Felonious Attitude

Something happened on Saturday on my trip with D to Toronto for her company Christmas party that really made me think about myself and my responses to certain situations, and made me wonder whether other people have the same sort of reaction.
I woke up around my regular time on Saturday (10 AM) to D prodding me awake, but doing so with offers of coffee, so I forgave her. I also knew that I had to be up so we could travel to Toronto, and that she'd been awake since early morning at some cookie faire doing work. I didn't really have a leg to stand on if I had chosen to whine about waking up, so I woke with as much grace and forebearance as I could manage (I rolled out of bed and whined at D for about a minute, incomprehensibly).
Luckily, she knows this is just a defense mechanism and continued to prod me until my brain actually engaged.
After coffee I became as lucid as I ever am, and realized that in my sleepy stupor I had already dressed myself. I checked for unwanted undergarments attached to my clothing, found none, and D and I were off to Milton.
I'd like to take a moment to make a comment about Milton. It's flat. It's VERY flat. And because it's flat, it's windy. It also has the world's highest concentration of townhouses. These features combine to make it the most inhospitable city I have ever visited. It's like finding one's self on the surface of the moon, without the moon's aesthetic appeal.
We had to visit Milton in order to take the GO bus into Toronto. It is a good, safe place to park until early in the morning, and most importantly a free place to park.
We got to Milton later than intended, however. We were about 10 minutes late for the bus we had wanted to take, and had to wait about 3 quarters of an hour for the next bus. When we arrived at the GO station we parked the car and headed over to the terminal, hoping to buy our tickets. As we approached, we spied three men standing at the doors to the terminal. Now, I'm suspicious by nature, so when we got close enough to be hailed and the first thing out of one of the men's mouths was, "Hey, you guys got a smoke I can buy?" I was instantly on guard.
The three men were in fact two boys, and one man. I'd say the boys were probably 15 and 17, and the man was mid 30's. The man was in the process of taking off his belt and throwing it in the garbage as we approached, which was odd to say the least. All three were also clutching identical clear plastic bags, each with a slip of legal sized paper inside and containing what I assumed at the time to be shopping.
We quickly departed when we found that the terminal was closed (I can understand why no one would want to work on a Saturday in Milton, so I wasn't too miffed.) and went to find coffee.
After returning with coffee for me and apple juice for D, we parked and chatted, and I noted that the three men had vanished from the terminal. We were chatting for several minutes when I suddenly spied them loping across the parking lot back towards the terminal again. They had probably been to a nearby convenience store or some such while D and I got drinks.
We decided to brave the wind, the cold, and the desolate parking lot and go wait for the bus, so we did. We quickly froze as we crossed the lot and entered the bus shelter. I say "shelter" in the loosest sense possible, because for all its solid construction it may as well have been a hastily assembled pile of screen doors. Wind resistance was certainly not its strong suit. In the shelter awaited the three men, who were minding their own business, just waiting for the bus. The oldest of them even commented to D on the cold, and she replied in kind, courteously. I don't think she had any suspicions yet as to the nature of the three men, but some had definitely been brewing in the back of my mind.
I noticed that on the ground inside the shelter lay one of the plastic bags the men had been clutching, now empty. The piece of paper was in fact a label. It stated:
"(indecipherable) Police Services." at the top. And further down, "Property Bag, .50 c"
These three people had just been released either from prison, or from a jail cell, having completed their sentence or been parolled or even having met bail. Whatever the case may be, my first assumption was that these men were criminals.
Why did I jump to this conclusion? These men may have been drunk and tossed in the drunk tank overnight. Maybe they had been caught sharing a joint or two, which I don't consider a crime. Maybe it was a case of mistaken identity. I had no idea. All I know was that I suddenly wished I had a police officer nearby to watch these men and make sure they attempted nothing illegal.
I question my reaction because it says a lot about my sense of tolerance that I leapt to immediate distrust of these strangers just because of circumstantial evidence. I was terrified for D, afraid that we would be mugged and beaten, robbed of our funds and left for dead. Why? I had no evidence to justify this reaction, since these men had essentially left us alone, not even giving us suspicious glances.
Should we be immediately suspicious of strangers? Is it the safest thing to do? Or should we fight those impulses and approach even the most intimidating stranger with a sort of cautious optimism?
I know the decision I came to. Keep them in front of me and don't let them see where I put my money.
And make sure D doesn't wave her wallet around like a tiny flag in front of potential criminals.