Dating, It's Complicated Dating, It's Complicated
 

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Jason

Dating, It's Complicated: Issue #14

Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me at dating.itscomplicated[at]gmail.com!

I’ve been dating a girl for nearly 2 years now. However, early into our wonderful relationship there was a bit of a mishap. We’d been together for a month or so and hadn’t had sex (She was 14, and I was 16 at the time). My parents were leaving for a fancy Chinese dinner one night. Taking advantage of this golden opportunity I poured up some wine and decided we’d take a dip in the hot tub in my folk’s room. Everything went smoothly, even better than I could have imagined. We had gotten off with it and my parents even brought us home milkshakes afterwards… 5 minutes later there is a roaring noise coming from my parent’s room. Little did I know but the hot tub “jets” turn on 30 minutes after the tub empties to dry/remove any excess water. We were promptly busted by an infuriated, red-faced mother.
-Jared

A couple years ago when I was dating my ex, he told me he didn’t believe in medication and that I shouldn’t be on it. I’m bipolar. So when I went off it I had a total breakdown, and crying over the phone, I told him, “This is who I am. Do you still love me?” He was real quiet for a moment, then: “I think you should get back on your medication.”
-Anonymous

While talking with my girlfriend the other day I found out that she has never seen the movie Jurassic Park. Upon hearing this I immediately insisted we watch the movie that night, no exceptions. Time goes by and we watch the movie, all the while my girlfriend seems really concerned at the sight of the dinosaurs. I thought nothing of it until the movie ends and she turns to me with the most sincere face and says “That didn’t really happen did it? Dinosaurs aren’t real right?”……. I’m dating a moron.
-Dan

I had been in love with my best friend for four years, him feeling the same way all along. I was always reluctant to date him, because I didn’t want to risk losing our friendship. He was the only guy I had ever trusted and I cared about him more than anyone. I finally decided we should be dating, seeing as we loved and trusted each other: what could go wrong? After two weeks, he cheated on me with a girl he met on a bus.
-Jessica, CA

I was dating this girl online for about 6 months, earlier on she sent me some pics of her and I thought she was pretty cute. Then while I was on a forum that linked a lot of hot chicks, someone linked pictures of my girlfriend at the time. So I confront her and it turns out she was a scrawny kid in New Mexico who was gay. Yeah.
-Ryan

My girlfriend got mad at me because I was dancing with “some girl” while I was at a bar with some cousins. The “girl” was one of those cousins…
-Anonymous

About at week ago I had sex with an ex-boyfriend of mine. It was amazing sex, the kind of sex you tell all your friends about. After we fucked we went on to his porch for an after sex cigarette, you know, to get the taste of dick out of your mouth. Well then I say something about how this is my first time with a guy in months, because I’m bisexual and I have been going through a penis drought. Then he turns to me and says “Yeah, I’m pretty sure I’m gay.”
-Anonymous

My freshman year my roommate’s girlfriend would always text me saying that she wanted to hook up. I didn’t bother because I was in a relationship at the time. One weekend my roommate was out of town and I had just broken up with my girlfriend. While I’m out partying I get a text from my roommate’s girl, I finally give in and tell her to meet me at my room. After a night of wild sex we decide to go at it again the next morning. As I’m about to cum I hear my door being unlocked and my roommate walks in while his girl is riding me. This guy was a short but stocky wrestling type and he proceeded to beat me mercilessly while I’m wearing nothing but a condom. He was able to switch dorm rooms citing his reason as “Doesn’t respect my property”.
-Franky, Chico State

I was dating this girl in high school for about 4months now. She had a babysitting job and I would go over sometimes at night for a little late night romance while the kids were asleep, they were 2 and 4 so they went to bed early. Well, we got really hot and heavy and started to get into the dirty if you know what I mean, so she then tells me to make love to her over the coffee table. These people we’re rich mind you, and that coffee table looked pricey, but when in the mood, what the hell. So I proceed to make love to her over the coffee table when we hear a noise from upstairs. This scares me and I fall forward. Pushing my girlfriend and me through the glass coffee table, shattering it to pieces. Turns out one of the kids was awake because he heard his parents pull up in the driveway…they came in 2secs after the incident to see me and my girlfriend naked and a shattered coffee table. She lost her job…I lost my girlfriend…
-Josh, Windsor Ontario


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Whiny inmate

I worked at a prison as a corrections officer (prison guard) and there was a particular inmate there who always complained about everything. For three months I endured his rants on how the lights were too bright, the rooms too hot, the blankets too scratchy, and so on. Obviously this is prison and no one gets luxury accommodations. I reached the end of my rope one morning... Read More » when I had to go down the run and wake him up at 7 AM for transport somewhere else in the state for a medical procedure. The guy is all grumpy, complaining about how I'm getting him up at the "ass crack of dawn." He demanded to be allowed time to take a shower, heat and drink some coffee and have a smoke. The van taking him away was already waiting for him and I knew for a fact that he'd taken a shower before going to bed the night before. I told him there wasn't time for any of that, he just had to get dressed and get to the van. He begins swearing and ranting about how inhumanely we were treating him and after months of his complaints I couldn't hold it in anymore. "I know, it sucks how early you have to get up to get your free medical care, huh?" I told him. He was immediately silent . He got dressed and left in a huff. I later found out how he wrote a grievance to the warden about my comment. Inmate complaints are occasionally reason for worry, so I was nervous when the warden called me in to his office. It turned out he just thought my comment was hilarious and told me to keep up the good work.