Got any good ideas?

Question

My friends and I like to go out regularly and do something a little... embarrassing. For instance, we like to walk up to random people and just say "Hey, long time no see!" and see how long we can keep the convo running, or walk up to girls and go "You suck. You know why?" and try to come up with a reason on the spot. Just silly, harmless stuff like that. We're going out again tonight and maybe tomorrow night. Anybody got any ideas for stuff we could try?

Answer 1

I disagree that it is harmless. To me, your second example sounds like intimidation. Why don't you choose non-offensive routines like...
1. asking where lives, it's somewhere nearby ... you must know him, everybody knows , he's about , maybe you've seen him out and about he's the one that drives a etc.;
2. one of you detaches from the rest, then the group ask passers-by if they've seen person matching the other's description, it's very important - you could be searching for a lost friend (he could be deaf or feeble-minded), or trying to find someone who has taken your house keys by mistake (etc.), when the passer-by assures you they haven't seen him, the group continues down the street, shortly the other friend walks towards the passerby .... see what happens.