Vanessa Goldschmidt said it had been a slow night at the pod of tables she was in charge of serving at Pequod's Pizza in Lincoln Park on Thursday.
The night quickly became a memorable one when, after cashing out one $45 tab, she was handed a $500 tip.
She was the latest unsuspecting restaurant server to experience Aaron Collins' last wish.
The Collins family began distributing $500 tips last year after the 30-year-old committed suicide in his hometown of Lexington, Ky.
The last line of the will that his brother Seth Collins, 33, found on Aaron's desktop computer made clear what he wanted: "Leave an awesome tip (and I don't mean 25 percent. I mean $500 on a (expletive) pizza) for a waiter or waitress."
In Chicago, the gesture unfolded at the pizzeria after Seth Collins had taken the last bite of his tomato and basil deep dish, and Goldschmidt, 34, was ready to cash him out.
"Actually hang on just a second," Collins said, launching into a story about his brother's untimely death and last request.
He handed her a stack of $20 bills along with a printed postcard he made featuring Aaron's name and photo.
"I'm like shaking right now. Are you kidding?" Goldschmidt said, lunging toward Collins for a hug. "Oh, my gosh. I'm shaking right now. That's amazing."
It was the 56th time since Aaron Collins' July 7, 2012, death that Seth Collins fulfilled the request from his brother's will.
Seth Collins had posted a video online of what happened when they made the first surprise tip in Kentucky last year. It inspired a wave of donations, and Collins made it his goal to take the experience out of Kentucky and give extravagant tips in all 50 states before Christmas, thus bringing him to Illinois this week.
He set up a nonprofit in Kentucky that he said holds about $60,000 from donors all over the world. To memorialize his brother, Collins said, he wants all the money to go toward gratuities for waiters and waitresses at local restaurants, many of whom are recommended by Facebook users who are following Collins' journey.
Sometimes Collins' parents and sisters attend the big-tip dinners with him, but he's going alone on this road trip, hoping his '99 Altima will keep up with him for 17,000 miles, he said. He has raised $5,600 so far to fund the trip through an Indiegogo campaign online.
Aaron Collins, who constructed homes in Kentucky and fixed computers, was a man who struggled in his life, said his mother, Tina Rae Collins. She wasn't in Chicago this week but said she has attended the tippings 15 to 20 times.
After his death, the family reacted to all the requests they found in his will. One example: They gave the $70 Aaron left behind to homeless people.
The $500 tip request made sense to the family. Taking friends out to dinner and leaving big tips behind was something Aaron Collins did often, his brother said. He got a kick from picking up a big tab at meals, and other random acts of kindness, Seth Collins said.
At family celebrations out, "he would reach down in his own pocket if he didn't think we had left enough," said Tina Rae Collins.
For her, distributing the tips is a way to find comfort in her loss.
"As sad as I am, I can't help but be happy and excited when I see what that little seed that Aaron planted has produced," she said in a phone interview.
"I read a lot of things about grief, about the loss of a child. Pretty much everybody says the only thing that they want is to hear their child's name spoken. They want to know their child meant something. … I don't have to worry about that."
On Thursday night, Goldschmidt, of Chicago, said the money would probably be used for her rent and other bills. She works full time at the pizzeria, relying heavily on tips, she said.
"It was just like another Thursday night, coming into work, hoping for the best. It's a slow night," Goldschmidt said after receiving the cash. "I'm just taken aback. It's such an amazing gesture."
Milwaukee, St. Paul and Des Moines are the next cities on Collins' list to visit.
"It'll never get old," Seth Collins said.Copyright © 2015, RedEye