This interview was done in 2009, I recently came across the article and wanted to share!
Those who despair that the things on that fourth-grade “to-do-before-40” list—the moon landing, the marriage to Lyle Waggoner—might not come to fruition should probably put down this magazine and find a nice biography of Colonel Sanders or some other late bloomer. Here, we’re paying tribute to the accomplishments of fortieth-birthday boy Diddy, aka Sean Combs, the Harlem-born mogul who saw J.Lo naked well before Ben Affleck did; changed his name (three, four—eleven?—times); was acquitted of a felony; discovered, produced, and eulogized Biggie Smalls; and acted on Broadway, in movies, and even chewed some scenery alongside David Caruso on CSI Miami. He has launched a fashion label, a cologne, and a restaurant, and fathered six kids while somehow staying single. This birthday month brings another milestone, as Combs shares with ELLE his biggest fear: the dreaded long-toed lady.
ELLE: Were you a sexually precocious kid?
SEAN COMBS: I was in pursuit of female attention from when I was probably four or five. It started with my mother’s friends putting me to sleep on their laps. But I wasn’t really asleep; I was enjoying the way it felt to lay on a pair of beautiful breasts.
ELLE: And how did your first time go?
SC: Great, but I’d had a lot of practice from watching this show on cable called Midnight Blue, where they had actual scenes from pornos. Me and Midnight Blue had a Thursday night at one o’clock date—I’d make sure my mother was asleep, take a shower, lock the door, put on cologne.
ELLE: Wasn’t there an awful lot of talking from Midnight Blue host Al Goldstein?
SC: Yeah, he definitely talked a lot. And he interrupted. But it taught me mind control.
ELLE: Your dad was shot to death when you were only three. Who taught you how to behave with women?
SC: A couple years ago, my psychologist came to the conclusion that this is one of the big problems I have as far as maturing in a relationship. After my father got killed, my mother said, “I’m never getting married again. I don’t want men around my children.” So I’ve never actually been able to witness a husband and wife’s love. Sometimes when I see it with my friends, I just find myself staring like a child, because I’ve never actually seen it before. It’s one of the sad parts of my life.
ELLE: So what kind of behavior does this bring out in relationships?
SC: When a relationship gets to a certain point, I probably get scared and become a little self-destructive.
ELLE: By self-destructive, do you mean going out with other women?
ELLE: If you get caught cheating red-handed, what’s the best response?
SC: Cry. It might not work, but it at least shows that you care. Goddamn, this is a deep interview. You didn’t ask Will Smith none of this shit!
ELLE: But we’re making such valuable progress! Just tell me: Are the tears real?
SC: Yeah, it hurts me. One of my weaknesses is that I actually have a conscience.
ELLE: What’s the nicest thing your mother ever did for you?
SC: She sacrificed. My mother’s a beautiful woman and could have been in a relationship to help out with the bills. She didn’t want to go that route, so she worked four jobs and sacrificed a lot—dresses or shoes she might have bought—for me.
ELLE: Do you feel any guilt about that now?
SC: My mother’s no dummy. She taught the lesson about sacrificing for your kids, but also that if your kids hit it big, they better make it up to you for those years. She’s gotten her sacrifices back with interest.
ELLE: What’s the most extravagant gift you’ve given your mom?
SC: The house she’s in now.
ELLE: So you bought her, what, a nice split-level with an attached garage?
SC: Nah, nah, nah. We’re talking about something behind some gates. Like I said, she’s making up for it.
ELLE: Before he married Demi Moore, Ashton Kutcher once suggested to me that some mindblowingly debauched sexual stuff went on while he was hanging with you—it seemed to involve having sex with women while in the same room. What’s your rule of thumb about that?
SC: It’s fine if it’s your homeboy and you’re not brushing up against each other. And as long as there are two girls in the room.
ELLE: Naturally. In 2006, your net worth was estimated at almost $350 million.
How much would you require to deposit your sexuality in a lockbox for a year?
SC: If you gave me a billion dollars, you could lock my shit up for a year and two weeks. If it’s untaxable.
ELLE: Generally, who says “I love you” first, you or the woman you’re with?
SC: Me. I’m just a helpless romantic.
ELLE: What’s your speed record from meeting to saying “I love you”?
SC: Two seconds. I once saw this girl, and it just came out. And I meant it. Then she’s like, “You do?” And I’m like, “Yeah, I really do. Do you believe me?” And she’s like, “The way you said it, I believe you.”
ELLE: So? So? What happened?
SC: I went on two dates with her and realized I didn’t love her.
ELLE: I’ve heard that you have high foot standards for women. True?
SC: People are too loose with feet. When I look down, I don’t want toes hanging over the front of the shoe, looking extra long.
ELLE: So, what if a beautiful woman has a six-inch-long middle toe but it is tucked into a nice pair of custom-made shoes?
SC: I don’t care if she’s Charlize Theron. I’m definitely not messing with any woman with a six-inch-long middle toe.
ELLE: If my wife was so obsessed with you that she refused to have sex with me, what fact about you might cool her emotions?
SC: I don’t know. I think your wife would have a good time with me. I think you’re just going to have to make up a lie.