The Singlehood Series: I Confessed To Stalking Her On The First Date

Couple on an awkward date. Image from

First dates have never been my thing. I always fumble and say the wrong thing which may explain why I hardly ever get a second date. This time, it was no different. I decided to shoot my shot with my long-time online crush, Maya, who I admittedly had been stalking for years. If you saw her you’d understand why. However, my crush on her started long before the age of Instagram. It started on Facebook just after high school.

We shared several mutual friends so I took an interest in her profile and it never disappointed me. Even back then, she was just as pretty and fashionable as she is today. Her pictures were always on point and her personality just radiated through the screen. I was really into her. Every time I met one of our mutual friends, I always asked about her but never had the guts to reach out to her.

I think the only time I interacted with her directly was once when I wished her a happy birthday. Still, I obsessed over her year in year out. Thinking back at it, it was creepy. I spent hours scrolling through her posts and laughing as if she was talking to me. my interest soon escalated to stalking. A day wouldn’t go by without me checking her social media accounts. I knew where she lived, which restaurants she liked going to and I befriended some of her girlfriends. Sometimes, I’d attend the same event she was attending just to get a glimpse of her.

This went on for a few years until I mastered the courage to ask her out. She had hinted that she was in the market so I thought it was the perfect timing. I was still aware of the fact that it would not be easy to woo her so I eased my way into her life.

“You look gorgeous,” I commented in one of her pictures which she replied with heart emojis.

I became a frequent commenter to the point that she would DM to check up on me. We became really good friends and she’d occasionally invite me to events she was attending. Of course, I never showed up. After stalking her for years, I wasn’t going to just pop in on her. I wanted our first meeting to be unforgettable and it surely was.

“I thought I’d see you at the event last night.” She DM’d me.

“Sorry, I couldn’t make it. Work stuff.”

“It’s okay. I understand but it feels like you’re avoiding me. This is the fifth time you haven’t shown up when you said you would.”

“I know. I’m sorry. Let me make it up to you.”



I knew she couldn’t turn down cocktails after work.

“Okay. Tomorrow?”

“Sure. I’ll text you the place.”

“Great. I can’t wait to meet you.”

“Me too.”

Since I had already seen her a few times before, I wasn’t as nervous about our first date. It’s like I had known her for years. I knew almost everything she liked from movies to food so I wasn’t scared of messing up during the date. Maybe I shouldn’t have been overconfident because I somehow felt too comfortable with her.

Couple on an awkward date. Image from

We met at a café in town. She showed up almost as soon as I arrived looking like a dime. I waved at her and she spotted me. I could tell she was excited to see me because she approached me with the biggest smile I had ever seen. You can’t even imagine how excited I was that I finally got to know her on a personal level after all those years.


“Yes. You’re even more beautiful in person.” I said as she settled in her seat.

The waiter came to take our orders and I decided to show her just how much I knew her. Bad idea.

“Ah, I’ll have an Old Fashioned and she’ll have a Sangria.”

As soon as I ordered, she gave me a weird look.

“Did you know that’s my favourite drink?”

“Yea, that’s all you drink whenever you go out.”

“I see someone has been taking notes.”

“Yea. I’ve been stalking you for years.”

At the moment, I thought it was a cute thing to say but I soon found out it wasn’t. She stared at me as if I had said the worst thing she’s ever heard. We didn’t speak for a whole 5 minutes until I decided to break the ice.

“I’m sorry. Did I say something wrong?” I asked.

“What did you mean by you’ve been stalking me for years.”

“Well, you know, I’ve been attracted to you since I first saw you.”

“But I thought you just started following me a few months ago.”

I had no response. I had dug myself into a hole I couldn’t get out of. No matter how much I tried to change the topic, she just couldn’t let it go. The rest of the date was a disaster but I commend her for sitting through it all.

“I need to go.”

“Okay. Let me call you an Uber.”

“No need. I already called one.”

She probably didn’t want me to know where she lived which was smart of her. I escorted her to the Uber and that was the last time I heard from her. Some of our mutual friends informed me that she had been asking about me and that she knows I’ve known her for years. I guess it was a matter of time since she found out the truth but maybe things would have been a bit better had she found out a bit later.

I’m still trying to pursue her and I don’t think I’ll be at peace until I know how things would be like after the first date. At least, I’m not blocked so it could be a good sign that she’s not as upset about the whole situation. However, I don’t know how we will move past the whole stalking issue.

More stories in The Singlehood Series:

I Had Three Crazy Tinder Experiences Which Forced Me To Delete The App

He Went On A Blind Date And Had Dinner With The Wrong Girl

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

The Time Mr. Nice Guy Turned Into A Stalker

My Date Offered Me Money So I Could Leave

He Asked Me Out On A Brunch Date But Took Me To Church Instead

When He Lies To You That He Is Broke, Then You Find Out He Is Treating Himself To Expensive Spa Dates

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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