I suggest tripping with a best friend that wont freak out if you are tweaking at something...I tripped on booms once with a best friend who also did a little but the other freind didnt and was acting all weird about us and being real gay to us. It sent me into a bad trip the whole night because he was al yelling at me because i made nonsence a couole times. Make sure your friend understands and tell him if you start talking nonsence to just deal with it and not tweak on you.
I have only done shrooms a few times and most of the times I have done them alone at some point I would feel lonely but nothing putting on the tv didn't take away right away, made me feel like there was people with me lol. And as for bad trips it seems like a few times my trips have started becoming not bad but a weird fealing of fear of anxiety came over me but that was all forgetten very shortly. I love tripping alone i say go for it.