How I Accidentally Dated Two Guys For A Year


Let me start by telling you I never meant for any of this to happen. I have never cheated and I honestly didn’t know I was cheating until about 6 months in to my split relationships. I’ll give you all the details, but I don’t really know how it happened.

I’ve never been the relationships type. Sure, I date, but that’s just about it. I go on a few fun dates and then I’m bored. I was the girl who always put my education and my career first. I’m your typical type A personality with a checklist for my future that doesn’t feature a man.

Just over a year ago I began a fabulous new internship with my dream employer. For once in my life everything seemed to be going my way. I had just lost a considerable amount of weight, my grades were killer, and I had a dream job- how much better could it get? That’s when I met John*.

I’m young. This internship was my first “real world” job where all the men wear suits and the office closes at six. John worked in the office above me and I was shocked to find out he was also a student at my university. He hit me like a brick wall with his perfectly tailored suit and adorable little smirk. He was charming and pulled together and I was on cloud nine when he asked me to come to a fight with him one night after work.

Me, being my oblivious geeky self, had no clue John had meant to ask me on a date, but it became blatantly obvious when he kissed me. It was the worst kiss ever. I reasoned that it was a sign that we weren’t meant to be together (something in our work policy anyways) and that we could just be friends.

A little over a week later I began working at an apartment complex to supplement my miniscule intern pay. In the interview Tony*, the manager, and I really hit it off. I shrugged it off and assumed his flirty comments were just part of his boyish charm. This soon proved not to be the case when we went to a movie premiere together with a few of the other managers. Once again, oblivious me didn’t realize this was a date, but I soon found myself crushing hard for my new manager.

A few days in to my new job, Tony had me come over to talk about some work stuff and in a move that shocked both of us, he kissed me. And unlike the god-awful kiss I shared with John a week earlier, this kiss sent shivers down my spine. We started spending every waking second together and before I knew I was involved in forbidden office romance.

There was just one little problem: Tony was thirteen years my senior and had a kid. I knew my parents and my friends would never approve so I kept my blossoming romance on the DL. Meanwhile everything at my internship was moving much faster than I thought possible. I made friends with all my coworkers and before I knew it I had been promoted from my intern spot. I spent evenings at Rockies’s games with my coworkers and with John. John and I shared a deep love for baseball so we would try to hit at least one game a week, but, in an attempt to not give him the wrong idea, I made sure we alternated on who paid for the tickets and dinner.

My life was perfect. I’m not the type of person to say stuff like that and I don’t take it lightly. I didn’t realize that there was a problem until I got offered a summer position across the country, leaving me with just over a month before I had to pack up and leave. When I told Tony he was supportive and excited. He promised that we would be fine- our love could make it though anything.

Unfortunately Tony’s actions spoke much louder than his words. Anytime I needed to run errands, pack, or spend time with other people he would guilt me about leaving. I remember spending most nights crying and honestly contemplating turning down the position. I was so enthralled by Tony that it never occurred to me that what he was doing wasn’t fair – he knew from the moment he met me that work would always have to come first, especially when it came to opportunities like the one I was offered.

John handled the situation oppositely. Despite the fact that he was competing for the same opportunity, he congratulated me with flowers and a sweet card. He wished me the best and told me that no one else deserved the position more. He spent the entire month encouraging my decision to take the job in Washington, D.C.

One evening at our weekly baseball game John asked me to attend a wedding with him. I panicked and said yes – mostly because I love weddings but also because I really wanted to go with him. I hadn’t noticed until that point that all Tony and I did was hang out at his apartment and I missed going out.

The wedding fell just a week before I left for my new job and John and I had the most amazing time. He kissed me again, but this time his kiss left me wanting more. We danced all night and at the close of the evening he whispered in my ear to tell me he felt like the luckiest man there.

I’ve never felt so guilty as I did then. My perfect little life felt as though it was crashing around me as I started to see that John thought we were a couple. I drove straight to Tony’s apartment, cuddled up in his arms, and tried to forget about everything. A week later I didn’t so much as say bye to John before I left for the summer.

My summer in Washington, D.C. ended up falling way short of expectations. My dream job was a nightmare, I missed my family, and my housing fell though (twice). Every night I would call my mom and end up bawling my eyes out. I would call Tony, but each time he left me feeling even guiltier for pursuing this position. One night when I was telling him how awful my day was and how much I missed him he snapped back, “Well you deserve it. You chose to leave me.” He then spent twenty minutes threatening to end our relationship. I spent all night crying.

I didn’t call John a single time while I was gone, nor did he try to call me. We would exchange a few texts back and forth but I figured anything we had, or he thought we had, was over. Then I received a package in the mail. It contained a CD from a concert we went to together (a band I had never heard of but became my new favorite) with a note using a silly pun from one of their songs. A few days later I received a card from John with a heartfelt message saying he was counting down the days until I returned.

I stopped feeling guilty right about then. My relationship with Tony was on the rocks, but John was still there and still being supportive. I returned home from my summer position just before John’s birthday and we went to an all day music festival to celebrate. Everything seemed right and I was happy to be with John. Then I saw Tony for the first time. Queue guilty conscience.

Tony and I went back to the way everything was before I left. He would only occasionally guilt me about leaving and I stated to tune out John again. John and I would occasionally still meet for coffee or lunch or outlet shopping (our favorite thing to do). Memorial day weekend John and I were enjoying our a day of shopping escapades when my parents called and invited us out for a barbeque.

I’ve always been extremely close with my parents, but they hadn’t met either of my love interests and I liked it that way. Unfortunately John overheard the phone call so I had no choice but to invite him over. From the minute he walked in to my childhood home, it was like he was part of the family. My parents adored him, my brother spent half the night talking sports with him, and my little sister couldn’t stop giving me the “He’s so cute!” look. I kept assuring my parents that John was just a friend but it was too late.

Damn it.

I should have broken things off with Tony right then and there. I know I should have. But I’m selfish. I loved Tony…and I loved John. I couldn’t stand the thought of losing either of them. I kept thinking that my normal destructive tendencies would kick in and eventually one of them would break up with me.
They didn’t.

Then the holiday season came around. Let me just tell you, I have no clue how I pulled this off and I don’t recommend it for anyone. I invited Tony and his daughter out for Thanksgiving dinner and introduced to Tony to my parents as a friend. I avoided the topic of holiday dinner with John until the last possible minute and then told him I had invited Tony over because he had no family and his daughter asked if we could spend the day together (Side Note: Tony’s mom recently passed away, his dad is out of state, and his sister was having Thanksgiving with her husband’s family. He really had nowhere to go). John was clearly upset but I tried to ignore it. It got a little harder when my mom asked me why I hadn’t invited John, stating, “it doesn’t feel like Thanksgiving without him.”

I made up for Thanksgiving by inviting John over for Christmas. Tony hosts Christmas every year for all of his friends that can’t go home for Christmas. I stayed over Christmas Eve and left early Christmas morning to spend Christmas with my family and John. (Another side note: my parents really liked Tony and his daughter, but they loved John. They were so happy when I brought him for Christmas.)

This trend continued with New Years and Valentine’s Day. New Years is my parent’s anniversary so I told John I had plans with them when instead I spent the evening with Tony. My job requires I attend a lot of events so on Valentine’s Day I told Tony I had a work event and spent the evening with John.

I know… I’m an awful, awful person.

To further illustrate just how fucked up this situation is, let me divulge some highly personal information. Tony and I began sleeping together (constantly) within weeks of dating and within a month I was spending almost every night at his place. John, on the other hand, had never gotten past first base. Yet there he was, loyal as ever and the sweetest guy.

John would bring me flowers every week and send me cute text messages throughout the day. I started relying on the stark differences between the two men in my life to equalize my love life. I got to play house and have amazing, hot sex with Tony and I then I got all romance a girl could ever need from John. Their personalities differed vastly too. Tony is a complete man-child. He helped me let loose every once in a while and I knew I could spend all night laughing. John was an intense, but very sweet go-getter and helped me keep a level head and plan for my future.

To make things worse, I started considering law school. John and I both have law school dreams so we traveled to a few schools together. Meanwhile Tony spent all his time making me feel like shit for considering moving for school. He even used his daughter as leverage in fights because she made it impossible for him to follow me to law school. To add on to everything, my mom visited me at work and told a gossip-loving coworker all about John and I and how she should “start planning the wedding.” Our secret romance was soon common knowledge at work.

I’m now in a position where I will have been with both guys, one knowingly and one not so much, for a year. And I can’t seem to leave either of them. Before you start judging me too much- I know what I should do. And I know that my actions have deemed me not good enough for either of them. And I hate myself (most the time) for it. While one guy is giving me a key to his apartment, another is talking about buying a puppy together and moving in. When I’m sending a goodnight text to one, I’m cuddling up with the other. I am an accidental whore.

I’ve never told anyone about this. And I don’t know why I am telling all of you – I guess I just needed to get it off my chest. So thanks for listeåning and thank you to everyone who isn’t in complete hate with me now.

And because all of you guys are now stuck in this disaster with me, I promise to give you the all the dirty details to come.