Enrique Iglesias Reveals If He Feels 'Awkward' Singing 'Tonight (I'm F---in’ You)' Now That He's a Family Man (Exclusive)

Enrique Iglesias scored when he released his song "Tonight (I'm F---in' You)" in 2010 — but is it weird performing the hit now that he's a family man?

"No, not at all, actually!" he tells PEOPLE of the hit.

Iglesias, 48, adds: "I have thought about: OK, if I’m alive when I’m 60, 70, and for some crazy reason I happen to be touring, how is it going to sound when I’m singing 'Tonight I’m F---in’ You'? But I still haven’t gotten to that point where I’m like, 'Oh s---, I feel really awkward singing this song.'"

Iglesias — who shares twins Lucy and Nicholas, 5, and daughter Mary, 3, with longtime partner Anna Kournikova, 42 — is now on the road for The Trilogy Tour with pals Pitbull and Ricky Martin. The trio kicked off the tour in Washington, D.C., on Oct. 14 and will be on the road through Dec. 11.

Before he hit the road, Iglesias caught up with PEOPLE and discussed the stories behind some of his biggest hits, which have made him one of the best-selling Latin artists of all time, with 70 million records sold. See the breakdown below.

‘BAILAMOS’

When I did my first three albums, it was more ballad-driven love songs in Spanish. Then I did my first English song, “Bailamos,” back in 1999. I remember feeling not in my comfort zone, just because it was very different, and it was also in English. So even if I grew up in the U.S. singing in Spanish and in English, it’s so different how you write it.

That song to me was one of those life-changing moments in my career. Once it was finished, I was like, “Oh my God, I think this is what I was looking for.” I wasn’t even thinking about, “OK, this is going to take me to the next level of my career.” I needed it for me to just move on forward. And then from there, of course, the whole Latin explosion happens. A lot of journalists used to ask me, “What do you think about this Latin explosion?” I was like, “It’s not an explosion. This is here to stay.” I think now in 2023 we can say that’s pretty true. 

‘COULD I HAVE THIS KISS FOREVER’  (Feat. Whitney Houston)

The first time we met, I was just mesmerized. And I remember thinking, “I can’t believe I’m sitting here with Whitney Houston.” When I first moved to America, she was one of the artists that I would just listen to all the time. And the fact that I was still kind of a kid and I was in a video shoot or in a studio recording a song with Whitney Houston, I was like, “This is insane.”

‘HERO’

After “Bailamos,” I think everyone stereotyped me in a way. But I was thinking, “I can write a ballad in English the same way I used to write those songs in Spanish.” I remember writing “Hero” and having it there for a year and 10 months, which is a long time, and trying to convince the label, “Please, this was the song.” It wasn’t typical, because everybody thought first singles at the time had to be up-tempo. But I knew that it was one of those songs that when I wrote it, it just felt special. And once we filmed a video and the song went out, that was another tipping point. 

‘ESCAPE’

I wrote it with [songwriter] Kara DioGuardi. We were in the studio, and we were a little bit frustrated. We had basically lived in the studio for the past six months — sleeping in the studio every single day — trying to finish the album. We took a break, went outside to the parking lot, and Kara and I were just hanging out there eating donuts. And [producer Steve Morales] played a new track, and immediately Kara and I, just perfectly in sync, sang the melody.

We started writing the lyrics, and I’m not exaggerating: We probably did it in 10 minutes. It was that fast. It was super fast. We wrote it in the parking lot with the chorus, with the verse. And then the rest is history. “Escape” ended up being the second single, and that’s when I met Anna, in the video.

‘I LIKE IT’ (Feat. Pitbull)

I had “I Like It” for three years and was trying to convince the label that that was it. And they were like, “No, the dance thing is not happening.” Luckily I was able to change labels within the music company that I was with at the time, and when I played the song for the person that was in charge of that label, he was like, “This is a no-brainer. Let’s go for it.”

That was, to me, another tipping point in my career, because it was like, “Oh my God, there’s been a few years that maybe my music hasn’t connected so much in the U.S., and suddenly this song, which I believe in so much, connects.” Just because it was a fun fantasy — not overthought, just a fun song.

‘TONIGHT (I’M F---IN’ YOU)’ (Feat. Ludacris & DJ Frank E)

“Tonight (I’m F---in’ You)” was actually a demo that the label had sent me. I listened to it, and I was like, “Oh my God, this is a massive song. I need to record this song now.” And I never feel that urge, especially when it’s a song that I haven’t written. But to me it was a perfectly written song in the sense that when it got to the chorus, you didn’t pay so much attention to the F-word. I played it for a few people, and they were like, “Are you insane?” When I believe in something so much, I will just keep on fighting, fighting, fighting.

‘BAILANDO’  (Feat. Sean Paul, Descemer Bueno & Gente de Zona)

We wrote it here in my house in Miami, and right when we got to the “Bailando” [sings] part, I sang that, and it just came out naturally. Immediately I was like, “Ooh, maybe I shouldn’t say ‘bailando’ because I have a song called ‘Bailamos.’ ” But that was the songwriter within you. I thought, “Ah, whatever.” I knew that it was really good and really catchy, and it just made me feel happy.

Descemer [Bueno, a Cuban singer-songwriter] actually recorded it with his vocal, and he put it out online in Cuba. So a friend of mine calls me that happens to be in Cuba and says, “Man, I was in a taxicab, and I heard this song that is amazing.” I’m like, “What song is it?” And he finds the song, he puts it on speaker, and I go, “Dude, that’s my song. That’s a song that I wrote!”

For more on Enrique Iglesias, pick up the latest issue of PEOPLE, on newsstands everywhere Friday.