1. Looks are important, but so is intelligence
Trump has dated and been married to the most beautiful women in the world: Anna Nicole Smith, Carla Bruni, Marla Maples (his second wife), and current wife Melania Trump, just to name a few. However, it was his first wife Ivana that taught him that beauty and brains are the winning combination:
I knew from the start that Ivana was different from just about all of the other women I’d been spending time with. Good looks had been my top — and sometimes, to be honest, my only — priority in my man-about-town days. Ivana was gorgeous, but she was also ambitious and intelligent. When I introduced her to friends and associates, I said, ‘Believe me. This one’s different.’ Everyone knew what I meant, and I think everyone sensed that I found the combination of beauty and brains almost unbelievable. I suppose I was a little naive, 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
2. You both have to want the same things
One of the most important things Trump will tell you is that a good relationship involves being on the same page and wanting the same things. You both have to agree upon each of your lifestyles and be accepting of the other, because without that, the relationship is inevitably doomed. Trump speaks about this as being the main reason why his second marriage to Marla Maples ended:
My marriage to Marla lasted three and a half years. Sadly, like so many couples these days, we drifted apart. Our lifestyles became less and less compatible. We wanted different things. Marla was content when it was just her, [their daughter] Tiffany, and me. I, on the other hand, realized that business needed to be taken care of constantly. When two people have such a difference in opinion regarding the lifestyle they want to lead, there is no longer any reason to stay together.
– Trump: The Art of the Comeback
3. Keep business out of marriage
Don’t work with your significant other. It can be a very sticky thing to get involved with, and it’s incredibly difficult to maintain a sane relationship when you both work and play together. It’s not the healthiest combination, especially if work overtakes everything in the relationship and becomes the basis for every conversation. Trump learned from his first marriage to Ivana that handing over part of his business to her was not the smartest move for their marriage:
My big mistake with Ivana was taking her out of the role of wife and allowing her to run one of my casinos in Atlantic City, then the Plaza Hotel. The problem was, work was all she wanted to talk about. When I got home at night, rather than talking about the softer subjects of life, she wanted to tell me how well the Plaza was doing, or what a great day the casino had. I really appreciated all her efforts, but it was just too much. . . I will never again give a wife responsibility within my business. Ivana worked very hard, and I appreciated the effort, but I soon began to realize that I was married to a businessperson rather than a wife.
– Trump: The Art of the Comeback
4. You either bring out the best or worst in someone
This happens to be a huge indicator in knowing whether a relationship is right. When a relationship is right, you tend to bring out the best in each other. When it’s wrong, the opposite is true. Trump plainly realized this with a lot of the women he dated, which one can surmise is why the relationships probably never worked out. Trump reveals in his book, Trump: The Art of the Comeback: “I don’t know why, but I seem to bring out either the best or worst in women.”