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The Singlehood Series: He Bragged About Sleeping With Another Woman After We Went On A Date

Woman frustrated by man. Image from https://www.guystuffcounseling.com/counseling-men-blog/help-theres-constant-arguing-in-our-relationship

The Singlehood Series: He Bragged About Sleeping With Another Woman After We Went On A Date

I should have known that Henry was only playing with my emotions.

Singlehood Series by Singlehood Series
10 June 2025
in The Singlehood Series
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When I saw a notification from Henry on my phone, my heart nearly stopped. It had been a month since we last went on a date and two weeks since we last talked. I had made a promise to myself that I wouldn’t give in to his requests so easily. He had kept me waiting for a whole month, so I also wanted to give him a taste of his own medicine. Well, I didn’t stick to the plan. I replied almost immediately and he asked me on a date.

“You’ve been so quiet,” he said.

“Me? You kept cancelling plans with me.”

“I’ve been busy.”

“That’s what you always say.”

“Do you want to go on a date with me today?”

I wanted to turn him down but I found myself accepting the invite.

“What time?” I asked.

“Around 7 pm. I have a few errands to run, then I’ll be free.”

“Okay. Will you come for me?”

“I’m not going to be on that side of town.”

I knew he would refuse to come and pick me up but I just wanted to test the waters and see if he even cared a little about me. He didn’t.

I waited as the hours went by so I could go and meet him. At around 6, I messaged him just to confirm if we were still meeting.

“Hey, are you done with your errands?” I asked but the text went unanswered.

By that time, I had almost no faith in Henry. I knew he could cancel our plans any minute, so I had accepted that we may or may not meet.

Thirty minutes later, he replied, “Sorry, things got hectic.”

“Are we meeting or not?” I asked coldly.

“I’m coming to pick you up in an hour.”

I was happily surprised but an hour went by and I didn’t hear from Henry. I didn’t call or text him again. At around 9 pm, he messaged me.

“Can you get an Uber? I’m sending you the location.”

He sent the location of a park & chill spot. That wasn’t what I had in mind for a date but I was happy just to hang out with him. I got ready and headed to the place.

When I got there, he came to pick me up at the gate and he was in a great mood. After exchanging pleasantries, we walked to his car as he admired my physique.

“You look nice.” he said as soon as we got in his car.

“Thanks,” I answered, smiling.

Things were good at first. Though it wasn’t my idea of a date, I was having fun. We were drinking, listening to music and talking about life.

I started thinking that Henry had finally seen my worth and he was going to choose me as his girlfriend. He was doing everything right from refilling my cup when it was empty to complimenting me.

I had always wanted to be Henry’s girlfriend ever since we met many years ago. However, it never happened. I ended up dating his friend for two years and when we broke up, I lost touch with all of them.

Last year, I got a message from Henry and we rekindled our friendship. When we met, he let me know that he wanted to have a relationship with me. I was excited because I wanted the same thing, but till now, nothing has happened.

He rarely took me out on a date. I can count the number of times we have gone on a real date. He mostly asked me to go to his place or meet at a club. I was ready to call it quits before he contacted me that day.

“Today is the last chance,” I told myself as I got ready to meet him.

It seemed the universe had whispered something to him because he was being extra romantic.

However, things changed when Henry got a little tipsy. The egocentric, selfish side of him started coming out. I had seen it many times so I wasn’t surprised.

“You know, you’re just pretty. You don’t have anything else going on for yourself,” he said.

I stayed quiet since I didn’t want to argue with him. He kept provoking me but I kept my cool. However, I lost it after the constant provocation.

Henry knew I had one insecurity – being cheated on. I could put up with anything but being cheated on was a deal breaker for me.

“There’s a girl who came over to my place last week,” he said casually.

“What?” I replied, trying to stay calm but my eyes were seeing red.

Henry smirked. He knew he had triggered me, which was exactly what he wanted. Normally, I wouldn’t care since Henry and I weren’t officially dating. However, the last time we went on a date, he made me think that he was ready to settle down.

“She got so drunk, she removed her clothes and started dancing all over the house,” he added.

I could feel my face getting hot but there wasn’t much I could do. Henry continued talking but all I could see was his lips moving.

“Why are you telling me about this?” I asked.

He didn’t answer. He just kept talking about the epic night he had with the other girl.

At that point, it was very clear that he not only didn’t want anything serious with me but also he had no respect for me.

He knew how I felt about him and how I felt about being cheated on yet he still bragged about sleeping with another woman. I felt so embarrassed and degraded.

The worst part was that it was so late that I couldn’t go home. I ended up going home with Henry and we were intimate.

He ended up ghosting me again and we haven’t spoken to each other since then. I was heartbroken but I moved on. If he ever contacts me again, I will not even consider meeting with him.

Check out

I’ve Been Secretly Seeing My Ex For Years

I Decided To Date Like A Man And I Hated It

Her Boyfriend Had A Toxic Trait That She Discovered After Getting Pregnant

He Ghosted Me Then Asked Me Out Again But I Have Doubts

My Blind Date Turned Out To Be A Guy I Had Ghosted

He Asked Me To Go On A Trip With Him But Ghosted Me On The Day We Were Supposed To Leave

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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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