Horrible fuck ups I’ve made with girls/women over the years

As I’ve mentioned before, I have very low self esteem about my appearance. Growing up, I had very little money most of the time and this further contributed to my low self esteem. Because of these factors, I dated very few girls. Within the past year, my self esteem and money situation have improved, so I’m more willing to socialize and put myself out there. I go on dates more often and hook up every so often, though I still have to pay for sex. Anyway: here’s some very serious fuck ups I made with girls over the years.

#1: Melissa: when I was 7 or so, I lived in an apartment building. Just down the street was a single mom and her two daughters. My grandmother befriended this woman for the purpose of getting me rides to school, since me and Melissa went to the same elementary school. Melissa fucking hated me, but she went to the facade of being my friend to reduce conflict. At my apartment building, there was a very long driveway where all the kids played. One of these kids was a mentally deficient, obviously gay black 5 year old. One day, there was a pretty girl among us and he made fun of her by saying “Kiss the girls.” Anyway, the next day, me and Melissa were walking back to my apartment and that black kid was there. Once again, he said, “Kiss the girls.” Melissa got pissed and said “You better not.” Here’s where I fucked up: what I should have done was afterwards when we were by ourselves, I should have said “I’m sorry that kid embarrassed you like that. But, I think you’re pretty and would really like to get my first from you.” She almost certainly would have said no, but I think she would have let me down easy to continue our friendship.

#2: Helen: I went to three high schools. The second one was mostly Asian and I joined late in the semester, so I had a hard time making friends. On my first week, I was standing by myself and a very pretty girl that was a mix of white and Asian (Helen) walked by with her ugly, chubby Mexican friend. Helen immediately befriended me and let me hang out with her. I liked Helen, and she was nice to me (at least to my face), but the thing I hated about her was that she was a conceited bitch and talked shit about everyone at the school. Here’s how I fucked up: I had so little money that I couldn’t afford a fucking date, but one of the roommates at the place I lived at was relatively nice to me. I should have gone up to him, explain the situation, asked for money, and offer to repay him with chores and favors (which I did for him anyway). So yes, I never went out with Helen. The next year, she apparently went to USC (I was a freshman when we met). That year, some guys came up to me and said, “Oh, Helen was asking about you. She was wondering how you were doing.” So yes, she most certainly would have gone out with me.

#3: Kibe: This was at my third high school, which was mostly Mexican. I shared a class that had a pretty girl named Kibe (you can’t put accents on this site. Her name is pronounced “key-bay”) Everything about her was good, except she had a lot of acne. Still, I found her very attractive. In that class, our teacher would give us questions to write about in journals, then we’d turn them in and he’d read them. I have no clue why he didn’t talk to her alone about this (though he was nice so I don’t think he made this mistake on purpose), but I overheard him talking to her and he said “Kibe, I read your journal. You’re not ugly. You shouldn’t focus so much about your appearance. But again, you’re not ugly.” I should have thought about this and realized “Hey! Kibe must be single and have low self esteem about her appearance. Maybe she’ll go out with me!” I most certainly should have talked to her alone after class and said “Kibe, I overheard you talking to Mr. W. I don’t think you’re ugly at all. Are you doing anything after school today?” Unfortunately, I didn’t. At a later date I was talking to her by her self and she was wearing a very tight dress that showed off her curves. I should have flirted with her and asked her out then too.

#4:Emma: I shared a class with Emma and we sat next to each other. When the teacher gave us quizzes, we would trade papers with the person next to us and grade each other’s papers. Emma was an underachiever and didn’t try very hard. Despite this, I still helped her out and wrote in the correct answers for her quizzes. She told me, “You don’t have to do that. I don’t care.” but I did it anyway. One day next year, Emma and a very fat annoying girl came up to me at lunch and Emma said, “Say, there’s a United Students meeting right now (the United Students was a liberal political activist group on campus). They have pizza. Do you want to come with us?” Again, I fucked up and turned her down, partly because I really hated being around that fat annoying chick. Still, I suppose that meant Emma was willing to go out with me.

#5: Mary: I was working at a department store in San Diego. Due to money, I never once tried to go to Sea World with a pretty girl (I mentioned Sea World in another topic; that’s why I was thinking about this again). I was 21 at the time and Mary was in her late 20s. One thing I liked about her is that on multiple occasions, Mary’s thong was hanging out even when she wasn’t kneeling or bending over. She was married and had kids, but anyway, we were one day talking about Sea World and she said she had season tickets. However, she also said, “I’m getting sick of the fucking place!” What I should have done is said “ I haven’t been to Sea World since I was a kid. I know you’re married, but I would still like to go with you as friends. I’ll pay for the gas and food; and you just have to let us in with your season tickets.” If she would have actually said yes, then I would have enjoyed getting soaked with her. If the “date” were actually going well, I would have asked her if she wanted to stand under the tank as Shamu comes by to get drenched in water. I would have held her close to me and I think I would have had a good time with her (though I am a little curious what she looked like without makeup).

Anyway, sorry if that was a little long.