Omaha Boys Imagines {Discontinued}

Gilinsky (Request)

This one was requested by the babe with the name Regan🌷

*Jacks POV*

"Well here goes nothing" I said to myself walking up to my gorgeous crush Regan. I have liked her for about 3 months now but never had the courage to talk to her. Plus she just broke up with her horrible boyfriend Ben. She shouldn't have been treated the way he treated her, cheating on her all the time, sleeping around with other girls, lying to her, just being an all around dick. She deserved way better, and I am bound to be better to her, if I even have the chance. I walked up with a dozen roses in her favorite color, blue. "Alright let's do this"

*Regan's POV*

I was finishing up talking to my best friend about how I broke up with Ben. Damn, he was an asshole. "Don't worry you will find someone way better then Ben. I promise, I think he's coming right now!" She said with excitement. "What the fu-" I said then turned around to something I didn't expect.

"Regan, I have liked you for a while now, and I was wondering if you would like to go on a date with me Saturday?" Jack Gilinsky, the most adorable guy in school said, walking up to me and handing me flowers. "Oh my god, Jack, I'd love to!" I said hugging him.

"Okay here's my number I'll text you the details tonight" he said handing me a piece of paper with his number on it. "Okay, thanks for the flowers Jack, that was really sweet!" I said blushing, seeing everyone look at the scene. "Anything for such a beautiful girl" Jack said walking away, winking at me.

"Did that just happen?!" I asked my friend in shock. "Yes! Oh my god that was so adorable I can't believe that!" She said with excitement. "In my favorite color to!" I said looking at the baby blue roses smelling them. I headed home and put the roses in a vase with water and put them in my room, took a picture and put it on Twitter. 'Such a sweet surprise from a sweet boy @jackgilinsky looking forward to our date Saturday! 😘😘😘😘'

*Jacks POV*

SCORE!!!!! I got the girl of my dreams to go on a date with me.! I drove home and then when I got in my room my phone went off, I was hoping it was Regan. It was a Twitter but it was a notification from her! 'Such a sweet surprise from a sweet boy @jackgilinsky looking forward to our date Saturday 😘😘😘😘' I was filled with excitement when I finished reading the tweet. Now, to plan this date...

*Regan's POV*

I should probably find more out about this date, so I'm gonna text Jack.

R: hey, it's Regan
J: oh hello beautiful, so here's the deal, be ready by 5 that's when I'll pick you up, dress casual, make a music playlist and don't ask questions. But real quick, favorite snack and favorite drink.?
R: haha okay? I like fruit well, anything really, and any soda. I don't really have favorite anything,..
J: okay. Well remember I'm picking you up at 5!
R: hahah okay Jack I'll be ready ☺️
J: okay get some rest beautiful goodnight 😍😍😍
R: haha night Jackk 😊😍😍

*the next day, friday*

"Well did you get the deats about the date?" My best friend asked eagerly the second she saw me. "Jack just told me to be ready by 5, make a playlist and dress casual. Does casual count heels?" I asked, I take advantage of anytime I get to wear heels. "Awww that's cute, he's being all mysterious about it! And Regan, heels are not casual, but you could wear wedges..." She replied. "Oooooh good idea! I know exactly what im going to wear tomorrow! Thanks love!" I said exited. "Anytime babygirl!" She said.
I got home and I made a playlist, he never specified songs, but I really like Jack, so I'm going to put cute love songs and maybe some random in there.