My Plight

So my roommate asked me to go to the store to pick up some stuff for people that are coming over this weekend. She gave me her credit card to get the stuff. We could have gone later today, but she has a lot to do and I wanted to get it done for her. Seems like a harmless chore. So I go to the store, get the stuff and, of course, I am the only person in the last 38 years to have someone ask to see my license. Really? Come on. It was awful. (Maybe I am being a little dramatic, but hold on) There were two ladies working at the register I was at. I told them just to cancel and I would use my card. One of the ladies just kept shaking her head at me in disappointment...I felt like a seven year old whose mother just caught her playing instead of making her bed. I left the store.
See, my whole life has taught me to not be a rule breaker...actually, it has shown to not even be a rule bender or pusher. The only time I have ever sped, I got a ticket. The one time I got my parents to let me stay out as long as I wanted in high school, I had an encounter with the police (I wasn't actually doing anything, but apparently my friends and I looked "suspicious"). I have come to feel like I can't take any chances because the moment I do I get a slap on the wrist and someone shaking their head in disappointment at me. And I end up going home with knots in my stomach feeling awful about myself.
I think is what has happened to me in the past year. I muster up enough strength to venture out and take some big chances. Now I feel like I have come home with the whole world disappointed in me and my decisions. I feel like I took chances trying to love people and they all blew up in my face. And although I know that the situation is much more complex and that the Lord gave me wonderful things through all of it, I feel the same things I felt when I left the store earlier-embarrassed, angry, stupid and sad.
I guess what I am now trying to figure out is how do I move on and still take chances? It is too scary for me most of the time. I am always afraid of being hung out to dry. But I know that in order to love people the way that Jesus did, I will have to take chances. But is there ever a point when enough is enough?