(COLORADO SPRINGS) — In May, several students at Air Academy would hear the news they had been awarded with a scholarship or grant from the Riley I Whitelaw Memorial Fund.

One of those students was Lilly Rottenborn.

“So I was pretty surprised when I got a grant just because I don’t consider myself to be a super artistic person,” Rottenborn said. “When I think of art, I think of the first thing that probably comes to a lot of people’s minds is like drawing and painting or maybe sculpting and I am not very talented at any of those things.”

Rottenborn received one of the art grants, which will go toward her love for singing.

“So when I was trying to think about what I could use this grant for, I was considering my passions and something that I really love to do is sing,” Rottenborn said. “And so I’ll sing at work, I’ll sing at home, I’ll sing in the shower. So I decided that I would like to take some voice lessons. I’ve never had any formal training with singing, so now I’ve taken three voice lessons and I have one more.”

There is a deeper connection for Rottenborn who recalled her friendship with Riley back when they met in sixth grade.

“So I met her when I was in sixth grade,” Rottenborn said. “We went to the same school, and then in our freshman year, we were both in our speech and debate team… so we worked together to memorize and kind of formulate a script. And we were two old men kind of bickering back and forth at each other.”

Whitelaw and Rottenborn practice debate together. Courtesy: Rottenborn.

The kindness and positivity of Riley Whitelaw is one that Rottenborn emphasized. Rottenborn also shared how she believes Riley is cheering her on while she sings.

“I think the really special thing about it is that Riley encourages people to pursue passions,” Rottenborn said. “She’s a cheerleader and so I think it does feel like she’s just cheering me on and being like, yes, this is something that excites you and brings joy into your life. And so I think she would be really delighted to see what she’s been able to do.”

Riley’s mother, Courtenay Whitelaw, shared the reason behind creating the Riley I Whitelaw Memorial Fund.

“In the early days of losing her, I remember looking at a picture of her and just getting this sense of her telling me like, ‘Mom, you really need to take care of my friends in my classmates’,” Courtenay Whitelaw said. “And so that was sort of my first inclination of, I had to do something to kind of carry her forward and make sure that I’m taking care of not only her friends, but kids in general, because that’s what she would want us to do.”

Students filled out an application and then a team of teachers and staff at Air Academy helped select the recipients.

“So the scholarships and the grants were kind of a team of teachers and administrators at Air Academy High School that helped me pick the scholarships,” Whitelaw said. “The kids applied, and then we had to go through all the applications and decide who was more deserving, which was not easy.”

In her interview with FOX21, Whitelaw wore a purple shirt with the phrase “kindness matters” on it – the motto that Riley believed in.

“So I have always seen Riley as very giving of herself, always there for others,” Whitelaw said. “She was like a true empath. We talked about it a lot, about empathy, and she just embodied that empathy and being very giving towards others.”

Evidently, Riley’s positivity was seen by those who crossed paths with her. She received the nickname Smiley Riley from a school principal.

“Smiley Riley, that was a common theme throughout her life that people noticed,” Whitelaw said. “She always had a smile on her face, and she was coined Smiley Riley, even by her principal. But even before her high school years, she was known as Smiley Riley.”

Courtenay Whitelaw and Riley Whitelaw on top of the Manitou Springs Incline. Courtesy: Mike Duran.

While Riley is no longer here on earth, her mom is reminded of her presence every single day.

“So knowing and feeling her presence definitely carries me,” Whitelaw said. “And I know again, like in the very early days, I just remember Riley sitting on the edge of my bed like we always would have our nightly check ins.”

Riley getting a tattoo that would match her mother’s. Courtesy: Mike Duran

The two are forever connected through a matching tattoo, which Riley begged her mother to get.

“On the really bad days where I’m struggling, I just can look down at my tattoos [on] this one, which was the one that we got together,” said Whitelaw.

Courtenay Whitelaw looks down on the matching tattoo and smiles. Courtesy: Mike Duran.

July 22 will be Riley’s Graduation Benefit, an event open to anyone to raise money for the fund, with the proceeds going towards scholarships and grants that exemplify the same traits as Riley.

In carrying her positive outlook on life, Rottenborn shared a message she hopes people will emulate about her friend.

“If you know them well or if you don’t know them well, if they’re grieving, if they’re struggling in a small way or in a big way, I think you can be like Riley and try to understand what’s happening and figure out how to bring some joy and some relief to that grief and heaviness, you know?” said Rottenborn.