Southern Indiana Waitress Gets Holiday Surprise with $500 Tip

A Southern Indiana waitress at LongHorn Steakhouse in Evansville got the surprise of a lifetime this past weekend when she received a $500 tip thanks to the generosity of Keith and Jane Gray Davis and their holiday tip challenge. Samantha, a server at LongHorn for two years, shared that she often works double shifts and spends her time babysitting her two young nephews, ages 3 and 4. Despite a challenging start to her day, Samantha’s positive and upbeat attitude left a lasting impression on the Davis family and their friends.

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Keith and his friends and family have made it a tradition to bless waitstaff around the holidays, and shared Samantha’s story on social media, highlighting her hard work and cheerful service. "Once we finished recording, she told us her day had started out rough, but she didn’t let that affect her service," Keith Davis wrote. The $500 tip, made possible by contributions from friends and family, turned Samantha’s day around and left her speechless.

Tip Challenge: A Heartwarming Holiday Tradition

For Keith and Jane Gray Davis, the holiday season is a time to give back. Over the years, the couple has organized tip challenges in Evansville and beyond, surprising waitstaff with large tips to brighten their holidays. From Christmas Day breakfasts at IHOP to ice cream shops in Navarre Beach, Florida, the Davises have traveled far and wide to spread joy. “It’s amazing what you learn about people and their stories after the cameras stop rolling,” Keith said. Their ultimate goal? To continue these acts of kindness throughout the year.

PHOTO: KEITH DAVIS TIP CHALLENGE

How You Can Join the Tip Challenge

These efforts are supported by donations from their friends, family, and the community. If you’d like to help them bless another hardworking server, contributions can be sent via Venmo (@Keith-Davis-46) or Apple Pay (618-383-3658). The couple plans to visit another local restaurant this weekend to share the holiday spirit.

This heartfelt tradition reminds us all of the power of kindness and generosity—especially during the holiday season.