…rather than how was your weekend, say something like “What was the best part of your weekend? Tell me in great detail.” This will get a chuckle and will get them talking more than just “how was your weekend?” I always try to avoid the boring “Question traps” as I call them. The kind of this like “How are you?” “Good and you?” “Oh good.” “That’s good”…
I like funny, situational start ups, depending on where you are!
Grocery store (after you’ve made eye contact) - “Hmm. You look healthy, what are you eating and I’ll just copy you!” Or “These froot loops aren’t for me, in case you’re wondering. They’re for my grand…sister’s…ok they’re mine”
Book store - “Ahhh nothing like coming to the book store and pretending like I know what I’m doing here!” Or "Excuse me, can you help me find the “How to start a conversation with someone who appears much smarter than myself” section?
I always try to find the humor in any situation. It’s non-threatening and puts people in a much more agreeable and open frame of mind. Don’t force it