The Singlehood Series: She Sued Her Boyfriend For Failing To Propose After Dating For 8 Years

Couple in court. Image from

When I finished campus, I had big dreams – get a good job, move out, and marry the love of my life. Jackson and I had been dating since our third year of university. He was charming and swept the little village girl in me right off her feet. I never imagined that we would end up in court because he failed to propose to me.

We were quite young when we first met. I was barely 20 years old and he was 21 but we were both ambitious and shared similar life goals. However, he didn’t seem as serious with our relationship as he was with his other goals. During our courtship, he would flirt with other women and we broke up on numerous occasions due to his lack of commitment.

Nonetheless, we carried on our relationship until we cleared university and graduated. After 4 years of dating, I got pregnant. Jack was adamant about not keeping the child despite both of us having stable jobs. I kept it regardless of his objection and nine months later, I gave birth to a beautiful baby girl.

“Babe, when are we going to make things official?” I asked him for the millionth time.

“What do you mean?” he asked as if he was clueless about what I meant.

“We’re basically a family now. I want you to marry me.” I didn’t mince my words.

At that point, I needed to make it clear that I still wanted the happily-ever-after since he seemed more relaxed than ever to propose to me. Years went by and our daughter grew into a bubbly angel as I waited for my proposal. Jack seemed to get distant instead of falling deeper in love with me. However, I had invested too much of my time in our relationship to throw it all away just because he was bored.

I tried everything to go back to the girl he fell in love with in university and I did. I was quite hardworking and headstrong so it was easy for me to hit the gym and get in shape. My body looked even better than it did when I was 18. I felt good about myself again and it showed. Men started taking notice of me again and some even made a move on me. But I rejected them all while holding on to the dream that the love of my life would finally make me his wife.

Jack appreciated the transformation as well. He became more affectionate and started showering me with his attention. Things were going well and for a moment, there was a light at the end of the tunnel. It was nearly 8 years of dating now and the proposal felt like an obligation more than a romantic gesture.

“Do you think he’ll propose?” I asked my best friend who was organizing my birthday party.

“He better. Do you want me to give him a hint?”

“No, I think he’s gotten the point now. He’s not going anywhere and neither am I.” We both laughed but it wasn’t really a joke.

Couple in court. Image from

The big day finally came and I had jitters like it was my wedding day. My best friend had organized an intimate picnic event that simply looked magical. Jack was in good spirits, entertaining the guests, and parading me around to everyone. It had been a long while since he showed me that much affection. Somehow, I knew he was going to propose that day. However, the day turned to night and nothing had happened. Some guests started leaving and Jack didn’t seem like he was in a rush to pop the question.

The day was growing old when he finally stood to make a speech.

“Babe, I’ve watched you go from a sweet, naïve college girl to a boss and the mother of my child. I couldn’t be happier that I was with you for that journey. Today, you turned a year older and you keep getting finer with age. May you continue to prosper and I hope that I can be a part of it all. With that said…” he paused as he felt the pocket of his pants.

“This is it, babe.” My best friend whispered.

He pulled out a black velvet box but it looked too large for a ring. I watched so many romantic comedies that I became paranoid about being bamboozled. I still kept my hopes up and prayed it was a ring. It wasn’t. He gifted me a necklace with an emerald – our daughter’s birthstone. I was fed up with waiting for him to propose. Every year, the chances only became slimmer and I couldn’t take it anymore. Everyone was just as confused as I was that day but no one said anything.

We all went our separate ways and Jack left with his friends to conclude the night. I got to the house, packed all his clothes in a suitcase, and placed them by the door. I then sent him a message letting him know that he should pick up his things because it was over between us. In my emotional state, I contacted a lawyer friend to ask if it was possible to take any action if someone failed to propose.

“Yes,” she said after explaining lots of legal jargon I really didn’t care for.

“Great. I’ll come to see you at your office tomorrow.” I said then hang up.

Jack hadn’t returned home by the time I woke up to go to the lawyer’s office. We agreed to take the matter to court and after a few weeks, we had our day in court. It was a pure comedy show for the audience but I was an emotional wreck. I could hear the people whisper and others chuckle every time I explained what I had been through. Eventually, the case didn’t go through but it hit Jack that he had wasted my time.

Though he didn’t propose, he apologized for taking me for a ride. We decided to go for counselling for the sake of our child and after months of mediation, I was able to forgive him. We broke up but are now great co-parents to our daughter. I’m still waiting for my Mr. Right to come around but in the meantime, I’m enjoying the single life quite a lot.

This story is inspired by a story on Foxnews

More stories in The Singlehood Series:

My Wedding Proposal That Went Horribly Wrong

After Years Of Dating He Broke Up With Me Because According To His Family, I Was From The Wrong Tribe When It Was Time To Get Married!

For Years She Lived In Blissful Ignorance But One Day She Found Out That Her Husband Wasn’t Who She Thought He Was

When Mr. Right Just Wants To Keep It Casual…Friends With Benefits

He Lied About His Army Missions And I Found Out In A Hilarious Yet Heartbreaking Way

He Introduced Me To His Mother But Nobody Told Me My Boyfriend Had A Girlfriend And A 7-Year-Old Son

She Kept Asking Him To Introduce Her To His Mother And When He Did She Was Shocked At Who It Was!

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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