Ron Howard is a ridiculously nice guy.

It’s late into a long day of shooting on The Dilemma and I’m sitting with a small group of journalists in the back corner of an artificially constructed auto shop. Called “B&V” after Kevin James’ and Vince Vaughn’s characters, Nick Backman and Ronny Valentine, the place has been constructed in an empty Chicago studio and seems to fill the entire building. There are no breakaway walls or false backdrops, so even though the scene’s getting set up across the shop, the set continues all around the camera, including an authentic office, complete with a drawing table, car sketches, body designs and even a rack of board games for when the characters need to take a break.

It’s been most of a day and we’re waiting on one final interview when Ron Howard makes a pass to check up on us. He already did a lengthy interview first thing in the morning, but he makes frequent stops to our group to make sure we’re still having a good time.

It may come as no big surprise that Howard is, through and through, outgoing and friendly. He has the same grin that he had as a kid on “The Andy Griffith Show” and still maintains the wholesome charisma of “Happy Days'” Richie Cunningham. But Howard is a personality that, through the years, has also grown to be associated with some critically lauded films like Apollo 13, A Beautiful Mind and Frost/Nixon. While nowadays he’s a name you expect to be hearing around Academy Awards time, The Dilemma represents a return to the comedic style of filmmaking that the director launched his career with, one that he compares to one of his very first directing gigs, Night Shift.

“When I went home over the Fourth of July weekend, I actually threw ‘Night Shift’ into the DVD player,” Howard recalls, “…I really feel that, even though the stories aren’t similar, there’s the brushing up against certain circumstances that are a little bit edgier and then watching people navigate that. This is really, in a what I hope is a funny and entertaining way, a kind of a gauntlet for the Ronny Valentine character.”

In the film, Ronny and Nick are best friends and business partners, on the verge of a deal that could make or break their auto shop. Just as the pressure is building in their business affairs, Ronny happens to oversee Nick’s wife (Winona Ryder) cheating on Nick with another man (Channing Tatum). Unsure of whether or not to tell Nick and troubled by the notion that the reveal could harm both their friendship and their business, Ronny is forced to deal with his conscience while trying to learn more about what’s really going on and what he ultimately has to do.

“[Ronny has] got his foibles,” Howard explains, “He’s got his flaws. He’s been battling them. Things are looking pretty good, but damned if the rug doesn’t just get yanked out from underneath him and he doesn’t know what the hell is quite happening to him That’s what smart about it. We don’t all know. We can’t know what’s really going on with people. It puts all the characters in a fun pressure-cooker.”

It wasn’t so much the character of Valentine, though, as the situation itself that drew Vaughn to the script. Approached by producer Brian Grazer, Vaughn found a comedic quality to the story that he could bring his own style to, right down to moving the setting of the film to his hometown Chicago.

“I mean the fun thing, the interesting concept with the movie is that it’s not someone you just know,” Vaughn says, “It’s not someone who’s sort of a friend but it’s really your closest friend. You find out that the wife is doing things, but you’ve also known her for awhile. So what is the appropriate way to break the news or tell the news? Do you go to her first? Do you give her a chance? Do you go to him? So the concept of the movie is, ‘Do you tell or don’t you tell?’ The concept of the movie is how you navigate it and maintain the friendship. What’s the right thing to do preserve the relationship?”

When it comes to Vaughn and his co-star, the actors can only sing one another’s praises. In James, Vaughn claims to have found someone to act against that is both funny but also genuine and whose emotions the audience will not only buy Ronny caring about, but will hopefully find themselves invested in as well.

“I have to say that this man is a savant at making the script better,” says James of working with Vaughn, “From what we had (which I loved when I first read it), you add to that how excited I was to work with Vince… and then Ron Howard. It was a no brainer for me. Honestly, it would’ve been tougher and I probably still would’ve done it if I didn’t love the script because I love these guys so much. But I did love the script. That was the base of it. When we got in there and we started working on it I have to say that it was really Vince who spearheaded and just changed it and every day. I remember I’d go to sleep at night and go, ‘Man, he made this better again.'”

Having two comedic leads at his disposal lead Howard to introduce a new step to his filmmaking process, encouraging the actors to improvise lines as part of special “free takes,” designed to liven up the atmosphere whenever Howard felt that too much repetition was making the scene go stale.

“Vince, of course, always does that,” says Howard of improvisation, “He encourages it and is excited by it. Kevin is undaunted by that kind of thing… Basically, we’ve got a great script that we like and in any given angle, if we think there’s a chance or if Kevin or Vince or I want to try something, we just sort of do a free one. Sometimes we’ll do the free ones and then we’ll go back to a tight one. A scripted one. Sometimes what they’ve done in the improv skewing slightly what they do with the scripted version. We know what’s good and tight, but if there’s another neat little spin on it, it’s a creative way to go fast and not really bog down the schedule. Even when they go off in the corner to some subject that you wouldn’t ever deal with, almost invariably there’s something in those free takes that I feel like we’re going to be glad to have in the editing room. Just again to breath as much of a modern kind of contemporary slice of life into it. This is not a set-up punchline kind of comedy. I really wanted all that honesty.”

Though improvisation may be old hand for Vaughn and James, not all the characters came from such a comedy background, though Howard was impressed by how well his leading ladies are able to hold their own when it comes to free takes. Jennifer Connelly, who plays Ronny’s girlfriend, Beth, previously worked with Howard on A Beautiful Mind. Falling into character for her was easy, except for one small talent that she ended up having to master.

“I was so nervous,” Connelly laughs, “I had to play ping-pong in this movie. The first day that I showed up and I said, ‘Ron. I’m really going to give this my all, but you might want to have a ping-pong double.’ Right now, my moniker at home is ‘Snake Hands’ Connelly. I’m just not down with the paddle and the whole hand-eye coordination thing. It’s not a thing that I grew up doing a lot of. No skills in the back pocket with the ping-pong. I worked on that. I worked on that really hard, I have to say I had a ping-pong coach. We got a ping-pong table in the hotel and anyone I could wrangle to come play ping-pong with me I’d get up there playing ping-pong.”

While the day’s scenes are confined to the auto shop, shooting on The Dilemma has fully embraced its Chicago setting, adding elements like the Blackhawks, the popular local restaurant Weiner Circle and incorporated outdoor shooting such as an arboretum scene where Ron’s brother, Clint, gets to make a guest appearance as a botanist. Though Howard shot in Chicago two decades ago for Backdraft, he explains that The Dilemma gives him a chance to really embrace the city’s own modern culture in a way that he refers to as “Midwestern Badass.” Though the town may be Vaughn’s home, James has found a way to make Chicago play to his strengths as well.

“[F]or some reason, and I don’t know why,” James says, “I don’t think that I’m funny in California. So I always want to do my movies east somewhere. I’ve been in Chicago a few times to do press but for a couple of days each time and I’ve never gotten to experience the city. I’ve experienced it with [Vince] and his family and his friends and you just see that it’s really like what John Hughes does. It’s a slice of life. It’s just such great people and it gives you such a great feeling and you want to shoot here and you want to be funny and you really feel like you connect with everybody here.”

Though the entire cast and crew wound up being very secretive about where the film ultimately goes (it looks like we can expect quite a few twists and turns), the day’s primary scene involved Ronny sitting on a couch in the auto shop with Nick. Ronny appeared to be having an allergic reaction to something (or, perhaps is just suffering from psychosomatic stress) and is covered in red hives. He tries to pull Nick away from work for a minute, attempting to broach the subject of their respective significant others and also discuss his own plans to propose to Beth, but finds that Nick is just too wound up in the upcoming business deal to pay any attention.

The scene wraps and Ryder and Connelly enter for the next. Back in the office, our group watches the camera set itself on the live monitor. We’re near the end of a long day, and Howard is suddenly back over by the group, checking in.

“Don’t feel bad if you need to close your eyes for a few minutes,” he says with a big smile, “George Lucas fell asleep while we were filming ‘American Graffiti’!”

And like that, he’s gone, back to work with his actors on the next shop, though he sends our way a PA with a big plate of brownies.

What a nice guy.

The Dilemma hits theaters on January 14, 2011. You can check out bigger versions of these new photos and more here, and stay tuned later this week for more interviews from the set!