How old are you? My speech therapist in middle school had me go to the admin office, let them know what I was doing, and told them my favorite vacation trip. I did this to four different people. It was an exciting topic so I wouldn't be nervous to talk about it, and I'm meeting new people at the same time. Something I did as I got older was order food that was more tricky at restaurants, like adding substitutions, etc. ordering over the phone took me a while to get used to. Also, just strike up small conversations with cashiers, in line, small little practice session.