The Singlehood Series: He Took Me Out On A Valentine’s Date Then Broke Up With Me

Couple taking. Image from

Derrick and I never had a perfect relationship. However, we were good at working things out every time it felt like the relationship was coming to an end. I thought it was the same this past Valentine’s Day. We had a big fight the previous week and he didn’t talk to me for a few days. Then, out of the blue, he asked me out on Valentine’s Day.

I was surprised but excited since I didn’t expect him to do anything for me on that day. Nonetheless, I had prepared an outfit just in case he had a change of heart, or I made plans with my single girlfriends. On Friday night, I got a text from him reading:

“Hey babe, I’m sorry I’ve been so quiet but I miss you so much. Let’s not fight. I want to take you out on Valentine’s Date.”

I won’t lie, I got butterflies in my stomach. For some reason, it felt like we were starting afresh. Derrick and I had also never spent Valentine’s Day together despite being together for years. We were always fighting around that time of the month and never got a chance to go on a date. Due to all the excitement, nothing seemed suspicious and I was under the impression that he was just as happy as I was to pick up where we had left off. The following day, I gave him a call just to confirm that it wasn’t a random drunk text and that he really wanted to go on a date.

“Hey, hun.” He answered on the other end.

“Hey baby, I got your text last night.”

He laughed and I held my breath ready for the bad news.

“And?” he replied.

“Are you serious?”

“Yes, girl! I want to take you out. Do you have a dress or do you need to buy one?”

“I have one.”

“Good. I’ll come to pick you up around 5 p.m. Be ready.” He said then hang up.

I couldn’t stop smiling after that phone call. One of the main reasons we argued a lot was because we hardly went out. In fact, our last fight was because he said he didn’t have plans for Valentine’s Day and wanted “to chill”. It seemed like he was finally making an effort to do things for me. He even offered to buy me a dress. This was a very different version of Derrick that I had never seen before. I liked it and so did my friends. As soon as I told them he had asked me out on a date, they all had the same response.

“It’s about time.” One said.

“He’s finally acting like your boyfriend.” The other said.

“He better propose next.” My best friend chimed in.

None of us thought anything suspicious was about to happen. For some reason, I never expected Derrick to be a vengeful or petty person like that.

Valentine’s Day came and I was in good spirits the whole day. Everyone seemed to be having a good day as well. I scrolled through Instagram, smiling at all the happy couples posting about each other then decided to give Derrick a call. It didn’t go through the first time, or the second or the third. In fact, I didn’t talk to him the whole day until around 4 p.m. when he called to ask if I was ready.

“Have you not seen my missed calls?” I asked a bit agitated.

“I was busy, babe. Relax. I hope you’re ready. I’m on my way.”

“How was I supposed to get ready when I couldn’t get a hold of you the whole day?”

“Don’t start your petty drama, Ruth. Just get ready. I’m coming.”

Once again, he hung up abruptly and I was left talking to myself. Nonetheless, I wasn’t going to let his attitude ruin my mood. I started getting ready and within an hour I went from looking like a couch potato to looking like a model. If my sparkling red dress wasn’t going to work magic tonight, I didn’t know what would. This was the type of dress you wear to either make your ex jealous or your boyfriend weak. Since I wasn’t sure about my relationship status, I was hoping that tonight would mark the beginning of something new and better.

At around 5.30 pm, Derrick alerted me that he was outside my door and as I stepped out, I saw a sharply dressed man standing at my door. I had never seen him in a suit before. He worked in the IT department so his daily uniform was a graphic t-shirt and blue jeans. Honestly, I envied that he didn’t have the pressure to dress up for work but at times, I wished that he would. He did that day and he looked irresistible.

“Wow. Look at you,” I said as I stood at the door.

“Look at you too. You look gorgeous.”

“Thanks. We’re gonna have a good night.” I answered with a smile.

We made our way to his car then drove towards Westlands. He still hadn’t said where we were going but I trusted him to pull it off. I sat back, controlled the playlist, and jammed as he drove. We then stopped at Park Inn. This was where we first met during a wedding reception for one of our mutual friends. We had never gone back after that day and it took me by surprise that he actually remembered.

“We’re here.” He said coming out.

He opened my door and helped me out then we walked hand in hand to the entrance.

“I can’t believe it,” I said almost in a whisper.

“Why? You thought I don’t care.”

“I’m getting emotional. Are you going to propose?”

I had to ask because things were going too perfectly.

“Just wait and see.” He replied with a cheeky smile.

We were escorted to a reserved table with a beautiful view of the city and just as I was about to settle down, he broke the news.

“I’m breaking up with you.” He said looking me straight in the eyes.

It took me a minute to process what just happened. A few minutes ago I thought he was going to propose and now he was breaking up with me. We hadn’t even sat down.

“I can’t do this anymore, Ruth. You are too controlling and uptight. I’ve tried to put up with you all these years hoping you’ll loosen up but I’ve had enough.”

Couple arguing on a date. Image from

“Put up with me?” I responded. “I’ve put up with your boring, awkward self all these years. I mean, look at me. I’ve dated CEOs and business moguls only to end up with an IT guy. You should feel lucky you spent three years with me. Those were the best years you’ll ever have in your life.”

I didn’t wait for his response. I turned around and made an exit as people stared at me. At that point, I didn’t care much. I had gone through a lot of humiliation dating that guy. While I waited for my Uber to arrive, Derrick walked right past me and got in his car without saying a word. The least he could have done was wait for my Uber to come. Anyway, that was the kind of guy I had wasted three years dating. I’m just glad it’s over.

More stories in The Singlehood Series:

I Went On A Date With My Instagram Stalker Without Knowing It

I Was Cooking For My Boyfriend During Lockdown And He Was Eating My Food With Another Woman

The Date With The One That Didn’t Work Out

She Sued Her Boyfriend For Failing To Propose After Dating For 8 Years

The Singlehood Series: I Was Blind Dating A Guy On Phone Who Said We Met At The Club, Only To Find Out He Was My Uber Driver

Single Lady In Nairobi: When I Got Dumped After Valentines

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The singlehood series is a collection of real-life stories and opinions from different people. It looks at the current world of dating in Kenya and experiences that people have gone through. The views and opinions expressed here are those of the contributors and do not necessarily represent or reflect the views of