Jack may never let go … of his bachelor status.

Leonardo DiCaprio, 38, has been living model-to-model for what feels like a couple of decades now. He takes plenty of risks with his film roles — like playing the Great Gatsby himself — but he seems entrenched in the Clooney zone in his real life. Leo previously told Esquire, "Six months of being on location or being off in Morocco or someplace like that, is not the best thing for a relationship."

He talked to Extra about how one of the tradeoffs for his fortunate career is having his personal life displayed on the public stage. "Oh that's always something that's synonymous with becoming an actor, but that's a conscious choice too," he said. "You know that if you're going to venture into this world your private life is going to become public. But like I said, you adapt to those circumstances."

He’s turning 39 this fall, and 40 is right around the corner. How does he feel about that? "I don't know, I feel better than ever." He laughed. "Am I supposed to feel bad about that?" Some people have a huge fear about that, but not him. Is he thinking the single life something he wants to give up at some point? Settle down, get married and have a family? "I take it as it comes," he told Extra. "We'll see what happens in the future. ... I don't try to determine what the future will be. I take it day by day."

In 2010, Leo sounded more sure about settling down, telling Le Matin, “Someday that’s absolutely gonna happen. Do I want to be a father? Yes, but I think I have a few more years. That said, I don’t think I need to have children to play a father in the movies. This feeling is in me, I understand it completely. In my private life, I still have time to become a dad, and I’ve no desire to rush.”

He's still pretty young, and there's no rule saying everyone HAS to get married and/or have kids. Female celebs get asked about it all the time, so it's only fair that Leo fields a few questions on that front too, but it's possible he'll just keep on keepin’ on — it never seems like he’s lonely for too long!

Sources: Extra, Huffington Post