At the tender age of 16 I was what most guys would be at that age: cocky, curious, and in decent shape. I had been in and out of the dating scene, but with a new car, an extended curfew, and an overactive libido, I decided it was time to open myself up to a more, “mature” relationship. That’s when I met her (for the sake of privacy let’s call “her,” “Jessica”).  Jessica and I had known of each other through mutual friends. She was a year and half older than me and a lot more experienced. Not necessarily in a sexual way, but more so in a relationship kind of way. We met one day in our biology class. She was the T.A. for the period before mine and stayed late to help grade papers. We got to talking and after a while exchanged phone numbers.

Before I knew it we were making out in my bed after a night of swimming in the hot tub and looking at the stars. My first huge mistake happened when Jessica told me she had to go and I pulled out a box of “her pleasure” condoms. Having lost my virginity just a year prior I somehow thought that was what all girls her age wanted.  She was offended (for good reason), and stormed out. I thought it would be the last time we would ever be together. I hated myself for a day or two until she texted me and said she wanted to hang out again.

Flash forward a few months later and I’m in a VERY committed relationship with Jessica. We were so madly in love with each other; promises of marriage, thoughts of moving away together after high school, and even matching Tiffany rings were just a few of the things that we used to prove to the world how “serious” we were. In reality, we were just crazy kids in love for the first time. So crazy, in fact, that I would sneak her into my house at least 2-3 times a week. I once even made her wait in my car while I had dinner with my family. She waited about 2 hours before I came back with a plate of food and told her the coast was clear.

A few months went by and the young, crazy flame of love was beginning to dwindle. Being so young and without much experience dating other girls, I started acting out towards her. I became interested in other girls and began developing serious feelings for one in particular. It was only a matter of time before Jessica and I were in my pool again, but this time it wasn’t hot tubs and star gazing. Instead it was Jessica “setting me free” as it were. She knew I wasn’t interested in her anymore and that I would probably never get around to breaking up with her myself. I was devastated.

Perfect timing for a breakup, as prom was literally a week later. I spent my night with friends having a great time, all the while keeping Jessica off my mind. That is, until she called me at 5AM hysterically crying. All I could make out was “Mike” (at the time one of my best friends) had locked her in the bathroom to tell her how much he was in love with her, and who then broke a mirror after she told him she wasn’t interested in the least.

I rushed over to the hotel they were staying at, met up with Jessica, and talked for about 2 hours while watching the sun come up. We talked about our relationship and how we both screwed up in one way or another. I still wasn’t man enough to admit to her I had done wrong, but I mentioned how sorry I was for being an idiot.

We kept in touch for the next couple of years. I went to college and she moved to Los Angeles for a while in hopes to jump start her acting career.  

Towards the end of my senior year, she returned home to go to finish up her degree and we met up a few times for coffee to reminisce. There were even a couple times we went out and ended up sleeping together.

Then, just last week when I was in Las Vegas (completely wasted), I got a call from HER. Of course I had to take it. We talked for about an hour but this time it was much different. This time it was her leading the conversation. She was upset with where she was in life, with her boyfriend specifically, and wanted me to cheer her up. The only thing I could think to do was tell her how much I missed being with her, and that if she told me she was going to break up with her boyfriend, I would drive to LA and propose to her. I might have been drunk, but I do remember hearing her saying yes. Before hanging up, we dropped the “L” word and she called me by the pet name she had called me throughout our relationship, “Bear.”

When I got home from Vegas I did some serious reflection. Would I really drop everything just to marry a girl I was so madly in love with in high school? Sad to say, but it was actually the longest relationship I have ever been in. That says something, doesn’t it? What was it about our relationship that would make me run back? Have I gotten over the whole “seeing other women” experience? Would I finally be willing to “settle down” and be with this girl for the rest of my life. One thing is for sure, it definitely says something that we stayed in touch throughout all these years, and that when either one of us is going through a rough patch we immediately call on each other.

One thing I learned throughout this entire experience was that you should always be honest with yourself and especially with your partner. You hurt yourself in the long run when you bottle up your feelings, only allowing them to spill out at a bad time—or even worse, have someone spill them for you. I learned that lovers can be friends, and that your friends don’t always make great lovers.  Most of all, I think I’ve learned that you should never give up on love. You never know when it will turn up again.

-Sam; 23, Tempe, AZ. Sam is a writer, musician, actor, and comedian. You can see more of his stuff over at  

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