Jimmy was stunned when the homeless man he’d bought coffee for earlier boarded the plane and sat beside him in first class. Who was he, and why had he asked for money in the first place?
Three months ago, Kathy walked into his life, and within weeks, she became his world. People called him crazy for proposing after just a month, but it felt like destiny. Now, he was flying out to meet her parents for the first time, and her father, David, had a reputation for being stern and hard to impress.
Nerves pushed Jimmy to arrive at the airport early, where he ducked into a coffee shop to kill time. That’s when he noticed him—a man in tattered clothes, his face worn with age. He asked Jimmy for some change for a coffee, specifically Jamaican Blue Mountain, because it was his birthday.
Skeptical at first, Jimmy decided to buy the coffee and a slice of cake for the man. The stranger’s name was David, and he shared his story of losing everything—his family, his job, his home—and how life had broken him. Jimmy, moved by his raw honesty, slipped him $100 before leaving.
Hours later, Jimmy boarded his flight, still thinking about the man. As he settled in first class, his heart skipped a beat when the same man, now in a sharp suit, sat next to him.
“Mind if I join you?” David asked with a smirk.
“Wait… you’re her dad?” Jimmy stammered.
“The very same,” David replied. “I wanted to see who my daughter’s fiancé really is, outside the polished dinner introductions. You passed the first part.”
Jimmy was in shock. David had been testing him. “A test?”
David nodded, pulling out a notebook. “Now, write a letter to Kathy. Tell her why you love her, why you want to marry her, and how you’ll take care of her.”
Reluctantly, Jimmy wrote, pouring his heart out about how Kathy made him feel complete, how he wanted to build a life with her. When he handed the letter to David, he was told, “You passed. Welcome to the family.”
After landing, Jimmy was still processing the experience. At Kathy’s parents’ house, David watched him closely during dinner, offering little in terms of approval. It wasn’t until the end of the meal that David gave his blessing: “You’ve shown me who you really are.”
Later, while helping Kathy’s family clean up, Jimmy found a receipt for the coffee he bought David. At the bottom was an extra charge: “$100 donation.” Confused, he asked Kathy about it.
“Oh, that’s my dad’s way of tying up loose ends,” she said with a sly smile. “You didn’t think it was just about the coffee, did you? And how do you think Dad knew about your flight?”
Jimmy realized he wasn’t marrying into a regular family. Kathy’s family was unique, and their tests weren’t just about passing—but about understanding generosity and what it meant to be part of their world.
