The Loser I Dated Before I Realized I Needed to Start Dating Older Guys: Part 1

At the young age of 18, I met a guy named Jared while on a trip I took with my mom and sis­ters. At six feet with dark brown hair and eyes, Jared wasn’t exactly the dream­boat I wished for. He was a guy who didn’t fin­ish school and was unem­ployed, still liv­ing with his mom. That doesn’t look good to any mother, espe­cially one with a daugh­ter who was unem­ployed her­self; so my mom def­i­nitely had some doubts about us. But what my mom didn’t under­stand was that where she saw a good-for-nothing guy, I saw a poten­tial “dream­boat,” just one that needed a bit of work.

I gave my vir­gin­ity to Jared around the time that my birth­day came. It was sup­posed to have been roman­tic and per­fect, espe­cially since Jared came down to see me a month after we had left Ore­gon. Giv­ing over my vir­gin­ity was a deci­sion made under that hot and heavy haze where all judg­ment was out the door and the only thing that one wanted to do was get their release.

I was in bliss for all of 10 minutes—and cue the humil­i­a­tion. Once he came, it was over. He kissed me on the cheek, said his oblig­a­tory “I love you,” and turned over to go to sleep. I was mor­ti­fied. That was it? I had prized my v-card as some­thing to give over to some­one who was worth it. The idea of being inti­mate with a man always filled my mind as some­thing that was amaz­ing, sen­sual, and mind blow­ing. The only thing that blew my mind with Jared was how he didn’t even know that women came, too.

Regard­less of the humil­i­a­tion that I suf­fered at the hands of Jared, I was still in my first puppy-love stages. There­fore, when he invited me back to Ore­gon with him, I was ready to jump in his car and drive 14 hours to another state by myself. It turned out to be the best and worst idea at the time. You can learn a lot about some­one by sit­ting in the car with them all day.

I ended up spend­ing two months in Ore­gon. I was with Jared and we had a lot of laughs and good mem­o­ries, but the bad mem­o­ries always out­weighed the good ones. I had tried my best not to let my inse­cu­ri­ties come out, but it was hard when Jared was noto­ri­ously known for being a player; although he swears that he was not with any­one else around the time that we were together, I always had my doubts.

There were days that we’d wake up late and he’d imme­di­ately jump in the shower, get ready, and have a friend pick him up. I had no idea where they went, but I never asked. I was too proud to even show a vul­ner­a­ble jeal­ous side to myself, so I let it go. But soon it became one too many times and I started to reeval­u­ate our “rela­tion­ship.” This guy wasn’t ready for a com­mit­ment and I was. But it would take a lot more than bad sex to con­vince me it was time to move on…