out of obligation since I'm such good friends with his mom. Don't get me wrong, I've known this kid for so many years, I can be looked upon as kind of a second mom to him. But that doesn't minimize how difficult he can be to be around. Through the years, he has done a number of things while over at my home that his mom has overlooked. When the kids were much younger, my two boys had a go-cart that they would drive around our driveway. He got into it and was a bit too rough with the pedals and permanently broke it. I did get a sorry from his mom, but that was it. My boys were so disappointed. There have been so many more things since then...rough-housing in my upstairs hallway, he threw himself and put a big hole in my wall. More recent things have been, he lit the tiki torches I have attached to my deck and went to pour regular tiki torch fuel into the lamps that required gel fuel only. Luckily one of my kids came in and told me what he was doing before he lit it. I came out and told him to stop because it was the wrong fuel, and he immediately started to pour the fuel back into the container right over my freshly stained deck. He stopped when I told him to. He was adjusting my new garden hose sprayer and turned the adjustment ring too hard and broke it. We had a loose screw on our deck, and the board was up a little too high; I was afraid someone was going to trip on it, so my son got the the electric screwdriver to try add another screw to tighten the board down. He took the screw from my son and positioned it so far to the edge of the board, the board cracked, and now I have a hole there. He was playing around with my water inlet valve in my pool, changed the direction of the water flow, luckily didn't break that. He had his iPad plugged into our boombox on our pool deck so he could play his mp3 music through the stereo. He wasn't paying attention to how far he had the iPad from the boombox and pulled the boombox face first right onto the deck, badly denting both speakers. His mom was there for this one, they both said sorry...but didn't say a word to me acknowledging how damaged the stereo was. The stereo incident happened last week, and I'm to the point where I'm nervous about the next time he comes over. Any advice on what I could do here?? Thanks.