I've had both good and bad experiences through the years, but the vast majority of time I've enjoyed myself & had a good time. I'm comfortable playing with players of about any skill level; I'm good enough to be fine playing with great players, but I'm not at all bothered playing with guys who are lousy.
One of my funnier experiences was before a tournament I play in every year; at the time I was playing a lot & my handicap index bounced around just below or just above 1. A lot of my friends would go over the Friday before the weekend tournament to get in a practice round; I never did, but this time managed to slide out Friday morning. Called the clubhouse, talked to the pro (who'd become a friend) & told him I was headed over & asked if he could fine me someone to play with. I get there, talk to the pro, & he tells me my other three are out by the putting green. One of them, he says, is a high school kid who has some talent, and when possible he tries to pair the kid up with good players so he can get a better understanding of how good players work/think their way around the course.
First tee, the kid smokes a drive down the center; hits a long iron on the green for an eagle putt. Second hole is a par 3 & he hits a sweeeeeeet 6 iron that eats up the flag. As we're driving away from the tee, I comment to the guy I'm riding with that the kid has a really nice swing & looks like he can play. He responds, "Oh you don't know Matthew? He just finished his junior year in high school; he's won our club championship every year since he was in 8th grade. He's already committed to play for the university of florida - he's one of the best junior players in the country."
At the turn, the club pro sees me, smiles & says "so what do you think of Matthew's game?" I replied, I think I'll be watching him on TV some day.
It was Matt Every, who's won a few PGA events.