Does my foot kick back that far?

Ever had a situation present itself and you walked past it and later, gave yourself a swift kick in the pants for walking past it?

A few weeks ago, I went to visit my BFF April up in Ocala. I don't see her very often, she gets busy with the kids, I get busy with friends and stuff, so we only see each other a couple times a year.
We'd hung out and played video games with the kids and made waffles and just chilled mostly. It was a really nice time. Usually when I go, she puts me to work painting rooms in her house - which is cool since I've run out of rooms to paint in my house.

Anyway, I was on my way back to Orlando to meet up with another friend and I made a pit stop for something to drink.
Sitting outside the jiffy store, there was a girl (looked to be mid20s) holding a sign that simply said, "Going South". There was a dog sitting next to her. It wasn't apparent if the dog (which was quite large) was hers or not. After running inside to grab a water, I came back out and was about 5 seconds away from sayin', "Hey, I'm going to Orlando, wanna hop in?"

But then that cynical/non-trusting switch turned on and, instead, this is what went through my head:

"If that's her dog, it won't fit in my backseat."
"What if she's a crack head that's gonna slit my throat and steal my car?"
"What if she's running some scam and has a midget partner in that bag she's got with her."
"I'm going to South Orlando....not exactly the greatest spot for someone to say 'You can drop me off here.'"
"That bag is totally big enough to hide a midget."
"I really don't feel like chatting it up for the next 1.5 hrs."
"What if she's really annoying?"
"What if she's in really big trouble with the law - could I be considered an accomplice if I give her a ride?"

While all of that was running through my head, I quietly walked past her, smiled when we met eyes, and hopped in my car.

So, since then, I've been wondering, "What if all of that crap running through my head was just total and utter crap? That girl might've ended up having a really great story about why she ended up sitting in front of a jiffy store, and I could've been that one nice person that helped her out with a quick ride to Orlando."

This cynical head garbage has also popped up again since that time.

Matthew and I went to Chili's one night with my mom. We ate dinner at the bar and there was a woman sitting next to us, enjoying her dinner and a glass of wine or two. She had what looked to me like a home made cast on her right arm. It was a layer of cotton (like she yanked it out of a throw pillow) wrapped with an ace bandage. I noticed she wasn't favoring this arm at all. Not holding it to her side or showing any sign of limited use. When she got her tab, her card declined, and she had no other form of payment. The manager came out and spoke to her and she said she'd be back to pay for it the next day. My mom leaned over and asked me if I wanted to be nice and split this woman's bill. I'd had the same thought a few seconds before mom mentioned it and then watched as she downed her remaining wine, wrote down her contact info and then grabbed her large bag - all using her right arm that was swaddled up with her SusieHomeMakerPillow cast. And who the hell carries only one form of payment - IN A BIG ASS BAG WITH A BIG ASS WALLET IN IT??
So, I said, "I was going to but I think she came in here for a free meal."
Then Matthew watched her walk out to the parking lot, hop into her Escalade, and drive off.
Matthew and I proceeded to point out all the flags we'd observed to my mother who said, "Jeez, you guys are more cynical than I am."

When did this happen?
When did I stop trusting the general population?
Do I watch too much news? No, that can't be it....I watch a total of about 20mins of it a day. That's not near enough to be fear mongered.
Is it just something that happens as you get older?

I do wish I could go back and give that jiffy store girl a ride south.
I don't really care about going back to Chili's and splitting that woman's bill 50/50 with my mom. C'mon, that lady was driving an ESCALADE.

When was the last time you missed an opportunity to help someone out? Or better yet, tell me about an interaction with a stranger that left you warm and fuzzy inside?