That’s a great low risk drill to get started. It’s low risk because it works and you’re in an environment where respectful interruptions like that are acceptable. Good luck and if you get stuck, feel free to reach out.
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.
- Start conversion with something you notice about the other person, the event, the surroundings ("the color of your watch matches with your sweater - stylish!", "is this stuff boring or is it just me?", "you know why they put that thing over there?")
- Topics: Family, Occupation, Recreation, Dreams
- Repeat the last few words of the other person and look asking. The person will continue the subject s/he's talking about
- Connect and imagine the other guy. "I am a writer" - "A writer! I always wanted to be one but always stop after one page of writing. I imagine you must be very disciplined"
- Avoid RAPE (Religion, Abortion, Politics, Economics)
- You can always say nothing and just stay there. Often the other person picks up the conversation once you're past a few minutes.
- Try looking people into the eye while walking around, and force yourself to not look away. This is a nice training for looking strangers in to the eye in a cold approach. Once you got that, talking to strangers becomes much less intimidating.
- Eventually people will ask you what you do for work / or what you did today. Have something ready that sounds interesting.
As for tactics: just ask questions. Everybody likes to talk about themselves. Eventually, you'll get good at finding out what interesting things people have going on in their lives (most people have something).
- Board game/trivia group at your local bar
- Join Toastmasters
Secondly, be more interested in listening to the other person than in talking about yourself. Most people want to talk about themselves.