the cool thing is that either way you chose to do it, there will always be chances to try it the other way. first time i did shrooms i was with my friends, but i was the only one shrooming. since then i have done shrooms both with other people and by myself, multiple times. each experience has its own high points. you just have to experience both.
I've done shrooms by myself and with a friend. THey are completly different experiences and i recommend trying both however i do enjoy doing them with a close friend much more. The first time i tried psychedelics i did acid by myself i tripped pretty hard and some how i ventured out of my house and got lost in the woods it was intense and a scary but great experience. If you are doing it alone and this is your first experience with psychedelics i recommend a smaller dose but its completly up to you. Just make sure you are in a safe place.