Welcome to Rough Love, the column where we share your craziest, funniest, most embarrassing dating related stories. If you think you can top this batch of rough loving, submit your story at the bottom of this page.

I Skyped Her Boobs

When my now-ex and I were in Highschool and about to go to seperate colleges, we decided to give long distance dating a try, but she had never heard of Skype or video chatting or whatever. One day I download Skype on her laptop and go back to my house to call her and show her how it worked. When I call her, she immediately gets mad at me because she insists I am blatantly staring at her chest and not looking her in the eye. I spend 10 minutes explaining to her that the webcam is above my computer and if I look at that I wouldn't be looking at the screen and so by looking at the screen it looks like I'm looking down, but really I'm looking at her. She finally gets it and apologizes and makes it up to me with some REALLY kinky good-bye sex before we went to our respective colleges... The best part is: when I called her that first time her web cam wasn't positioned right and all I could see on the screen was her chest. P.S. 36 DD - Anonymous

In high school my (ex) girlfriend and I were very... promiscuous. Apparently my mom found out and decided to have a talk with me one night though I assured her I was still a virgin. After class ended we came home and went about our usual routine of stripping on our way to a random room in the house after bolting the front door. About five minutes in my mom walks through the garage door (into the house) asking why the front door was bolted only to stop mid-sentence and walk into another room, staring at the trail of clothes in the process. My mother thinks I lost my virginity doggy style in the living room. P.S. She should have mentioned she had a doctors appointment instead of work... - Anonymous

So, now that we're finally broken up, I can tell everyone how SMALL my ex's penis is! Seriously, it was so small that I had to comfort him about it. I would tell him that the because of its size, I didn't have to be fingered or anything to open up, so sex could be more about him. And the sad part is that it was true. Sex was a chore, and I had to masturbate almost every night I was so unsatisfied. So if you meet a tall, skinny, self-absorbed, ASSHOLE!!!! who goes to VCU, he might be the small penis guy. BEWARE! - Anonymous

So there's this girl I was trying to get into a relationship with, things were going fine but i kept telling her how i felt about her while I was drunk, but she blew it off cause I wasn't sober, so two days before I was gonna tell her how I truly feel about her, she had a long time friend over we all were drinking and she tells me she has feelings for the friend after having him in the friends zone for a long time, so doing math i realized she known him longer and I went on a self destruct mode with vodka, but unfortunately this chapter in my life isnt finished so im still trying to figure out what to do(still tell her or walk away). women cant live with them... cant fall asleep without them! - Anonymous

One morning my boyfriend and I were hanging out in the guest room at my house, where he usually has to sleep when he stays over. He comes across as really gentlemanly and well-behaved, so my mom usually trusts us to cuddle in there in the mornings with the door closed. Naturally we take the opportunity to fool around a bit, until my mom calls though the door asking us to get up and be sociable because she doesn't want my younger sister to think it's okay to have boys in her room with the door closed and all. Being a nice obedient daughter, I started getting up and asked him if he'd like pancakes for breakfast. This sweet, decent guy looks at me with adoration in his eyes and says, "Forget the pancakes, I'd rather stay here and poke you in the vagina some more." - Anonymous

About a week ago, my girlfriend and I were at a mall, when we somehow got onto the topic of geography. This lead to about half an hour of me convincing her that Alaska was next to Canada. The weird thing is, I tried to get get about 4 people to back me up, and each one of them thought it was an island near Hawaii. Is it really that rare to know where Alaska is? - Anonymous

Once, my ex-boyfriend came over after school and no one was supposed to be home for a few hours. We started having sex, he was on top, and all of a sudden, he stopped and started to ask, "where is your bathroom?" all he got to was bath before he threw up all over me. That night, my mom proceeded to ask, "why does it smell so bad in here?" - Anonymous

Last night I met a girl and took her back to my dorm. My roommate is at his house this weekend so I have the single room all to myself. We started having sex and although I promised Jon we would not do it in his bed (which we didnt) we were forced to have sex on the floor which isnt so bad. however we did sleep in his bed because no girl wants to sleep on the top bunk. Sorry Jon! - Anonymous

My ex explicitly told me (many times) not to make big life choices based on her, and i understood - that puts a lot of pressure on a relationship. So i apply for a job where i'd be traveling about 35% of the time. Having not even gotten the job, she tells me my decision to apply for it has really hurt her, and while being hurt/pissed, and before having any opportunity to work it out, she's met a new guy she's into - so we should break up. Dating's complicated.... - Anonymous