What was the worst date you ever went on?

Met a guy at a bar, knew some people in common, but neither of us were good friends with the people we knew in common. It was enough for me to agree to a date. He asked me to meet him at a swank downtown restaurant. I was excited to be meeting there. He was insistent that I not order anything before he arrived. Strange, but okay... Then he shows up 45min late. He got “caught up”. Then he says he’ll order for me. He orders one meal, for us to share. Luckily I’m not picky, because how does he know what I will or won’t eat? The portions were quite small. We begin to talk and I find out he has 6 kids, with 5 different women. None live with him, but he does live with an ex. It just keeps getting better! We finish our tiny shared meal, then I find out he doesn’t have to pay, because he works security there and gets a free meal a week. Okay.

He asked if I’d like to go have a drink and call me crazy, but I wanted to see where this shit show is going! He knows just where to go, it’s a place that they have half naked girls dancing on the bar. I’m amused and wait for him to get me a drink. He never gets either of us a drink and I figure instead of getting myself one, I should stay alert on this ride! We watched the girls dance for a while and I suggested that it was time for me to go home. He then asks for a ride home. Everyone drives where I live, so I asked how he got there. Long story short, he rode the bus, because he has 2 DUIs. At this point I am committed to see this to the end, because I know it’s going to be a good story. As I’m driving towards his place, he lights a blunt, in my car. Scoffs at me when tell him not to. He continues until I say I’m kicking him out of my car. We continue to chat and he asks me to stop at a gas station. I think he’s going to buy me gas, since he lives 40min out of the way. Nope. I see him grab a 4pk of tiny wine bottles. Then as he’s at the register, I see that he’s buying condoms! Oh lord! He gets in the car and asks if id like you stop at a casino for a drink. We are still about 15min away from his place and I state that if we stop for a drink, he will have to find his own way home, because it’s getting late and I have a long drive home. He doesn’t mind. We stop at the casino and he wants to drink the little bottles of wine in my car, before we go in and cracks one open. I seriously laugh in his face. The police come through the parking lot, shining lights on the cars. Stops on mine. He says we better go in. Casually tosses the mini wine bottle out the door as the police move on to another car.

We go into the casino and we both order a drink. He is calling friends to see if they will pick him up. He has no luck. He orders another drink. As he is finishing his second drink, he asks if I will drop him off at a nearby motel. I agree. He asks for our tab. Before our tab comes, he calls his bank automated line. For some reason there is a problem. Interesting that he assumed there would be and called before trying to use his card, but it had worked 30min ago when he bought condoms and wine. This mf asks to talk to a manager. He complains about our perfectly adequate waitress, trying to leave without paying. At this point, I pay for our drinks, because that’s bullshit.

I take him to the motel. Not sure how he will get a room with his card issues. He asks me to wait, to make sure they have a room for him. I say yes, but just so we are clear, I am not stepping foot in that room. He laughs it off. He’s gone for about 10min and comes back and says he’s going to “check out” the room before renting, because it’s very expensive. He comes back a few minutes later and gets back in my car. He says he was there last weekend and now they wanted to charge him $30 more for a room of the same size. Uhm... ok, but you can’t come home with me. Where are you going to go? He asks me to take him back to the casino. I pull up to the door of the casino and don’t turn off my engine.

30min after drop off he texts to tell me what a great time he had. I respond with something along the lines of “That was the most unique date I’ve ever been on.”

A week later he text to ask me if I’d like to go on another date. I blocked his number.

/r/AskReddit Thread