Let go of pride and ego.
Find something the person may be very interested in, and get them talking about it.
"I can't help but notice that watch, can I ask you about it?" (Anybody asking about my watch is an instant friend. WHY WONT ANYBODY NOTICE MY WATCHES??)
"This might be weird but I need a new barber, where do you get your haircut?"
"Yooo where did you get that sweater?"
"You carrying golf clubs around the city? There a course I don't know about?"
"Is that a defcon sticker?"
Something unique about them. Find it, ask about it. Easy to practice. Just do the find it step to random people during your commute.