Jack had his heart broken once in high school and swore never to love again.
- All his dedication was to his business.
He only felt close to his mom and sister but otherwise avoided interacting with women at all costs. His friends always thought he was gay, but Jack was just terrified of being hurt again. One day, a friend invited him to the house for a small dinner event. He’d invited some friends from college and wanted Jack there. Jack tried to get out of it, but his friend wouldn’t accept any excuses. Jack showed up to the dinner with an expensive bottle of wine and no intention of interacting a lot. But he was mesmerized by this girl he’d never seen before. It turns out his friend’s sister was also at the event and caught Jack’s eye. Despite his better judgment, they spoke that night, planned a date, and began dating a few months later. Their relationship progressed when Jack took his girlfriend to Libertyville to see his mom last month. It was fall, and the temperature was already dropping. His mom’s house felt so lovely with the furnace running as she welcomed them home. His mom was not merciful as she told tales of how she thought her son would never bring a girl home. Jack felt like running away the whole time, but his girlfriend and mom truly bonded during that trip. Jack had planned a surprise for his girl and proposed to her as she laughed so hard at one of his mom’s jokes. She stopped mid-way and instantly started crying because of the surprise. His mom, too, was crying, and now Jack had two women he had to comfort crying out of joy.