Ray Romano Ray Romano

Men of a Certain Age turns 2 — the so-called "terrible" stage in life — on Monday. But for the TNT drama, things remain as bittersweet as ever for its leading men as they continue to tackle and tiptoe around middle age.

"It's kind of that never-ending arc that everyone has in life, where you're still trying to get out from under," Ray Romano tells TVGuide.com. "They have a destination they want to get to, but they never really get there or are just trying to improve themselves. Sometimes it gets a little hairy, which it does this year, and sometimes it gets a little nice."

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Season 2 finds pals Joe (Romano), Owen (Andre Braugher

) and Terry (Scott Bakula) facing new challenges. Newly divorced Joe has kicked his gambling habit and hopes to join a senior golf tour; Owen is attempting to assert himself in his new power position at his dad's car dealership; and womanizing actor Terry is trying to sell cars at the same dealership at the expense of his ego. But just as they begin their respective fresh starts, life keeps testing them with more twists and turns."It'd be disingenuous to say that their issues went away because something changed," says Romano, who created the show with Mike Royce. "You can't just do it in one week and the next episode, those demons are gone. They do do that [on other shows], but it's not reality. They're all intertwined. Joe's trying to motivate himself with the golf. His discipline isn't the best, but if he doesn't give it a shot, it will always be that missing piece. But he's still trying to rid himself of gambling."Compounding Joe's struggle is a run-in with his bookie, Manfro (Jon Manfrellotti), who's also now his neighbor, and Joe's own method of self-treatment. He tests his will power by making "mind game bets," i.e. no sweets for a week if he can't hit 100 yards on the green. "They seem innocent enough," the Everybody Loves Raymond alum says. "It's like using maybe alcohol to cure your drug addiction. Put it this way: There's still something going on there. He's still a little compulsive."

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And maybe impulsive when it concerns the matters of the heart? Joe hooks up with Michelle (Alanna Ubach), the woman he met in a hotel last season, for what the comedian calls a physical relationship. "I don't want to say it's empty, but he thinks this is what he needs now because he just got out of a big relationship. He doesn't necessarily think he belongs with her forever."Owen and Terry, meanwhile, just want to fit in — at the dealership. After finally getting the nod from his domineering dad to run the dealership last season, Owen is faced with a dismissive sales team that scoffs at the nepotism. That same team taunts newbie salesman Terry, who feels even more washed-up after the sales guys pull up an embarrassing '80s commercial of his on YouTube."Terry has kind of what Joe has — he never really fulfilled what he wanted to do. But should he be selling cars now?" Romano says. "It's as problematic for Owen since they're friends. He's trying to establish himself, come out his dad's shadow. It's complicated. He runs into a whole bunch of trouble."Such midlife complications of men, captured with pathos, honesty and humor, made the series a quiet hit among TNT's procedural-heavy lineup last year — not to mention demonstrate that Romano, who turns 53 on Dec. 21, excels at drama as much as he does at comedy. The critically acclaimed first season averaged 4.2 million viewers and Braugher nabbed a surprise Emmy nomination for drama supporting actor.

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"I think the tone was unexpected," Romano says. "Mike and I knew that everybody, no matter where you are in life, feels this limbo, so whether you talk about it or not, you'll identify with it. I don't want to paint a picture that everybody our age is in this mode, but there are failures and successes, and it's a bit of a struggle."But middle age and a midlife crisis are just stages in life. That's why, at least for now, Men will be halfway done after Season 2 wraps."I'm the one who insisted on four years and then I'll feel it out. But we also only insisted on 10 episodes a season and they've talked us into 12 this season!" Romano says. "I don't want to overstay our welcome. I still want to be passionate about it and enjoy it. I did realize one thing when Raymond ended: I think I need to do something. Financially, I didn't need another job, but spiritually, I needed one."Season 2 of Men of a Certain Age premieres Monday at 10/9c on TNT.