"Are you guys saying I'm boring?" Halladay said with a smile when two reporters approached and asked where the sense of humor emerged from.
Three years later, Halladay is retired. He is relaxed. He is no longer overwhelmed by the burden of being Roy Halladay, the pitching perfectionist paid to help his team win not only on the days he pitches, but every other day, too.
And he is showing off that sense of humor regularly. Halladay joined Twitter (@RoyHalladay) this spring, in an effort to spread word about a charity event, and has ended up showing off his personality in the process.
"I found it was a way to let people see who you are," Halladay said. "We talked about it today. When I'm at the field, it was business; you were working and that's who you are. People never see the other side except my wife and kids - and they are probably annoyed by it. I'm sure people will be at some point. It just became fun to be yourself, let your guard down, and I've always had fun making fun of myself and not taking things too serious."
Roy Halladay, tweeting a selfie while flying a plane. Roy Halladay, using Twitter to write a quasi-love letter to his favorite player in baseball, Chase Utley.
Roy Halladay, not taking things too serious.
Before arriving at Citizens Bank Park yesterday, where he would throw the ceremonial first pitch to open Alumni Weekend, Halladay went to the Philadelphia Zoo.
Why? Because 4 years ago some guy decided to create a silly blog called "I Want to Go To The Zoo With Roy Halladay," a Phillies-centric website that's light on the baseball and heavy on the humor. And, of course, Halladay and Zoo With Roy became fast friends shortly after Halladay arrived on Twitter.
And so they went to the zoo.
"He's Roy Halladay and he shows up in a gold Chevy Malibu," said anonymous South Philadelphia native Zoo With Roy, who lives in suburban Washington, D.C., and works in the government. "He's not big time. He's very humble . . . He was super, super nice."
Roy Halladay, dream maker.
But the recently retired pitcher, who threw a strike to former battery mate Carlos Ruiz after coiling into his familiar windup from the mound for his ceremonial first pitch, doesn't plan on spending the rest of his life flying planes or messing around on Twitter. He isn't finished with baseball, actually.
Halladay realized how much he needed to still be involved in the game when he arrived in Clearwater this spring to work as a guest instructor for a few weeks.
"I kind of had these thoughts of maybe being a [general manager]," Halladay said. "But once I got there I realized how much I actually loved just talking to guys and talking about the mental side, talking about mechanics. Teaching, really. Teaching and just sharing what I've learned that's been given to me for free. So, I've been doing that here and there. I plan on going to school working on a psychology degree and go from there."
Halladay, not surprisingly, sounds like he has a game plan.
After reaching the big leagues a decade and a half ago - and coming one out away from a no-hitter in his second career start - Halladay struggled mightily and found himself banished from the big leagues to Class A. There he discovered the importance of the mental side of the game, using Harvey Dorfman's "The Mental ABC's of Pitching" as his own personal bible.
Halladay struck up a friendship with Dorfman and, when Dorfman passed away a few years ago, credited him for steering his career in the direction for success. Halladay would like to pay that forward.
"I don't know if it's my calling, but I think that it's unique," Halladay said. "I had a chance to go through almost everything. You know, I've, from growing up, at times being pushed. Struggling, not just a little bit, but a lot. And then starting to understand what's going on, starting to understand what Harvey's talking about, and really just trying to morph myself into what I was hearing, and what I was - and I became that, I feel like I became that.
"So it's unique to be able to go through all of those experiences you can have and come out on the other end with that knowledge. You know, I could pretty well regurgitate anything Harvey ever said. But there are special circumstances, which is why I'd like to go to college. I just think that's something that I can offer back to baseball. And working with players, at all levels. Going home and just seeing what a mess youth baseball was was an eye-opener. I just want to make it a better game. And it's been a lot of fun doing that already."
Halladay has already started working with an important member of the Phillies organization, former first-round pick Jesse Biddle, who took a mental break for 6 weeks this summer after struggling in the season's first 3 months and battling a crisis of confidence.
Biddle, 22, returned to the mound Wednesday and threw five no-hit innings at Class A Clearwater.
"He's a good kid," Halladay said. "It's just exactly like me - exactly like me - you really talk about simplifying things, that's where they don't really get what that means. They think if they simplify and if I take away my slider and changeup - no. We're talking about thinking about one pitch, and having that calm, intense focus to do one thing and think about one thing only. And that's what we've been talking a lot about.
"I think he's starting to get there. But it's not something where you can read the book and do it, someone can't tell you and do it, you really have to live it. It has to be something you have to try and live. He's doing better. I think he's feeling better. But I think the hardest thing for people to realize is what they can and can't control. I think they get caught up in that a lot. So, having him understand what's in his control, I think has helped him."
Retirement has been good to Halladay.
He's coaching his sons' baseball teams, he worked toward getting his piloting license, and, through social media, he has managed to connect further with a rabid fan base that already idolized him.
But when his two boys are through high school and onto college - or, perhaps, onto their own baseball-playing careers - Halladay could very well be back in a big-league ballpark, arriving early, with a plan and a purpose.
On Twitter: @ryanlawrence21