I Went Homeless Trying To Impress My Crush



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“Oh thank you, Dexter,” Kaylie screamed as I handed her the keys to her brand new mercedes.

Now, I know what you must be thinking, getting your crush a car is a bit overboard, but if it meant getting her to like me then I was more than willing to do it.

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I met Kaylie when her father, Mr. Clarke, at one of our conference meetings, said that he wanted Kaylie to get to know the ropes of the company.

Kaylie had a reputation for always being in the spotlight with new boyfriends and every weekend she was in a different country. Mr. Clarke knew that if she continued her shenanigans it would reflect badly on his company.

“Mr. Hall,” Mr. Clarke said looking directly at me, “Kaylie will be working as the head of the accounts department, so you will now answer directly to her.”

Kaylie wasn’t a basic woman. She had the body of a model. She was always, in the latest fashion, she drove the latest car, and her hair and nails were always done. I knew that I wanted to be with her ever since I laid eyes on her but I knew that she would never date a man like me.

I drove the same car that I did in college, my salary wasn’t anything to be excited about and my wardrobe was filled with worn out suits and shoes, and well, my glasses, were a whole other story. I knew if I ever wanted a shot with Kaylie that I needed to step my game up.

After work I went to the mall and got myself contacts and a whole new wardrobe. I even traded in my old car and got myself a new one. My parents always encouraged me to save and since I was not in the dating pool I was able to save quite a lot over the years.

The next day my coworkers definitely noticed and I got a few notes on my desk from female coworkers which included their numbers but my eyes were only for Kaylie. I already imagined Kaylie being swept off her feet by my charming demeanour and relaxing in each other’s arms watching Netflix on the weekends.

With Kaylie’s birthday right around the corner I knew that purchasing the right gift would give me that foot in the door that I desperately needed. The next few days Kaylie spoke to me at least twice and it was a start since she had never looked in my direction before. I guess the makeover was working.

The week leading up to Kaylie’s birthday I sent her flowers and wine with a note every day telling her to enjoy her day. On the eighth day I mustered up all the courage I had and knocked on the door to her office.

“Hi, Ms. Clarke, can I have a word with you?” I asked nervously.

“Hi, Dexter. Come in and please call me Kaylie,” she smiled.

“Did you like the wine and flowers that I sent?”

“I did, thank you. It didn’t have a name so I didn’t know who to thank. That was very thoughtful of you,”

I cleared my throat, “Would you like to go on a date with me tonight?”

“Oh. Um, actually my father and I have a dinner date tonight, but maybe another time?”

I nodded and left the office heart broken. The rest of the day I pondered on a gift that would make her say yes for the next time I planned to ask her on a date. By the end of the day I knew what I was going to get Kaylie and this time she couldn’t say no.

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