It shows that more attractive waitresses get the biggest tips, an academic study has found. Charlie “The Singing Waitress” Jennings, shares a laugh with customer Allen. Charlie “The Singing Waitress” Jennings, shares a laugh with customer Allen. Melissa Lombardo, 22, says she will use the $1,000 tip to further her. The best way to get a tip for the, Blonde waitress know show to get her tip.