The Singlehood Series: I Got Out Of The Friendzone And Dated My Best Friend For One Month

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Nancy and I had been best friends since we met at university. I was in the friendzone for years. For some reason, I never made a move on her and she assumed I simply wanted to be her friend. However, I’ve had a crush on her since the day we met. There were times where we almost got intimate but I always got cold feet and then she got into a serious relationship and it seemed like my chances of ever being with her were next to none. Then she broke up with her boyfriend.

As a caring guy in the friendzone, I was there for her as she got over the breakup. I took her for ice-cream dates, watched romantic movies with her, and even slept over at her place several times. On one of the nights, I got a bottle of wine and we drank the whole night away talking about our university days. This was the day that I got to kiss her. She felt warm and her lips were so soft. Even after our relationship ended, I still think about that day.

“You know I’ve liked you since that day we met at the cafeteria,” I said after kissing her.

“Really? Why didn’t you do anything about it?”

“Honestly, I thought you’re way out of my league. You’re stunning, smart, popular… Every guy wanted you.”

She blushed then leaned in for another kiss.

That was the beginning of a magical but short relationship. Since we had been friends for so long, everything came naturally. There were no awkward first dates. We knew exactly what the other person liked which made it easy to get everything right. We rarely fought or disagreed on anything. The best part was that all our friends got along so there was no resistance on any side. In fact, they were quite excited when we went public with our relationship.

“It’s about time you got out of the friendzone.” One of them commented.

I thought things were going well but I noticed Nancy started to drift away from me. Within a month of dating, she seemed to be getting bored of my company. She started rain checking more and even when we hang out, her mind was somewhere else. I knew that she liked a bit of drama but she had told me that she was over those kinds of relationships and wanted something more consistent. Besides, I was the least dramatic person I knew.

For the next month, whatever I did always felt like it wasn’t good enough. She was completely over the relationship and I tried to hold on to it. The old things didn’t impress her anymore. She started acting like I was in the friend zone again. Apart from being a bit of a drama queen, Nancy was also high maintenance both financially and emotionally. This was one of the reasons I avoided a relationship with her. Her boyfriends spoilt her with gifts and grand gestures which she was used to since I met her. I wasn’t as financially able as her past boyfriends but I tried my best and catered to her emotional needs.

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The ice-cream and coffee dates became old really quick and Nancy made it known she was getting bored. She took up offers from other guys to go out of time with them. Though most times, they were her work colleagues going on a work trip, it rubbed me the wrong way. I would have to save for months to take her to some of the places she stayed at during those trips.

“Nancy is thinking of seeing other people.” One of our mutual friends told me.

“I’ve done everything I can for her.”

“I know. But it’s Nancy. She loves the high life. She wants expensive shoes and romantic dates. It was only a matter of time.”

“I’m not giving up on her. I finally got my dream girl and I’ll not lose her over material things. I know she can look past it if I show her how happy I make her.”

She was happy. Everyone could see it – even her parents. They loved me and supported our relationship. When they found out Nancy wanted to end the relationship, they were willing to help me win her over. However, I had to do it myself. If I tried to impress her with material things, then I’d be like all the guys she dated before. I had to be different – or so I thought.

I was greatly mistaken. It didn’t take long for Nancy to reach her limit and call it quits. To make it worse, she broke up with me over the phone since she was out of town.

“You know I love you and you’ll always be my best friend…” she started.

“Are you breaking up with me?” I asked.

“I see how hard you work to make me happy and I don’t want you to break your back for me.”

“Have you found someone else?”

“There’s this guy at work…”

I didn’t let her finish. It still didn’t make sense of how I got out of the friend zone with the most beautiful woman and messed things up. Though we remained friends, we weren’t as close as we were before. Her new man seemed to be exactly what she liked and needed. He took her on trips and surprised her with romantic gifts. I never met him but our mutual friends told me he’s a great man.

After a few months of dating, Nancy got engaged to the man at an exclusive resort in the Maasai Mara. I was happy that she had settled down with someone who made her happy. However, on the other hand, I felt betrayed. She was my best friend and was supposed to stick by me no matter what just like I had stuck by her for all those years. I guess loyalty isn’t two-way traffic and what you give isn’t always what you get. We haven’t talked much since she got engaged and our friendship seems like it’s also going down the drain. Regardless, I’m happy I got a chance to get out of the friendzone and date her.

More stories on The Singlehood Series:

She Found Out Her Best Friend Was Dating Her Ex-Boyfriend

She Broke Up With Me Because Of A Sponsor

I Found Out My Boyfriend Of 5 Years Was Married When He Sent Me The Wrong Text By Mistake

My Crazy Ex Threatened To Beat Me Up After I Broke Up With Her

When He Sends You Mixed Signals – The What Are We Question

The Singlehood Series: How I Bumped Into His Girlfriend At The Movies And Ended Up Watching The Movie Alone

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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