Admittedly not a big fan of photo shoots, Dan Gilbert asked the group on the other side of the camera to rattle off a few jokes; anything to force a smile while he posed for photographer Don Bensman. Regrettably, if there’s anything I’m really, really, bad at, it’s remembering jokes. I couldn’t even think of a good University of Michigan one-liner for Gilbert, who, as a Michigan State grad, no doubt would have appreciated as much.

Fortunately, a Cavaliers representative came up with something about a bear walking into a bar, and Gilbert — as you can see from the cover of this month’s issue of CBC — gave us his best grin for a half-hour on a recent Sunday afternoon.

More often than not, Gilbert was the one who had everyone laughing inside the Quicken Loans Arena conference room, just an hour before his Cavaliers were slated to take the court against the Boston Celtics. Although a billionaire, he seems like an ordinary (albeit busy) 48-year-old guy from Detroit. I was appreciative of that, considering I’m a month shy of being an ordinary 46-year-old guy from Cleveland. We have at least a little bit in common, not counting a few million bucks here and there.

While discussing “Red Right 88” — the Brian Sipe interception that Gilbert happened to witness in person inside Cleveland Stadium in 1981 — I noted that I had cried after the Browns’ playoff loss that winter day. Sheepishly, I added that I was  a junior in high school at the time and was probably a little too old to be shedding tears over a sporting event.

“What are you talking about?” Gilbert shot back. “I still haven’t STOPPED crying since Game 6 last year.”

“Game 6” would be the Cavaliers’ season-ending playoff loss to the Orlando Magic. Blessed with home-court advantage throughout the playoffs, Cleveland nonetheless fell six victories shy of the franchise’s first title ever and the city’s first championship since 1964.

Although Gilbert brought up the loss in jest, I sense that he really was bothered by the defeat, at least for a short time. Likewise, I get the feeling he really does care about the city of Cleveland, which is the theme of our cover story on Gilbert on page 29.

Certainly, Cleveland — dubbed the “most miserable” city in the country by Forbes magazine — could use Gilbert’s help these days. Like the Cavs owner, we’re all looking for reasons to make us smile. An NBA championship would fit the bill perfectly, but any joke will do. As long as it’s not on us for a change.