The conversations have ranged from excited to wistful to comical, albeit there are absolutely no regrets. There is, however, some contemplation of the what-ifs.
These conversations take place between Shawn Montague, Luis Cartagena, and Nick DeGennaro, once inexperienced teammates on a youth-laden Yorktown High roster over-packed with guards.
"We talk all the time about what would happen if all three of us (were at Yorktown) this year," said Montague, a 6-foot-6 senior at Canterbury Prep and currently one of the northeast area's most highly-acclaimed, high-upside, unsigned Class of 2016 recruits.
"We could have done some great things together, I'll tell you that. My sophomore year at Yorktown, we struggled but we had great players like Mason Dyslin, Ricky Corrado, and Anthony Coutsouros. Those guys were a big part of our team and led by example."
Ahh, respect. Respect for one's elders shows character.
The high-character, high academics and high-rising of Montague has attracted Division-I programs all across the eastern seaboard.
Manhattan, Bryant, Fairfield, Central Connecticut, Rider, Chattanooga, Canisius, New Orleans, and Seton Hall have all offered.
Boston U, Minnesota, and even Florida inquired at one point.
Bryant, Manhattan, St. Bonaventure and suddenly Siena are all in aggressive pursuit of the 6-foot-6, 180-pound guard.
The past two seasons, the senior has evolved into a high-efficiency threat around the rim, displaying explosiveness on baseline drives and a deft transition game.
These factors initially molded Montague into an appealing fit for the souped-up brand of basketball enforced by Canterbury head coach Keith Rado.
Rado's consistent work with Montague has churned out a fundamentally sound prospect with an increased vertical. Montague arrived at the doorstep skinny, extremely raw, and still learning how to contribute at such a high caliber level.
A stockpile of injuries opened up the opportunity for immediate meaningful playing time for Montague, who reclassified after playing sparingly at Yorktown as a sophomore.
Applying plenty of old school tactics, Rado will even have his players carrying bricks through arduous stretches of practice.
He emphasizes running and increased cardio work.
It's a necessity given the frenetic-paced identity of his program, which has long thrived on length and athleticism and an unwavering lungs burning attack.
Canterbury scored 110 points in a game this season, with Montague a linchpin in the system.
"Shawnie's athleticism is off the hook and he hasn't even come close to reaching his potential yet," said Rado, who starred at nearby Naugatuck (CT) and won a Division-II national championship under Dave Bike at (now Division-I) Sacred Heart.
"The thing with Shawn when he got here, the biggest thing was his aggressiveness. He was more of an East/West type of player. Now he's a North/South type of player. He's a kid that attacks the basket hard. He's a catch-and-shoot 3-point shooter, he can shoot it with consistency. He's top-shelf all around. He's an even better kid than he is a player, which I think is most impressive about him."
Montague's jumper, increased defensive IQ, above-the-rim finishes, and a package of off-the-dribble moves enabled him to transfer from strictly a pull-up threat to an instinctive playmaker.
A longtime devotee to the philosophy that making practice Hell renders the game Heaven, Redo describes a wowing improvement.
"He's brought up his intensity in practice," Redo said.
"I coached (Louisville guard) Donovan Mitchell as a sophomore, the area where he and Shawnie are both similar is athleticism. The big thing about Shawn is he will get to (Mitchell's) level. He didn't come in as a superstar, coming from one program to the other. He went from barely playing any varsity basketball to being one of the best players in the league."
While his game blossomed way up the Merritt Parkway, Montague still kept tabs on his former teammates in Westchester County.
Cartagena, who erupted at the tail end of his sophomore year, transferred to White Plains.
The hard attacking lefty averaged 20 points, three assists, three rebounds, and two steals as a senior this season.
DeGennaro helped revive Yorktown under Kevin Downes, emerging into one of the Section's top scoring and creating threats with 18 points and five assists per game.
Montague can only smile at the notion of this triumvirate playing out their senior year together. He is still tight with both DeGennaro and Cartagena.
The trio, despite never being reunited on the court, vows to continue to provide moral support for each other as they open the next chapter in their careers.
And where will be next for Montague?
"Last Monday, St. Bonaventure came down to work him out. He went up to Siena on Wednesday," Redo said.
"San Diego is coming up on Monday. Utah, they're definitely showing a lot of interest right now. They're in the process of recruiting him. They love the film they just want to meet him in person."
Montague missed seven games this season, due to a concussion he sustained in the season-opener against Cheshire Academy.
He returned to get hot at the opportune time.
He dropped 27 points against Trinity Pawling, 24 vs Wilbraham & Monson, 25 v.s Taft, 25 v.s. Berkshire, and 20 v.s Hotchkiss. As a 17 PPG scorer, Montague was named first team Tri-State and third team All-New England.
"I plan to make my decision soon, I just want to go to a school where I can excel on and off the court," Montague said.
Redo noticed a change in Montague when he brought his team to the University of Connecticut for a summer workout.
Energized for a unique challenge, Montague held tough against Huskies guards such as Sterling Gibbs and Rodney Purvis.
Montague's father, Anthony Montague, is Manhattanville's all-time leading scorer with 1,885 points from 1985-1989.
"My Dad emphasizes playing hard at all times, because you never know who is watching you," Montague said.
"He and my mother Linnie have pushed me like nobody else has, when nobody else would. I wouldn't be in the position I am in today without those two in my life."