I stopped by a Money Box location to cash a sizable check when I needed the money and my bank was closed. I noticed ragged-looking couple who were in there when the teller was counting out my cash following me to my car without conducting any business inside. I was a bit edgy since I knew that they knew I had over $1000 on me at the time, and everything from their looks to their actions just seemed wrong. I put my hand on my pocket carry, turned around, looked the guy straight in the eye and asked him if I could help him with something. That seemed to catch them off guard, and the guy stammered some story about how his life sucked and they had no money, and he just needs to get his wife and baby (no baby in sight, btw) to his brother's place in San Antonio and if I could spare some change for gas. I declined, but offered to give him the number for a church group who would gladly feed them, talk to them about Jesus, and buy him a bus pass. He reluctantly took out an iPhone 4G and took down the number.
I got in my car, locked it immediately, and left.I'm guessing it was more likely a "scam this guy for money" thing than a possible robbery, but everything about them set off alarms in my head.