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Couple on a date. Image from https://thyblackman.com/2011/10/23/black-women-their-relationships-with-men/

Couple on a date. Image from https://thyblackman.com/2011/10/23/black-women-their-relationships-with-men/

I Dated Two Men At The Same Time For Years Who Wanted To Marry Me

Jack was the soft spoken workaholic while James was the hopeless romantic. I couldn't choose.

Singlehood Series by Singlehood Series
November 11, 2022
in The Singlehood Series
Reading Time: 5 mins read
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When I got into a relationship with two men, I had no idea things would get to the point that both of them wanted to marry me. I know it’s a cliche but I had no intention of dating two men at the same time. It just happened. I liked both of them and I didn’t know who to choose. So, I dated them both. However, I wanted to break up with one when I made my choice. That day just never came and they ended up asking me to marry them.

I met Jack first. He came to our office for some outsourced services and we hit it off instantly. Jack was the perfect guy. He was easygoing, fun, intelligent, and hardworking. For the first months of our relationship, everything was peachy. The only problem I had with him was that he was a workaholic and hardly had time for intimate moments. I grew lonely and bored in the relationship but I didn’t want to break up with him.

I went on Tinder to keep myself busy and it worked for some time. Most guys I met there weren’t keen on meeting in person which was perfect for me. Jack also knew that I was on Tinder but I assured him I was just talking to people and making friends. However, I connected with James and he charmed his way into meeting me in person.

He was everything Jack wasn’t. He was charming, flirty, and most importantly, emotionally available. I eventually let him know that I was in a relationship and he didn’t seem to mind.

“I take it as a challenge to make you all mine.” He said after I asked him if he had a problem with me having a boyfriend.

Indeed, he played his cards right and I considered breaking up with Jack to date him. However, Jack suddenly started paying attention to me. He became more romantic and showered me with affection. The trip to Zanzibar was the icing on top of the cake. He planned a romantic getaway to Zanzibar on Valentine’s Day which made me put a pause on the breakup.

“What can I do to prove that I’m serious about you?” James asked me after I came back from vacation.

“Jack is really stepping up. I want to focus on our relationship.” I explained trying to break up with him.

He didn’t get the message or at least, he didn’t stop pursuing me. James remained in the picture but he was more like the emotional support best friend when Jack wasn’t paying attention to me. Sure enough, we were back to the same old thing within a few weeks. Jack was back to being a workaholic and James was there to lift me up.

I grew so used to the arrangement that I stopped feeling like I was cheating on Jack. My relationship with James started to feel like the real deal. I’d go on more dates with him than with Jack. At some point, it felt like I was now cheating on him with Jack. He wanted me to break up with him.

“I’ll do it,” I assured him.

“When?”

“Soon.”

I never broke up with him but I later lied to James that I had. I didn’t think things would get that serious. However, soon after I told him I had broken up with Jack, he took me to a hotel in Naivasha where he proposed to me. I was in shock and I can’t even remember whether I said yes or not. When I woke up the following day, I was engaged to him.

The engagement made me realize that this was serious. Jack was serious enough to want to marry me. It also made my choice easier. I was sure that Jack was the one and that I had to break up with James now. We came back to Nairobi and started planning how I was going to move in with him.

“I have paid for two months’ rent so I have to stay here for the next two months,” I told him.

It was a lie. I was just trying to buy time. Within those two months, I tried to break up with James in vain.

“What do you want? Do you want me to marry you?” He asked one day as we had dinner.

Before I could answer, he was on one knee. Once again, I was bamboozled and speechless. I finally managed to say yes. He put the ring on as everyone in the restaurant cheered. I managed to fake a smile but deep down inside, I was having mini heart attacks.

How was I going to get myself out of this mess? Who do I break up with and how do I explain the break-up? In a perfect world, I would have picked Jack to marry. He was exactly my type. However, James was more financially stable and I was sure I wouldn’t have to lift a finger for the rest of my life. I decided to stick with James and break up with Jack.

Jack didn’t take the break up well. He vowed to ruin my life and my relationship with James. However, I thought they were empty threats and brushed them off. Jack was soft-spoken and I didn’t think he had it in him to be confrontational. I was mistaken.

He showed up one day at my apartment when James was there. I refused to open it but he managed to shout everything he wanted to say.

“She was supposed to marry me. I proposed to her in Naivasha,” he said.

James just looked at me with a look of confusion and disappointment. Jack finally left after saying what he wanted to say and we were left alone in silence. James didn’t say much after that. He asked for his ring back, packed his things, and left. I sent him a lengthy text apologizing for the incident and explained that I wanted to marry him. He didn’t care about anything I had to say. He refused to pick up my calls or texts and no matter how hard I tried to contact him, he never replied.

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Singlehood Series

Singlehood Series

The singlehood series is a collection of real-life stories and opinions from different people. It looks at the current world of dating around the world and the experiences that people have gone through.

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