I Have A Date With Kylie Jenner
- Alan Tobin
- Nov 17, 2025
- 3 min read
Updated: Nov 19, 2025
Attention Readers: What follows is a work of satire.
Well, it’s official. Hollyweird’s most unlikely couple have called it quits.
Yup. Actor Timothee Chalamet and reality star Kylie Jenner are yesterday-ville. You know it’s true, because I read it on my cell phone.
Knowing this was the perfect opportunity to make my move, I fired off an email to Kylie today. So what, if she’s 40 years younger than me and I’m married. It blew my mind when she emailed me back.
"I will go on a date with you Mr. Al. Just let me know when and where. You sound like an interesting man."
In the end things didn't work out so well with Timothee. I think it was the French side of him that made him so angry. All I said to him was that I didn't care for that biopic he made about Bob Dylan. You know the one. I think it's called "A Complete Unknown." I also told him Bob Dylan's music sucked. And that was it. Timothee didn't want to have anything to do with me after that."
After I got her email, Kylie's agent made arrangements for us to talk on the phone. She told me she talked to P Diddy and Diddy vouched for my character. And guess what? Kylie and I have a date for Saturday night.
I told Kylie I normally wouldn’t go out with a woman on the rebound, but in her case, I’ll make an exception, especially if she wears that backless top with the thin gold chains.
Kylie’s my crush and this is the perfect opportunity for me to revisit my teenage years.
Kylie is a gazillionaire socialite with her own fashion and makeup lines. I have a couple of thousand in my checking account and a room at Budget Suites. Guess that makes me a thousand-aire. You know what they say. Opposites attract.
Oh, and did I mention I have half a circumcision. I think she’ll find that interesting when we consummate our date.
Kylie’s dad is Bruce Jenner, who is now Caitlyn Jenner. I told her it would be really cool if she wanted to have Caitlyn serve as our chaperone. I’m kind of old fashioned that way and like the idea of a chaperone.
I want to ask Caitlyn about her SRS, because I’m thinking about undergoing sexual reassignment surgery myself. You got to have an open mind about these things. Not that I’m confused or anything.
Kylie said no problem. So, I think we’re cool. I want to ask Caitlyn about when she won the decathlon in the 1976 Summer Olympics.
I asked Kylie how she feels about dating an older man. She said she has a thing for liver spots.
Kylie seems very classy and down to earth. I think I’ll take her to McDonald’s. If she prefers Chinese I'll take her to Panda Express. That's what my buddy, Ramon De Leon recommends.

I also asked Kylie if she could bring her sister, Kendall on the date. That way I could say I bedded both the Jenner sisters at once. Not that I'm a pig or anything. Kylie said that would be fine.
I have the deepest admiration for Kylie's family. Her peeps have done so much to elevate art and culture in the new age.
It's been years since "Keeping Up With The Kardashians" aired on the E! Network. It was one of the longest running reality TV series in U.S. history. I loved that show. I should have been the executive producer of the series instead of Ryan Seacrest.
The show highlighted the lives of Kim, Kourtney and Khloe Kardashian. The show aired from 2007 to 2021. Kylie and Kendall were on the show too. Kylie was featured in 193 episodes. Kendall in 241 episodes. I loved the story lines. They were fabricated. Just like this story.
We were all so damn lucky back then to have "Keeping Up With The Kardashians." The show ushered in a new age of enlightenment. It made us all better Americans. I even got me a Kim Kardashian mask that I wore when I watched the show. And when Kanye West married Kim Kardashian I knew for sure America was a great country.
Now don't be calling TMZ with the inside skinny on Kylie and I. We're trying to keep our relationship quiet for the time being.







If Kylie Jenner is a social media creation, then Mr. Al is an anachronism.
Kylie Jenner is a creation of a social media world.
What are you going to get Kylie for Kristmad?
Mr. Al are you going to spend Thanksgiving with Kylie?
Mr. Al you have sexual charisma.