During my semester at Texas State, I had a particular incident with a hitchhiker that spanned 10-12 hours and involved a fair amount of weed, an iPad 2, more sketchy situations than I can reasonably count, and a $250 watch.
So at about midnight one night, I left my house to go get some food from this 24 hour burger restaurant (cause you know, Texas). As I get through the drive thru, this obese black man walks up to my car and starts tapping on the window. I was gridlocked at the time, but I didn't seriously think he was going to do anything right there in front of a restaurant and as close to a highway as we happened to be, so I rolled my window down to see what was up. He basically said, in so many words, that his car was broken down, and he needed a ride to a town about ~25 miles away to pick up the part he needed at a mechanic and that, if I helped him out, he would give me an iPad 2.
Now, keep in mind two things before you judge me too easily; one, I was incredibly bored that night. I needed something to do, and this stupid incident seemed just stupid enough to be entertaining. Two, I hadn't met a person in that town who I didn't trust, and I had met quite a few people already, so I didn't think too much of his story beyond just bad luck on his end.
So I agree, and let this dude in my car. We head out after getting food and make our way to Austin, and all the while he's asking me questions about who I am and what I do, and I'm just giving every evasive answer I can (Example: "So what, do you live around here?" "Not really, I sort of go from place to place, depending on who I know and where they are. I'm never anywhere for very long"). Then he starts asking if I smoke weed, which I responded "Hell yeah." So he asks if I want some, and we go to this shady ex-military dude's house who, in regular circumstances, would never really want to come in contact with. So we get a bit of weed from him, then head out, but just as he lights up, the situation I'm in starts setting in and I figure out the best way of getting myself out safe is to stay level-headed and pay attention to what was going on.
So the night goes on, and within about an hour, I figure out this car-part thing was just bullshit. We're at this point just driving around kind of aimlessly, and every opportunity I have to drop this dude off somewhere, he winds up with something of mine (most commonly, my phone, which was used for calling the people inside to not freak them out, which arguably would've been the lesser of two evils). Eventually, I remind him of the iPad, and we go through this random ass neighborhood for about an hour just trying to find one house in particular. After a while, he runs out of weed, so we give up, drive back to the shady dealer, and get rejected there, but across the street an equally sketchy motherfucker happens to sell too.
For this entire instance, we are basically driving back and forth between dealer's homes and this one neighborhood, and the longer I'm in this situation, the more conscious I am of what I'm doing and how to get out of it. At one point, we stopped at an abandoned pool to meet a couple girls that would supposedly have weed, and I hid my debit card in my shoe, he had my phone, and if anything happened, I was planning on throwing my keys down the pool drain. Needless to say, there were quite a few sketchy stops where I was making these kind of plans until I realized this dude wasn't gonna jack me unless he absolutely had to. So I made it my best interest that he not have to.
Around 8 AM, I realize this dude is way too high to reason adequately, and that he isn't going to try anything in his current mental/physical state, so I start pushing him to get out of my car, and he eventually breaks down, saying that he has to make one more stop, and then he'll go, and as collateral, he gives me this $250 watch. So we get to his stop, and of course he finds another excuse to keep going, so we start driving on the highway, and at this point, I'm looking for a cop just so I can start speeding to get his attention.
At this point (9:45 - 10:00 AM), he sees the car that we spent hours looking for in that neighborhood, and we start following it into downtown Austin (state capital of Texas). Somehow, and I honestly don't know how I pulled this off, but I convinced this dude to get out of my car and knock on their window in the middle of the road. He does, and I quickly check to make sure I have everything I left with; phone, wallet, keys, debit card, and anything else I valued. I had everything, and so I lock my doors and look up to see him on his way back. He starts knocking on the window asking to be let in, and I just yell "No! I'm done man! Forget it!" The light turns green, and I peel off down the road, and the last I saw of him was his fat ass jogging after my car, holding a drink cup in the air.
I managed to get back to my dorm around 11:00 AM, which is ironic considering that was around the time I had initially left, and I passed this group of kids who had been sitting out on the patio outside my dorm hall at the time I left. I just kind of waved casually, walked in like nothing had happened, flipped shit to a few friends I knew, then got on mumble and flipped even more shit, then went to bed. Needless to say, I skipped school that day. I ended that day having lost around 12 hours of my life and ~$200 (spent mostly on weed, initially for the two of us, later on just to get him stoned enough to do something stupid), but gaining a $250 watch and this gem of a story to tell.
TL;DR version
>left my dorm at midnight to get food
>at drive thru, random guy walks up and needs a ride somewhere
>offers iPad 2 in exchange for ride
>gets into several sketchy situations
>10 hours later, still dealing with stoner mooch
>dumbass gives me his watch
>winds up getting left in the streets of some town
>finally made it home, still needed food
So yeah. Moral of the story; don't trust hitchhikers. You've been warned.