’20 Times A Lady’ Winning Entry No. 4

Thanks again to Karyn Bosnak for writing such an entertaining book, and to Harper Paperbacks for sponsoring the contest.

Also, thank you to everyone who send in their “Worst Old Boyfriend” stories. Here is the fourth winning entry from “20 Times A Lady” contest.

Well, Greg was his name and insanity was is game. You know how ever girl goes through that, “Oh he’s perfect! I just have to do a little tweaking but in the end I will have the perfect man!” phase? I think I was delusional with it. That is the only way to explain why I went out with this boy. For a year and a half maybe I’m the one who is insane.

Anyways, how we met? He was a friend of a friend. The only thing I knew about him was that he was in a mental ward at a hospital. Yeah I’m not kidding. So I met him one day after he had gotten out and he was out with his friend who was my friend. We hit it off for some reason, he thinks it was because I liked football, but really it was because he was gorgeous. Great body, hot face and short black hair, who wouldn’t be smitten? I wondered to myself how someone this attractive was crazy, and what kind of crazy? Like, ‘aliens have probed me in the ass 97 times’ or ‘I want to kill myself’ crazy. Turns out it was the latter that was true.

After we had hit it off, I invited him over to my house and we got to talking. He told me his whole story. How he tried to kill himself 3 times (violently I might add yeeash) and how he was diagnosed as bi-polar, which is really rare at such a young age (17). Here is where the, “Oh, I’m a healer, and wouldn’t it be a wonderful story for our children if he could say that I was the one thing in his life that went right and I lifted him up and cured him,” woman-type thinking came in. I felt bad for him, and I guess I took him under my wing and between my legs. (The fact remains that he was still gorgeous ok people?)

So we started dating, and I found out that he apparently had cheated on every girlfriend that he had ever had. Well, more irrational woman thinking happened, something along the lines of, “Oh, well I’m different, I’m special”. So we kept on trucking. Six months had passed, and he did not seem depressed, so look, I was helping! But, then came the ditching. I was ditched from dates, dances, concerts, you name it and he opted out of it. However, we still stayed together.

We made it through Christmas, and I got to go to Florida, how romantic. We made it to one year. Major problems happened here. Unknown to me, this is when he cheated on be 3 times, twice with one girl and the third time was with that same girl again and her friend, at the same time. What a sleaze. And they were both ugly. I mean at least give me some credit and got for someone more attractive! So he lied about that for a while (8 months actually, until I finally confronted him about it when someone told me the whole story 2 months after we had broken up) We broke up after our one year anniversary for four days, and then yes, got back together, why, I still don’t know.

We got through the summer, and then I went to school. We lasted a week into school and I dumped his ass. Finally. He cried, told me that he would never love anyone again and that he was probably going to kill himself. I told him not to threaten me to get me back, and hung up. I found out that two weeks after he said he would never love anyone again, he was in a full-blown relationship with some younger chick that was 10 times less hot than me. Well at least he down-graded.

To summarize, I dated a guy who was in a mental hospital for a year because he was bi-polar and tried to kill himself 3 times, he was a perpetual cheater, he ditched me, he bought me flowers twice in a year and half. At least I can’t do any worse right?

Tags: Contest