I Was Dating Two Guys At The Same Time, But Karma Caught Up With Me

I had been single for close to three years and I almost lost hope in finding love until my luck seemed to turn around. I met two guys who were interested in dating me. After my divorce, I suffered immense emotional damage that made me unable to commit to another relationship or even entertain the thought of it. I was okay with it for some time but my family and friends felt like it was best for me to move on and try to have another relationship. After all, I was only 32 years old.



When I turned 35, something in me changed. I regained my confidence. I was more lively and I started feeling like myself again. However, I still hesitated to start dating. Until one day, I met Dan. I was leaving work and we bumped into each other at the elevator. Though I had seen him around, we never interacted before that day – not even a hello.

“Headed home?” he asked.

“Yeah. You?”

“No. I have some pending work. I’m just going for a quick coffee break then I head back to the office. Do you mind joining me?”

Before I knew it, I was having coffee with this guy and laughing at all his lame jokes. We ended up chatting for two hours then he excused himself to go back to the office.

“I hope I’ll see you soon.” He said after saving my number on his phone.

We ended up meeting again the following day after work and it became a routine. We’d grab a coffee, chat for several hours then head home. It was refreshing, I must admit. Dan made me feel special but I was still cautious about having feelings for him too soon.

Shortly after meeting Dan, I attended a friend’s house warming party where I met Brian. No one knew that I was seeing someone so my friend introduced me to him and we also hit it off at the beginning. Like Dan, Brian also paid close attention to me. I don’t know whether it was my past relationship that made me feel as if I couldn’t be loved but the kind of attention I was getting made me feel special.



I gave him my number and we planned a date for the following weekend. Since he didn’t work in town, it was easy for me to see Dan during the week then meet with Brian on the weekends. My plan worked perfectly. For the next two months, I went on dates with two guys without any of them knowing it.

I started becoming unavailable for most of my family and friends’ events and they started suspecting something was going on.

“Are you dating again?” one of my colleagues at work asked.

“I’ve seen you with a certain guy. Is that the new catch?” another chimed in.

They were all aware of my brutal divorce and how it affected me so seeing me in a chirpier mood was pleasantly surprising for them.

“Umm… He’s just a guy I met. Nothing serious.”

“Well, you definitely look happier and you don’t even come for Friday happy hour with us anymore.”

“Oh. I’ll come this Friday.” I replied to brush off their insinuations.

After a few months of dating the two guys and getting to know them a bit better, I started feeling guilty about what I was doing. I’ve never been a cheater and though I wasn’t in a committed relationship with any of the guys, it still felt like I was cheating on them.



I wanted to come clean about the situation but then I knew I’d be back to square one and I was enjoying their attention. Both of them called me regularly, sent me sweet good morning and goodnight texts, and surprised me with gifts occasionally. It was hard to let go of that. However, one day, Dan saw a gift package and flowers in my kitchen and started suspecting that I was dating someone else. I decided that it was best to tell both of them the truth before someone got hurt.

Since I saw Dan more often than I saw Brian, it was a bit hard letting him know. We went out for coffee after work as usual and as we conversed, I dropped the bombshell.

“Dan, I have something to tell you.”

“Sure. You can tell me anything.”

“Promise you won’t be mad at me.”

“I can never be mad at you.”

“Well, I have been dating someone else.”

He went silent. That was the first time I ever saw him speechless and almost disappointed. Dan was a cheerful, social guy. He was the life of the party so when he went silent I knew he was deeply hurt. He barely said anything to me for the rest of the evening and we walked awkwardly to the parking lot where my Uber was waiting for me. I wasn’t hopeful that I would hear from him after that day.

I got home, showered, and changed into my lounge clothes then contemplated whether I should tell Brian about it. However, I figured that if we were to have a serious relationship, it shouldn’t be based on lies. I couldn’t wait for the weekend to tell him so I called him.

“Hey, babe. Have you reached home?”

Yes, I just took a shower. I wanted to tell you something.”

“Sure. You can tell me anything.”

The conversation felt eerily familiar and my stomach turned knowing what was about to happen.

“You know, when we met I was actually dating someone else.”



Just like before, he went silent but not for long.

“What do you mean?”

“I was seeing another guy.”

“So, you were cheating on me?”

“Well, we weren’t in a relationship and I was getting to know both of you.”

Unlike Dan, Brian was very vocal. He didn’t take the news very well and let me know exactly how he felt. I’m not proud of putting them in such a situation especially after being in a toxic relationship and knowing how it felt to be cheated on. I realized I wasn’t ready to get back on the dating scene and I took another break.

Drop Your Comments