I have so many that I just stopped dating because everyone is just broken, inept or falling over themselves when I meet them.
The best/worst one begins in a lovely town (decent-sized city) in middle-of-nowhere Texas. I had recently relocated there as part of that career-building experience you need to gain as an adult so you can earn more money and become a better person (so the saying goes). Guys at the plant told me that I was an instant Rock star and I had better be careful since I was single. Little did I know that truer words could not ever have been said.
I knew the stories about lots of single moms roaming around because of a more traditional way-of-life and lack of sex-ed in schools, but one of the first single young women I met was while I was staying at a hotel (since my residence wasn't finished yet and my job start date wasn't going to change). She talked about having two kids from two different guys and... then I saw that she was clearly pregnant. "Oh yeah, that's from another guy." I thought wow... she's cute but dumber than a box of rocks so no bueno here.
Fast forward a month or two after I'm somewhat more settled in to my new digs. I meet a woman from OKCupid. She seems nice, attractive, used to live in Dallas and moved back home to take care of family. Let's give this a try. Keep in mind, she's 26 and said she's divorced. So we meet-up at one of the better places in town and do the usual polite banter and walk in. She goes on about different things, including the job she used to have and how she likes the new one she started, but reveals that she has... FOUR kids! I was like uh... when were you going to reveal this on your profile? I'm OK with kids and want to have some of my own, but clearly she's done and told me she was. I'm not interested in taking on someone else's kids unless I get some of my own (I know, I'm a selfish douche). No second date, but she kept texting me several times a day until it finally stopped two weeks later.
Meet another woman from OKCupid. A few years younger than me, which is perfect, attractive, employed and mentioned that she too was divorced. I keep thinking, what's with everyone being divorced by their mid-twenties? Anyway, I went on vacation and we talked over the phone a couple of times and she seems eager to know when I'm coming back. I told her I was heading back tomorrow and we could meet-up later in the week. Inevitably she calls me as I'm about two hours away and we start talking - I have time to kill so why not. She really wants to come over to my place so I agree to pickup pizza and I have some beer in the fridge. We meet-up, I let her inside and we head up to the living room. I'm being a gentlemen getting her a plate, drink, napkin and fork and trying not to mess it up. We're talking and she throws out "you're attractive" while I'm getting settled down (after a long drive back). We start watching a movie and the "it's been a while since I had sex" comment comes up. Of course that results in insta-boner and I mention that things will change tonight. I pull down my pants, she gasps and says "OH MY!" and proceeds to start sucking. Eventually we make it to my bed and had sex for a while. After the end of round two, she starts asking me questions about how much my rent costs, how much money I make and other things that seem inappropriate for not really knowing each other that well. She tells me that she had one home that was foreclosed on and that her and her ex-husband bought another one that they intended to flip. I'm not the smartest guy, but I know what she's getting at - she's in deep shit and needs someone to help her out. I start getting a boner again and I had peeled the condom off because I thought we were done. She immediately jumps on my cock and slid it inside of her before I could say a word. It feels amazing - guys know what a tight, hot and wet pussy does to a man. She's grinding away and riding me like a rented mule. She knows I haven't came yet and she's working hard for it. I know she wants to get pregnant so I'll end-up trapped in that god-forsaken town and paying for her stuff. I held-back, told her to get off and she wouldn't. Tried pushing her off but that wasn't working either. She ended up cumming again and I didn't. Frustrated, she put her clothes on and started heading for the door. I said hang on, I know what you're trying to do and I can understand why. She said she appreciates that, promises to come over again because it was "really fun" and leaves. She never came over again.