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The Singlehood Series: I Went On A Date With A Yes Man

Singlehood Series by Singlehood Series
28 February 2022
in The Singlehood Series
Reading Time: 5 mins read
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Men have always gone out of their way to impress me. I enjoy it but sometimes it gets annoying especially when you meet a yes man.

Damian and I had been friends since our high school days. I never thought anything would happen between us but he always tried to ask me out. After some time, he accepted that we couldn’t be anything more than friends. One of the main reasons I wasn’t attracted to Damian was because he was a yes man. He would do anything I said without questioning it. However, he wasn’t like that with anyone else, even the girls he dated. He just did it with me which made it even more annoying and weird. Nonetheless, he was a great friend that I could rely on.

We stayed friends throughout university until we became grown adults with jobs and cars. Our lives were going great. We were both in relationships, had good jobs, and could afford small luxuries. This was until everything came crashing down. I found out that my boyfriend of two years whom I had planned to start a family was cheating on me with one of his colleagues. This broke my spirit and I even quit my job. As always, Damian was there to comfort me.

“I’m so sorry, Clara. You don’t deserve this.” He said as we sipped wine in my apartment.

“I don’t know what to do. I had planned my whole life with this man.”

“You know, I would never do anything like that to you.”

“What are you trying to say?” I asked wiping my tears.

“I’m saying if you give me a chance I’ll treat you like the queen you are.”

“Dam, you have a girlfriend and I’m not about to be the side chick.”

“I’ll leave her. Winnie and I have been having problems anyway. She says I’m obsessed with you. So, why don’t I just be with you?”

“This sounds like a bad idea, though.”

I was right. Most of the time, nothing good ever comes from dating someone you’ve been friends with for a long time. However, I was in a vulnerable state and was desperate for affection. Damian knew how to give affection so I gave in and agreed to go on a date with him. it was like I had told him he had won a million dollars.

“I promise you won’t regret it. In fact, who knows? You might end up marrying me.”

“Calm down. Let’s get through the first date.”

Despite knowing that he was a yes man, I still gave him a chance hoping that I’d have a better dating experience. Maybe it wasn’t so bad dating a yes man. Besides, all my friends rooted for him so they must see something in him.

It took about a month to get over my heartbreak and also give Damian time to end his relationship. After a month, we reconnected.

“Hi, gorgeous.” He said when I answered the phone.

“Hi, Dam. How are you doing?”

“Better than ever. I’m single now. So how about that date?”

“I’m ready when you are.”

“Okay. This Saturday.”

“Okay.”

Since I hadn’t seen or talked to him in a month, I actually missed him. I was excited about the date. It felt as if I was going on a date with my soulmate. After all, Damian was the one person who knew me inside and outside so I knew the date would go well.

I ravaged through my closet to find the perfect dress that would leave a good impression on him. He might have been a yes man but he was still a man and I knew the type of woman he liked. I settled for a figure-hugging ruched dress and a pair of strappy heels.

He came to pick me up and we made our way to the restaurant. It was a new place that I hadn’t been and from the looks of things he hadn’t been there before. As soon as we sat down, he started bombarding me with questions.

“Are you good?”

Yes”

“Do you like the place?”

“Yea. It’s fine.”

“What are you eating?”

“I haven’t even seen the menu.”

“Okay. Let’s wait.”

I immediately started regretting going on a date with him. When the waiter came to take our order, he chose the same things I did.

“Don’t you want to try something different?” I asked.

“No, I want exactly what you’re having.”

He even ordered the same cocktail I was having. That was only the beginning of a long, weird night. I started getting attention from a group of men seated next to us. Damian would nod and laugh anytime they complimented me. It got so uncomfortable that I suggested we move. Of course, he said yes.

“I thought you were having fun. Those men think you’re beautiful.”

“So? I get that all the time but the way you reacted was very inappropriate.”

“Okay, I’m sorry. I’ll do better.”

At that point, I had had enough and was ready to leave but I had to share my thoughts with Damian.

“Babe, you know I love you. You’ve been my friend since I was 18 and I couldn’t have asked for a better friend. But you need to stop being a yes man. It’s annoying.”

“A yes man? I’m not a yes man.”

That was the first time he had ever said anything that didn’t coordinate with what I said.

“You are, at least with me. Everybody sees it and they think it’s cute but I don’t like it. I hoped that this date would be different and you’d treat me like any other person but it’s clear that you’re too infatuated. I don’t think we can work as a couple.”

We remained friends but I started seeing a different side of Damian. He became colder and we weren’t as close as we were before. Even though I lost a close friend, I’m glad I put a stop to his creepy behaviour before it went too far.

More stories in The Singlehood Series:

My Cousin Stole Her Best Friend’s Fiancé

My Best Friend Fell For Me And Now Our Relationship Is Ruined

She Slept With Her Best Friend’s Boyfriend By Mistake

When The Alpha Male Turns Out To Be A Mama’s Boy

When You Become His Permanent Side Chick

The Girl Who Doesn’t Take No For An Answer

He Was Not Her Type But She Decided To Give Him A Chance – What Could Go Wrong?

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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 around the world and the experiences that people have gone through.

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