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KENNY CHESNEY

SUN-BLEACHED STRAW HAT? CHECK. TANNED TOES DIGGING INTO THE SAND OF A FLORIDA BEACH? CHECK. CUT-OFF T-SHIRT SHOWING OFF THOSE WELL-HONED BICEPS? CHECK AND OH, YES, DOUBLE CHECK.

It's a look that's helped make Kenny Chesney country's favorite beach boy and win him a string of Entertainer of the Year trophies - and the title of PEOPLE Country's Hottest Guy 2013. But while the person staring out at the water this morning looks like the same fast-forward-living superstar who's been selling out stadiums and racking up hit singles for more than a decade, the singer admits he doesn't feel the same. And there's an intensity and thoughtfulness about him that hints at a man who wants to dig a little deeper. "Sometimes things happen that just stop you in your tracks, and they change you," says Chesney, 45. "And that's what's happened to me. I'm a different person now."

For Chesney, it was the sudden death of longtime friend Kristi Hansen last year that made him take stock of his life. Hansen was part of a circle of friends he'd met back in the 1990s when he was just on the cusp of stardom and began spending his downtime in the U.S. Virgin Islands. "We came from all over and wound up there for our own different reasons," he says. "But they were all just like me. We were all a bunch of free spirits, all chasing something or running from something, and we all loved love and loved life and loved living it there."

Hansen's death from a brain aneurysm at age 35 - while six months pregnant with her first child - devastated the singer and inspired him to reevaluate his own life. "You realize it could all end in a second," he says. "And if it all went away just like that, did I do everything I wanted to do, did I say everything I wanted to say?"

Chesney admits he didn't like his own answers. "I mean, my life's been blessed, don't get me wrong - professionally it's been great," says the singer, who was briefly married in 2005. "But personally ... it hasn't always turned out the way I wanted it, and I haven't always been the person I wanted to be. I knew I needed to make some changes."

The spirit of those changes is evident on his latest album, Life on a Rock, which includes a tribute to Kristi called "Happy on the Hey Now" as well as what Chesney calls an "insanely personal" collection of songs about his life in the islands. "It's a bunch of postcards about my life and where I like to go when I'm not this person, this stadium Kenny," he says. That kind of openness doesn't come easily to the singer, "but I'm getting better at it," he says. "I'm getting more comfortable with being open and vulnerable, and I'm letting some of the walls come down. If you want that connection with your audience, you have to be honest."

He's also getting better at letting those already close to him come a little closer. "I think when you're constantly gone like I am, you sometimes take your family and friends for granted. You figure at some point you're going to come back and reconnect with them, but there's always something," he says.

Since Kristi's death, Chesney says he has been determined to reach out to those he loves. "I call my mom, my friends, people I haven't seen in a while or haven't talked to just to let them know I'm thinking about them," he says. "I try and tell people I love them a little more. I don't think anyone ever gets tired of hearing that."

And when he's with someone, he makes sure he's fully present. "For a long time I could have a conversation with someone and look straight over their head and never hear a word," he says. "I'd walk away and say, 'What the hell did we just talk about?' I don't want to be that person anymore. Now I look them in the eye and really talk to them and really hear them."

Chesney also credits Kristi with teaching him to live in the moment and take life as it comes. "Some people are good at math, some people are good at music. But Kristi was just really good at life," he says. "As busy as my life is, I don't stop and breathe a lot, and since she died, I do. I'm trying to get better at that. Just enjoying life in the moment and not trying to plan, which is hard for me."

This transformation has been good for his personal life: He's been dating girlfriend Mary Nolan since last fall. "I'm in a relationship, and it's a great one," he says. "It's going really well. I'm very happy." And he's content to live in that moment: "I want to let life come the way it wants to come and enjoy every day of it. A lot of times when I've tried to plan, it never works out the way I've planned it. So I try not to look too far ahead."

Instead he plans to concentrate on letting go of old regrets and being grateful for all the love in his life. "Life has a way of letting it all come out in the wash," he says. "What's gonna happen is gonna happen. I think that people that you meet - in friendships, relationships or whatever - those relationships have a way of finding their spot. I'm happy. And I'm trying really hard to enjoy the moment."