Why Am I Like This - A Series of Bad Decisions

The First Boyfriend: The Good

2015

I met Conlan for the first time at seventeen, halfway through my senior year of high school. He had just started seeing Meghan, who had since shown her true colours as a crazy bitch, and the three of us hung out a lot. One night, I crashed a date night of theirs and we were watching a movie when the topic of my graduation came up as it was just a few months away. I knew I didn't want to bring Meghan to the dance as a friend date but I also didn't want to go alone. I casually asked Conlan if he'd be my date and he accepted, Meghan wasn't the most impressed but she also understood that we were good friends. At the end of the night Conlan drove me home and we spent probably four or five hours sitting in the car just laughing and joking around taking silly snapchats and sending them to his friends.

From then on Conlan and I's friendship grew and we were hanging out almost everyday, texting all night, going for drives around town belting Eminem in his car. The more we hung out the more my friends pushed that we should be dating. At first I called them crazy he was just my best friend but after hearing it enough I really did start to develop feelings and I had no idea what to with them. I had such low self esteem that I couldn't fathom a world where a guy as cute as Conlan was would ever like me.
One afternoon after school we were hanging out at his apartment (he moved out of his parents place the year before as soon as he turned 18) and his roommate made a comment about us fucking and I laughed it off and nonchalantly looked over and said to Conlan how crazy it was that everyone just assumed we were together. He got serious and asked if maybe we should be dating. I freaked out and the paranoid part of my brain told me it had to be a joke. I left.
The next week we were at my house and I decided it was now or never to shoot my shot and as we watched a movie in my basement I leaned over and kissed him. After a few seconds he responded and kissed me back and just like that I had a boyfriend. It was a whole new experience for me. Having someone to really care about me and wanted to talk to me everyday and would help me get through my struggles. It was amazing.
Three months into dating, I decided I was ready to have sex for the first time. I was on birth control already and I knew it was time. We went back to his apartment and he was so gentle with me. But I guess I was nervous because my vag said not today sis and he couldn't even fit himself in. The next morning we decided to try again and this time I was able to relax a little more and we got it to work. It was so awkward and hurt a little bit but I thought it felt good and was something I knew we'd be doing a lot.
It wasn't long before I was basically living at his place, we would spend 6 nights out of the week together at his place making obscene amount of taco salad. We were a real couple in love. Though those words were never spoken. I could feel that he loved me just the same.

Lesson Learned: Maybe I'm not as ugly as I thought