1. When someone is in need.
I have often signaled drivers so that I can tell them a trunk or rear door is open. I have helped someone who's keys were in their trunk. Someone else I stopped was transporting a refrigerator and the freezer door was flapping open. They don't expect it; they're always surprised, not quite certain how to take it, but they are always grateful.when they find out why I was signaling them. And I offer the same type of assistance when I'm not driving.
The hardest time for people to do this is when the ‘need’ is embarrassing. I have told co-workers that their shirt is on inside-out or stained or whatever, but only when it is early enough in the day for it to be helpful. Of course, even late in the work day doesn’t mean they won’t be going shopping or meeting someone after work that an earlier observation would have saved them that ‘additional’ embarrassment.
2. When you can give a compliment.
My favorite story is of being at the Science Museum in an area where many people were waiting for something, I forget what. Two couples, obviously together, were talking about their lives, when one of the women said something along the lines of, 'Our daughter is so weird. She won't eat her ham sandwiches without grape jelly.' I just had to say something. 'Excuse me. I'm sorry to interrupt but I couldn't help overhearing, and I would like to say that I have just discovered the pleasure of fruit with my meats, and I would like to say that I think your daughter has very sophisticated tastes.' I don't remember if they said thank you; I just remember that they stood a lot taller.
3. When there's an opportunity to joke.
My good friend had this happen to him. He was showing off, talking with his Irish brogue, as he and a few others walked around a lake, when from behind him he heard a true Irish brogue, "That's not too bad." and a tip on how he could improve.
Good jokes are hard to come by, especially when they are not done at someone else's expense or by being crass. So, when I see an opportunity to say something that will get people laughing, I take it. The embarrassing part for friends who are with me is that I don't care who said the thing that will allow me to get the laugh. The nice thing is everyone appreciates a good laugh, so I'm able to get away with it. And I'm sure you will be, too, if it really is a good joke.
4. Anytime the Holy Spirit prompts you.
As a Christian, I am to follow the leading of the Holy Spirit in my life. Sometimes His instructions are subtle, sometimes not so subtle. So awhile back I determined that, since I embarrass myself enough on my own, if I feel the Holy Spirit prompting me to do something embarrassing, I will do it anyway. I am certain it will turn out far better than my own embarrassing of myself, and if God is leading I want to follow, even when it is into someone else's personal space.
I know a woman who was directed to write scriptures and a personal note on cards, then God told her the person who should get the card, and they were always strangers, and always they were blessed. My own experiences of this are currently limited to situations where I am with other Christians and we are praying; however, I know the day will come when God calls me to share His love with a stranger, and I can't wait for Him to show up in a powerful way, as He does in these situations.
Okay, okay, I have to end with a funny story that doesn't fit any of my categories. I took some friends to a little hole-in-the-wall ice cream shop. I was trying to explain how really big the servings were when one of the three bikers in front of us got his cone. So I tapped on the shoulder of this black-leather clad, burly dude, and said, "What size is the cone you're eating?" My friend was panicked, trying to stop me, but the guy turned around all excited, "It's a kiddie cone! Can you believe how big it is!"
I wish you all success in your endeavors to broaden your horizons and reach beyond your current sphere.