Donald Trump’s Timeless Wisdom on Love

The Fairer Sex

Trump’s always been something of a sexist feminist. Women! Just the best! Really something! Who knew they could be smart and beautiful and just as vicious as men!

An embroidered heart that reads “I like a woman that’s a little chubby,” a quote from Donald Trump.

“Part of the problem I’ve had with women has been in having to compare them to my incredible mother, Mary Trump. My mother is smart as hell.”

The Art of the Comeback, 1997

“I think that the woman’s sex drive is actually as good or greater than a man’s sex drive. … I’ve been witness to it and perhaps you have—if you’re lucky.”

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“Without women, there is nothing.”

TrumpNation: The Art of Being the Donald by Tim O’Brien, 2005

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“I love looking at models. … Isn’t that disgusting? The women here are going to walk out saying, ‘Isn’t that guy a terrible, terrible barbarian.’”

Palm Beach Post, November 26, 2001

“But I don’t think all women are gold diggers. There’s nothing more beautiful to me than a woman. I love and respect them. I’ve known a lot of really good women and have had amazing relationships over the years. But as with men, there are good ones and bad ones.”

Playboy, October 1, 2004

“I like a woman that’s a little chubby.”

— The Howard Stern Show, December 15, 2004

A doily with a quote by Donald Trump that reads, “The only time you want your chick to have acne is if it's because she's a teenager.”

“The only time you want your chick to have acne is if it’s because she’s a teenager.”

— The Howard Stern Show, December 7, 2005

“Women have one of the great acts of all time. The smart ones act very feminine and needy, but inside they are real killers. The person who came up with the expression ‘the weaker sex’ was either very naïve or had to be kidding. I have seen women manipulate men with just a twitch of their eye—or perhaps another body part.”

“There’s nothing I love more than women, but they’re really a lot different than portrayed. They are far worse than men, far more aggressive, and boy, can they be smart. Let’s give credit where credit is due, and let’s salute women for their tremendous power, which most men are afraid to admit they have.”

An embroidered quote from Donald Trump that reads, “Women are far stronger than men. Their sex drive makes us look like babies. Some women try to portray themselves as being of the weaker sex, but don’t believe it for a minute.”

“Women are far stronger than men. Their sex drive makes us look like babies. Some women try to portray themselves as being of the weaker sex, but don’t believe it for a minute.”

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“I don’t know why, but I seem to bring out either the best or worst in women.”

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“Ivana was gorgeous, but she was also ambitious and intelligent. … I found the combination of beauty and brains almost unbelievable. I suppose I was a little naïve, and perhaps, like a lot of men, I had been taught by Hollywood that one woman couldn’t have both.”

Trump: Surviving at the Top, 1990

“You’re not allowed to use the word beautiful anymore when you talk about women, you’re not allowed, no no. It’s politically incorrect … I will never call a woman beautiful again, and every man here—every man here, raise your hand, you will never, ever say your wife, your girlfriend, anybody is beautiful, right?”

— Rally in Cleveland, Ohio, November 5, 2018

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In the ’70s, on Manhattan’s Upper East Side, Trump was at a crowded nighttime hotspot and tapped on the shoulder of the woman who would become his first wife. He could, he said, help her and her friends get a table. “I’m very friendly with the owner.” The next day, she received three dozen roses. A few decades later, of course, his manner of pursuit could be a little different.

A cross stitched Donald Trump with a quote by him that reads, “I’m a major romantic.”

“I’m a major romantic.”

— The Howard Stern Show, February 27, 2013

“Sometimes you decide immediately—love at first sight. Sometimes you go slowly—the long engagement. … Sometimes you’ll think with your head. Other times you’ll think with other parts of your body, and that’s good.”

Trump: Think Like a Billionaire, 2004

“I think the big thing is you have to find somebody that you have chemistry with. Prior to my marriage, I would go out with a woman that was very beautiful, but if there was no chemistry, no matter what I did, then it just wasn’t going to work.”

Think Big and Kick Ass in Business and Life, 2007

“I’m very busy to be running out looking for presents.”

A quote by Donald Trump, next to a palm tree, that reads: “Dating is like being in Vietnam.It’s like war out there.”

“Dating is like being in Vietnam…It’s like war out there.”

— The Howard Stern Show, January 11, 1993

“I only have one regret in the women department—that I never had the opportunity to court Lady Diana Spencer. I met her on a number of occasions. I couldn’t help but notice how she moved people. She lit up the room with her charm, her presence. She was a genuine princess—a dream lady. She’ll be truly missed.”

“I watched @todayshow this AM re: @MarthaStewart & dating. She looks terrific, better than ever, any guy would be lucky to be with her.”

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“People are really vicious, and no place are they more vicious than in their relationships with the opposite sex.”

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“It’s all in the hunt and once you get it, it loses some of its energy. I think competitive, successful men feel that way about women. Don’t you agree?”

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Credit, indeed, where credit is due: Trump just marked 15 years of marriage to the former Melania Knauss. The guest list for their lavish Palm Beach nuptials included Shaquille O’Neal, Sylvester Stallone, Oprah Winfrey, Hillary Clinton and Rudy Giuliani. “I’m gonna be a very good husband for a change,” Trump told Billy Bush.

A embroidered pillowcase, with a quote by Donald Trump, that reads: “Marriage is, like, really great. It usually doesn’t work.”

“Marriage is, like, really great … I don’t know if it’s security or whatever it is, but I think it’s good. If it works. I mean if it doesn’t work, it’s a total catastrophe. It usually doesn’t work.”

— The Howard Stern Show, December 15, 2004

“Having a good wife and having a nice family is very, very important. There is no substitute for it, frankly.”

— Interview with Rona Barrett, 1980

“I never speak about my wife—which is one of the advantages of not being a politician. My marriage is and should be a personal thing.”

Playboy, March 1, 1990

“I believe in marriage—one woman, one marriage.”

— ABC Primetime Live, March 10, 1994

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“I love the institution of marriage. It cost me a fortune, but I love the institution of marriage.”

— Late Show with David Letterman, August 21, 1997

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“My nine-to-five day fascinated and energized me. But then, late in the afternoon, I’d often get a call from Ivana, reminding me of that night’s engagement … Sometimes I’d get angry and say I wasn’t going, and we’d fight about it on the phone. In the end, because I didn’t want to disappoint or embarrass her, I’d almost always agree to go along. When I hung up the phone, though, I’d often say, loud enough, I suppose, for anyone standing in the hall outside my office to hear me, ‘My life is shit.’”

“Congratulations to Michelle and Barack Obama on their 20th anniversary.”

— Twitter, October 4, 2012

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“Happy Anniversary to my wonderful wife @MELANIATRUMP — a truly great decision by me!”

— Twitter, January 22, 2014

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“@katyperry Katy, what the hell were you thinking when you married loser Russell Brand. There is a guy who has got nothing going, a waste!”

— Twitter, October 16, 2014

“I always felt that if you have to work at a relationship that the relationship is not going to work.”

“Marriage is a contract unlike any other contract in life. You marry for love. But your signature on the marriage certificate is all about rights, duties, and property. It’s a legally binding contract that knows nothing of love.”

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“One thing I have learned: There is high maintenance. There is low maintenance. I want no maintenance.”

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“Marla was always wanting me to spend more time with her. ‘Why can’t you be home at five o’clock like other husbands?’ she would ask. Sometimes, when I was in the wrong mood, I would give a very materialistic answer. ‘Look, I like working. You don’t mind traveling around in beautiful helicopters and airplanes, and you don’t mind living at the top of Trump Tower, or at Mar-a-Lago, or traveling to the best hotels, or shopping in the best stores and never having to worry about money, do you? If you want me to be home at five o’clock, maybe these other things wouldn’t happen and you’d be complaining about that, too. Why would you want to take something that I enjoy and change it?’ I always viewed her whys as being very selfish. But the fact is, in a marriage both sides have to be happy. If they’re not, it’s just not going to work.”

“Find a woman who is supportive, because there is nothing better than a supportive woman.”

“A good marriage is like negotiating an important deal: You have to consider all the factors, thoughtfully and thoroughly … I don’t approach it any more haphazardly than I do a very important deal. In fact, considering the amount of deals I’ve made compared to the number of marriages I’ve had, I’d say I’m quite cautious about marriage. You should be, too.”

“Being on the other side of a relationship with someone like me must be difficult.”

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Trump has cheated on his wives when he feels like he’s riding a high—Marla Maples in 1988, for instance, or Stormy Daniels, allegedly, in 2006. Trump, obviously, always has maintained total discretion.

A quote by Donald Trump surrounded by flowers that reads, “Beautiful, successful, married—I’ve had them all, secretly, the world’s biggest names, but unlike Geraldo, I don’t talk about it.”

“Geraldo Rivera is a friend of mine, but he did something which I thought was absolutely terrible and he admits it was a mistake. He wrote a book naming many of the famous women that he slept with. I would never do that—I have too much respect for women in general, but if I did, the world would take serious notice. Beautiful, famous, successful, married—I’ve had them all, secretly, the world’s biggest names, but unlike Geraldo I don’t talk about it.”

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“There are those that say that you’re more attractive after you get married.”

— The Howard Stern Show,  December 15, 2004

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“I remember attending a magnificent dinner being given by one of the most admired people in the world. I was seated next to a lady of great social pedigree and wealth. Her husband was sitting on the other side of the table, and we were having a very nice but extremely straight conversation. All of a sudden I felt her hand on my knee, then on my leg. She started petting me in all different ways. I looked at her and asked, ‘Is everything all right?’ I didn’t want to make a scene in a ballroom full of five hundred VIPs. The amazing part about her was who she was—one of the biggest of the big. She then asked me to dance, and I accepted. While we were dancing she became very aggressive, and I said, ‘Look, we have a problem. Your husband is sitting at that table, and so is my wife.’ ‘Donald,’ she said, ‘I don’t care. I just don’t care. I have to have you, and I have to have you now.’ I told her that I’d call her, but she had to stop the behavior immediately. She made me promise, and I did. When I called I just called to say hello, and that was the end of that. But the level of aggression was unbelievable.”

“When a man leaves a woman, especially when it was perceived that he has left for a piece of ass—a good one!—there are 50 percent of the population who will love the woman who was left.”

Vanity Fair, September 1990

A crossstitch of Donald Trump in bed with a woman, with the quote on the sheets saying “I’ve never had any bed.”

“I’ve never had any trouble in bed …”

“… it happens all the time. One woman, who was also socially prominent, was getting married, and I had bumped into her on Fifth Avenue while she was exchanging wedding gifts. I had my limousine nearby, and she asked if I could give her a ride back to her apartment on Park Avenue. I said absolutely, not even suspecting that within five seconds after the door closed she would be jumping on top of me wanting to get screwed. I said, ‘You’re getting married next week, and I’m going to your wedding.’ ‘I don’t really care,’ she said. ‘I never liked him that much anyway, and you know that.’ I was really in a quandary, because she is a truly great-looking and sexy woman.”

“I even thought, briefly, about approaching Ivana with the idea of an ‘open marriage.’ But I realized there was something hypocritical and tawdry about such an arrangement that neither of us could live with—especially Ivana. She’s too much of a lady.”

“Robert Pattinson should not take back Kristen Stewart. She cheated on him like a dog & will do it again–just watch. He can do much better!”

— Twitter, October 17, 2012

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“Everyone knows I am right that Robert Pattinson should dump Kristen Stewart. In a couple of years, he will thank me. Be smart, Robert.”

— Twitter, October 22, 2012

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“You know what I hate? When I see a woman and a man married, and a woman is married to a rich guy, right? And then the guy kicks the bucket. He’s gone, and she’s dating the following week.”

— The Howard Stern Show, July 16, 2008

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“The divorce from Ivana taught him a great lesson,” the late Liz Smith, the longtime gossip columnist, told the makers of the documentary, Trump: An American Dream. “He proved then he couldn’t have his reputation destroyed. He learned he could ultimately get away with anything.”

A quote by Donald Trump, surrounded by candy hearts, that reads “What the hell do I know, I’ve been divorced twice?”

“It’s a terrible document. It’s ugly, it’s—it’s horrible in almost every way, but you need it. It’s very tough to walk up to a woman or a man and say, ‘Listen, darling, I love you very much, but just in case we get divorced, this is what you’re gonna be getting, if it’s OK with you.’”

— CBS This Morning, January 9, 1998

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“I hate the concept of divorce. I hate everything it represents.”

— Larry King Show, April 18, 1990

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“I have a friend who’s a professional golfer, he’s married. He could be a very good player. Every night he gets a call from his wife, ‘Why aren’t you home? … Why are you in North Carolina. Why are you in California?’ He plays the tour. ‘This is what I do because I’m a touring professional.’ ‘Well, why don’t you become a home professional?’ ‘Well, you know, because it’s not quite as much money since I’m a touring professional. I’m a great golfer, I have a chance to be a really great golfer.’ Every night she calls up crying and bitching, and I said to him: ‘Get a divorce, cause you never gonna change her.’”

— The Howard Stern Show, November 4, 1997

“Often, I will tell friends whose wives are constantly nagging them about this or that that they’re better off leaving and cutting their losses. I’m not a great believer in always trying to work things out …”

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“You know, you look at divorce rates, the biggest problem with marriage and the biggest reason for divorce is money. They don’t have enough money.”

— Speech at the National Achiever’s Congress in Sydney, Australia, September 21, 2011

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“You were in love with somebody, and now you are no longer in love. The hatred is so intense, far more intense than it usually gets in a business transaction. There is nothing more vicious than a man or woman going through a divorce. It is pure hell, like nothing else I have ever seen.”

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“I hope Mark Zuckerberg signs a prenup with his current girlfriend- perhaps soon to be wife. Otherwise, she can walk away with 9 billion.”

— Twitter, May 15, 2012

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“Anybody of wealth or even modest wealth who doesn’t have a prenuptial agreement is mentally retarded, okay?”

“My comeback would have been totally impossible had I not had fully executed and well-drawn prenuptial agreements with both Ivana and Marla.”

“I recently played golf with one of the most brilliant men on Wall Street, the head of Morgan Stanley, John Mack. John is a good friend of mine who is married to a fabulous woman. Christy is totally supportive of the long, hard hours he works. John was telling me that after our game he was going to see one of his men. This particular man had the potential to be a star at Morgan Stanley, but he was having tremendous difficulty with his wife. She always complained that he was working too hard and too long and wasn’t devoting enough time or energy to her. Without any further discussion, I looked at John and said, ‘Tell the man to lose the wife. There is no hope for that marriage. Tell him if he stays, he’ll do a lousy job for you.’ … I told John that I didn’t want to sound cold or cynical, but I knew the marriage just wasn’t going to work. If the woman was inclined this way, she was not going to change. I actually told John to pull the young man aside and tell him that it was me who made this recommendation: If he doesn’t lose the ballbreaker, his career will go nowhere.”

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“Everyone goes into a marriage thinking that it will last forever. But over fifty percent of the time, marriages don’t work out.”

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“You should never ignore the power that money has to destroy relationships.”

“What the hell do I know, I’ve been divorced twice?”

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