Dating Series 3 of 6: Jessie

Meeting Jessy

Note: Names have been changed.

This is where things got complicated...

The years passed, not much happened in high school in regards to dating. There was not anyone I was really interested in to be honest. Then I moved to college and my first semester I met a friend of my roommate named Jessy. Jessy was a very confident female, who knew she wanted to go places in life. She had a rough childhood and was working on making her life better. Jessy wanted to be a nurse, maybe even a doctor. Jessy also had a hard time with guys. She would get lost in her infatuation of them, find out they were jerks, and then the relationships would end abruptly.

Nothing really happened the first semester I was in college. Everything was too new for me and I didn’t know how interested I was until halfway through the second semester. We would chat online on AIM about life and faith. She was smart and had such a heart for God.

Toward the end of my freshmen year, I thought about asking her out... but we were both going away for the summer and it didn’t really seem all that logical to take that next step, so I decided to wait until the new school year.

Does anyone even remember AIM anymore?

And that is when things got better... and worse. We kept on chatting online late into the night when she wasn’t working and I was online. I got her number and we talked on the phone a few times.

Then one day she was excited about something and wanted to tell me. Can you guess what? Well she was working at a summer camp and fell for this guy. I played nice but I was disappointed. Here I was taking this time to know her and planning my approach when this guy just swoops in and things happened.

We still chatted online and on the phone; however, we talked less (obviously) since she now had her boyfriend. A lot of chats consisted of us talking about God and about her boyfriend. Then, right before my sophomore year, and after her job for the summer ended, it happened. She caught him with another female while she was talking to him on the phone. What a douche, right? She felt so betrayed and I did feel bad she got hurt... but finally I thought, the time is coming to make my move. I couldn't wait much longer.

When we were both back on campus, she came to meet me in the dorm lobby. I was so happy to see her, we said hi, and hugged. I still remember she was wearing a green shirt. I was so into her at the time. I knew I couldn’t keep playing the friend card. I wanted more out of our relationship. I had to let her know how I was feeling. Besides, not telling her was driving me crazy.

The next few months became a blur. We hung out once, we went to eat at Olive Garden and then saw a double feature of Men in Black 2 and Spider-Man. It was shortly after we were talking on the phone when it finally came out.

Men in Black, Killing Alien Scum On-Screen Since 1997.

She was talking about friendship and how my roommate (her old friend) didn’t talk to her that much anymore, in comparison to myself. Then it came out, that I liked her differently than he did... and bam, I think the relief I felt in telling her was great for me... but I think it was really confusing to her and became a burden on our friendship or more-than-friendship or whatever.

She thanked me for being honest, said she wanted to be friends, and she would let me know if she felt like moving our relationship from friendship to something more. The more never happened, and honestly, things got really weird.

The truth was we got a lot closer, we would talk late and meet up. I remember we would try to save a seat for the other in the chapel services… but we always seemed to miss one another. We never did wait for the other, which I think is telling looking back.

There was something missing there, something I guess I didn’t see and maybe she didn’t see. I don’t think we were ever really on the same wavelength. It seemed like I felt we were in the beginning of a relationship and she felt we were just really close friends. This lasted a while, for about two months. I didn’t feel like I was being strung along; however, the reality is I was being strung along. Now looking back, I think she liked having someone she could talk to but there was no commitment on her side and no chance of being rejected on my side, so things continued like that for a while.

We had fall break at the end of October and I was going to stay with my roommate in his town. Jessy lived really close, so I decided to ride with her there, hang out for a while, and then spend time with my roommate that weekend. Little did I know her whole family was going to be there and I was going to be invited to dinner. This seemed like more than friendship, right? I was meeting the family; yet, she introduced me as "my friend". That phrase stung and confused me.

Let's Hang Out = You Can Meet my Whole Family at the Mexican Restaurant

That weekend turned out to be the deciding factor in our friendship/relationship. We were supposed to hang out together the next day but she blew me off and then she wanted to drive back to college by herself. Signals anyone? I was getting the cold shoulder

We were back at college a week later and she would try to chat with me online. I asked her to call me on the phone and finally asked her point blank: Do you like me that way, like a boyfriend? She said she didn’t want to hurt my feelings, but I got her to finally tell me the truth: NO. Those words stung, they hurt, but I was glad to finally get a answer.

The rest of that semester and the next I was pretty depressed. I gained back all the weight I had lost my freshman year. I tried to be friends with her... but it never worked. She would ignore and not return my calls and I wouldn't stay up until 2AM to chat with her online anymore.

She told me online in a chat that she was sad things were different, but I asked her what she expected. I got the feeling she wanted a friendship on her terms only. We stopped talking, she began to fade into my memory, but I was still pretty bitter about the whole thing.

I saw her go out with some dope the next year as a junior and that was the thing that finally set me free. Later, as I reflected on this whole situation with my roommate, who was her old friend, he confessed to me that she had called him one day and told him she did, in fact, like me in that way. He was confused why she had told me otherwise.

I had always figured she wasn’t attracted to me, but maybe she didn’t want to commit, maybe she was scared. I don’t know... and now I don’t really care. I look back on this as my first real attempt at a relationship and it taught me how to stand up for myself, but also how females sometimes can and do string guys along as emotional support. I think, in some way, perhaps I was everything, ideally, that she wanted in a guy, yet either she was not truly attracted to me physically or she was scared about being with a guy who had depth.

What relationship was the most complicated for you?

What are some complications you have had in your past relationships?

~ Doubledb