A Christmas Makeover

Christmas in Chicago is magical. The lights, store windows and Millenium Park's Ice Skating. Everything about it puts you in the Holiday mood. It's hard not to feel happy this time of year. Except if you are Jaime. Jaime is a beautiful young lady who lost her husband shortly after they married. Ever since then, she sticks to her routine, works at the library, and enjoys time with her cat.
She thought she was happy enough, adjusting to her new life, but one day everythign started to change unexpectedly. Justin was the head construction worker in charge of their library remodel. Jaime and Justin developed a friendship over the past year. One day, it seemed like several people who worked with her at once were telling her she needed to go out and have some fun again. How could she? Rick was gone, and she was content in her life now.
After getting frustrated after someone told her she should go out, she blurted out to Justin "how do you do it? how do you go out to bars, mingle, date, and stuff like that?" He laughed, and said "actually I am more of a homebody these days, but why do you ask?" She felt embarrased, she explained to him her story. He had no idea. After she finished, he said he had an idea. Let him be her wingman, he would go with her to places, make sure she was safe, give her pointers etc. She thought it was ridiculous, but reluctantly agreed to 4 times, once a week for a month mostly just to shut everyone up.
Little did she know what she was looking for was right in front of her eyes.