His father added to that hope with the motivation.
"My dad sat me down," Dearring recalled, "and he was like, "if you really work hard at this and you really want this, you can take this as far as you want."
Darren Dearring spoke from experience. Basketball was a huge part of Darren's life. He played basketball at Virginia and eventually coached some top AAU basketball teams in the state of Minnesota. When Riley was growing up, Darren would put a little basketball in his hands and would take his son along to his summer league games.
"Basketball became really important from day one," Dearring said. "I had always grown up watching him play, so the game was always around it. It just became a habit."
It's a habit he hopes will pay off with a successful career at the University of Wisconsin and carry on a long legacy of Minnesota natives coming across the border to play for Bo Ryan and his staff; players like Jon Leuer, Jordan Taylor, Jared Berggren, Mike Bruesewitz and others.
And like a lot of those players, Wisconsin identified Dearring as a player who could help them from a young age, as the Badgers were the first school to send Dearring mail, even before home state Minnesota showed interest.
"It was a weird moment because you always watch these teams on TV," said Dearring. "The letters make you go, ‘Dang, maybe one day I could be playing for them."
Wisconsin associate head coach Greg Gard has been responsible recruiting the state of Minnesota for the Badgers since his arrival with Ryan in 2001; a tenure that has allowed him to establish many valuable connections.
One of those connections is Tom Dasovich, who Gard knew from his time recruiting Bruesewitz at Henry Sibley. Dasovich had moved on to Minnetonka where he began to coach Dearring, who had played at Hopkins and De LaSalle before Minnetonka.
"They are willing to share information with us in terms of who is playing well and who has a chance to be a very good player down the road," said Gard. "It was just a matter of word of mouth and knowing the right people.
"Riley was well known and had very high accolades as a junior high player coming into high school. He had a chance to be a very good player in high school. It was just a matter of getting his feet underneath him and developing."
That developed started during the summer following his sophomore season when he first noticed coaches coming to see him. It was then that he started to focus on the school, coaching staff and the best system he would fit into.
A lot of his family is from Racine, Wis., so Dearring already had a good foundation of what it was like to be a fan of the Badgers and the program; a program known for recruiting hard-working players who liked to play aggressive on both ends of the floor by sticking their nose into opponents.
Having known Gard since seventh grade from the associate head coach's presence at his high school practices, games and tournaments, Dearring already felt comfortable with Wisconsin. After meeting Ryan and getting an offer, Dearring only needed a few days before saying yes.
"He showed so much tradition and I had so much respect for him that it made my decision really easy," said Dearring of Ryan. "I really fell in love with the tradition that they had here, and coach Ryan and what he tries to teach his players, how he develops his players. Wisconsin does pretty well with Minnesota guys, too, as we've seen."
Wisconsin's Minnesota players admit to circling tonight's game on the calendar, a chance to go home and play in front of family and friends. Dearring is no different, but the only scholarship Minnesota native on UW's roster will be a spectator tonight when No.9 Wisconsin (16-2, 3-2 Big Ten) take on Minnesota (14-5, 3-3) at Williams Arena.
One of six true freshmen signed by Wisconsin and entering a roster full of experienced guards, Dearring made the decision early in the fall to redshirt and improve his craft.
"We are really guard heavy this year," said Dearring. "I thought it would make more sense to take my time to get stronger, develop more and when there's less guys and I'm more ready, I can contribute to the team the best that I could. Right now I am contributing in practice, trying to compete with guys and give them what I've got every day."
Watching Dearring go through a recent practice, Gard pointed out Dearring's weight gain, which allowed him to fight for rebounds in the paint, aggressively defend UW's veteran guards and show some confidence in his jump shot; things he wasn't able to do consistently when he first stepped foot on campus. All things that signaled that Dearring is trending in the right direction.
"I think he is nowhere near where he's going to be as a player, (but) this year has been very good for him already," said Gard. "He's added some strength, added some weight and added some confidence, which is the big thing. I think as you get stronger, get older, feel better, bigger and stronger, your confidence grows. We're looking forward to him and his future. We think it's going to be very, very bright."