"I thought, 'This has got to be a joke. There's no way,'" Kasey Simmons of Little Elm told ABC News on Tuesday. "Then, I read that letter and I'm thinking, 'This $500 tip is for real, dude!'"
Simmons, 32, was working the dinner shift at an Applebee's restaurant in his hometown last Tuesday when a patron left the 135,000-percent tip on his table.
Earlier that day, Simmons had paid for a stranger's grocery bill at a Kroger supermarket nearby.
"I noticed there was a lady standing in front of me," he said. "It looked like she had been crying, because once in a while she'd glance over to me. I go up to her and say, 'It's not raining inside. There's no reason to look so down. I'm sure you have a beautiful smile because you are a beautiful lady.'"
"It looked like she had a bad day. She kind of shut me down a little bit. I wanted to make her at least grin a little bit, and it wasn't happening."
Simmons offered to pay for the woman's $17 grocery bill. After some coaxing, the stranger agreed, and Simmons succeeded in making her smile. He handed her his Applebee's business card before bidding her farewell and heading to work, he said.
"Every time I get to work, I say, 'It's a great day. I'm going to make some friends and make some money,'" Simmons said. "This day happened to be the worst day of my Applebee's career. I was having such a bad night that I was about to walk out of [that] place, and this lady comes in and I said, 'Hey, my name's Kasey. I'm just letting you know that I am so far behind and I'm in the weeds right now.'"
Simmons told the customer that it would be about 45 minutes before he could wait on her and her family. He offered to buy the drinks, which was all they ordered.
Simmons later returned with a 65-cent check for a flavored water, the cheapest item on the menu, a request from the diner so she could leave a tip, Simmons said.
"By this point I said, 'This lady's crazy,'" Simmons joked. "I brought her the check, and she asked me to split the 65 cents between two credit cards and I said, 'Are you serious?' I think she wanted to see if I was a real nice guy or a fake nice guy. The real nice guy splits it, and brings the lady her check."
Simmons divided the check, placing 37 cents on one receipt. The woman left Simmons $500 on that one, making a grand total of $500.37.
Sitting on the table was also a note that read, in part:
"On behalf of the Sullivan family, I want to thank you for being the person you are. On one of the most depressing days of the year, (the death of my father's 3 year anniversary) you made my mother's day wonderful. She has been smiling since you did what you did."
Simmons was shocked by the huge tip.
"Even with what I did at the grocery store, I would want someone to do for my daughter, mom or grandmother," he said. "If they looked the way that woman did at Kroger, I would pray you would do the same."
Simmons said he hopes to meet the family face-to-face to express his gratitude.