Here’s How 50 Famous Men Wooed the Women of Their Dreams
"I literally saw her across a crowded room. Literally."
There’s no one right approach to meeting a woman—every guy goes about it his own way, and the correct method for you will be what’s feeling right for you and your special someone in the moment. But if you’re in the market for a little inspiration, here we’ve compiled how 50 ultra-successful men—actors, athletes, and business leaders—wooed and won the women of their dreams. So read on, and take notes! And once you’ve hit it off with her, you’ll need to hold onto her—so be sure to read the 40 Secrets of Couples Who’ve Been Married 40 Years.
When it came to romancing his now-fiancée, Meghan Markle, Prince Harry pulled out all the stops. After being set up with her through a friend, he sent her a forest of flowers, he shut down the Natural History Museum for a private after-hours tour, and he whisked her away as a plus-one to a tropical destination wedding. Beats the stuffing out of, “Drinks Thursday?” And for more on how Harry played the romance game, check out the 10 Princely Ways Harry Won Meghan.
“I did it the old-fashioned way—by telephone,” Timberlake told Pop Sugar about wooing Jessica Biel. “The way I see it, if you’re asking a girl out on a date, it’s only right to do it in a way that she can hear your voice. I had to be pretty persistent in order to get her to say yes. But I have a fair amount of tenacity and if I want something I stick to it. And in the end she agreed.” If you’re looking to woo someone of your own, you may want to check out the 50 Pick-Ups Lines So Bad They Just Might Work.
“The best thing that happened to me is in 1996,” McGraw said about connecting with his wife of 20 years, Faith Hill, as the two were preparing for their latest joint tour. “I had a really hot chick on the road with me! I fought and I fought and I fought to stay away from her, as long as I could. And that lasted about as long as her job at McDonald’s.”
“This friend told me he knew a girl version of me,” Brady said in Details magazine’s July 2009 issue. Gisele Bündchen, from the sidelines, added: “And he said to me he’d found a boy version of me.” He took Bündchen to dinner in New York City for their first date and things apparently went well. If you want to be a little more creative than dinner, however, try out any of the 40 Irresistible First Dates That Will Guarantee You A Second.
“We were just beginning to try to date each other,” Jay-Z told Vanity Fair. “Well, you know, you’ve got to try first. You got to dazzle…wine and dine.” He told her that “of course” he pursued Beyoncé—and when asked if he hadn’t been as high-profile as he is would he have been able to date her, he said, “If I’m as cool as I am, yes. But she’s a charming Southern girl, you know, she’s not impressed.…But I would have definitely had to be this cool.” And for more life lessons from America’s favorite rapper and mogul, here are Jay-Z’s 8 Best Life Tips.
“We were buddies then. I remember it was funny because for about a year after Green Lantern had come and gone and all that stuff we were both single,” he said about Blake Lively on Entertainment Weekly’s Sirius FM show. “We went on a double date. She was on a date with another guy and I was on a date with another girl. That was the most awkward date for their respective probably because we were just like fireworks coming across,” Reynolds added, laughing. “It was weird at first but we were buddies for a long time. I think it’s the best way to have a relationship is to start as friends.” For more on Hollywood’s favorite funny-man, make sure to watch The Most Underrated Ryan Reynolds Movies of All Time.
“I was severely hungover,” Russell told Conan O’Brien of when he saw Goldie Hawn on the set of Swing Shift after having worked together 17 years before. “I just didn’t have in my mind what I was going to see. She had a great body, and so the first that came out was ‘Man, you’ve got a great figure.’ It kind of came out quickly, and it could’ve been wrong, and she said, ‘Why, thank you.'” Also, did you know Kurt Russell is one of the 12 Most Famous Actors You Forgot Were Once Famous Athletes?
“I had just gotten out of a pretty long relationship, so I was in no way ready for another,” Tatum told Elle about connecting with his then—Step Up costar Jenna Dewan. “I was trying to run from what I knew Jenna was—not someone I was just going to date. But one of my buddies was like, ‘What are you doing, man? She’s dope.’ That night I showed up at her hotel room with a sombrero on, and that was it…we were drinking at a Mexican joint and I stole [the sombrero] off the wall.” And for more celeb news, here are the 20 Craziest Celebrity Rumors of All Time.
“[It was] really nice,” Malik told the Evening Standard of the night he asked out Gigi Hadid—at a Victoria’s Secret party, followed by a first date to the Bowery Hotel’s Gemma restaurant. “She’s a very intelligent woman. She knows how to carry herself. She’s quite classy and that. She’s not, like, arrogant in any way, she’s confident. She carries it well. She’s cool.” And for more great relationship advice, here are the 30 Things Only Divorced People Know.
“We were texting a lot, and I started to see her sense of humor,” he told Harper’s Bazaar about wooing Chrissy Teigen. “We would talk on the phone, and I just started to fall in love with how engaging and witty and funny she is. And I think that’s when I really started to know that this was the kind of person I wanted to around a lot. Once we started spending more time together between tour stops and all this other stuff, we realized we had such a connection—and then it blossomed into a marriage and a baby!”
“I knew fairly quickly that I wanted to spend the rest of my life with Amal [but] we had never talked about it so there wasn’t like a ‘Hey, maybe we should get married,’” Clooney told Marie Claire. “Literally, I dropped it on her. And she just kept saying, ‘Oh my God,’ and ‘Wow’—completely unexpected. We just sat there and finally I said, ‘Listen, I’m 52 and I’ve been on my knee now for about 28 minutes, so I gotta get an answer out of this or I’m going to throw a hip out. I might not be able to stand back up.’” And for more relationship advice from America’s favorite former bachelor, check out the 30 Best Celebrity Relationship Quotes.
“I was messing up! I had practiced it so many times in my bathroom, I had my suit, my jacket on, and I was pulling the ring out, and everything was perfect,” he told Us Weekly about his proposal to Kayla Rae Reid. “Then when it actually happened I couldn’t get the ring out of my pocket and I was stumbling over all of my words! I was just so clammy and nervous—but then I finally got the courage to ask, ‘Will you marry me?’ And she said yes! And I was like, ‘Yeah! My life is complete!’”
“So I’m healthily single at a club on Sunset [Boulevard]. I’m not even a club guy, but I was a club guy. And I’m making margaritas at the end of the table, and this figure moves across the room,” he told Howard Stern about his future wife Camila Alves. “And I remember [saying] to myself, ‘What is that?’ I didn’t say, ‘Who is that,’ I said, ‘What is that?’ She sits down, and I can’t get my eyes off her, and I’m waving, trying to get her [attention].… I go over and introduce myself…And I go, ‘Would you and your friends like to come over and have a drink?’ She came by herself. Now we sit down, music’s playing. I make a margarita. That night I spoke 25 minutes of the best Spanish I’ve ever spoken in my life. So we go back to the house and continue the party for a while to extend the time. I’m trying to extend the time. And now she’s like, ‘OK, I’m gonna go. I’m gonna get a cab.’ And I’m like, ‘Don’t do that. It’s way too late. Take the guest bedroom.’” She agreed, happily for McConaughey. For more life tips from Mr. “Just Keep Livin” himself, check out the 20 Secrets of Ageless Celebrities.
“She walked into the bar where I was a really [bad] bartender, and it was kismet,” he told Martha Stewart Weddings. “After that I saw her every day for six months.”
“I remember seeing pictures of her and Paris Hilton in Australia, and I came to Don C., and I was like, ‘Man, have you ever seen Kim Kar-dijon? What’s up with Kim Kar-dijon?'” he told Ryan Seacrest in an interview about seeing a photo of Kim Kardashian with Paris Hilton in 2006.
The two crossed paths for years after that at various fashion shows and celebrity events, and by 2012 Kanye was singing about his infatuation in the song “Cold”: “And I’ll admit, I had fell in love with Kim/Around the same time she had fell in love with hiiiim/Well that’s cool, baby girl, do ya thang/Lucky I ain’t had Jay drop him from the team.” Instead of being creeped out by his attention, Kardashian soon reciprocated.
“I had a huge crush on her,” the actor said of Emma Roberts. “tried to be cool and funny and flirt a little bit, but it didn’t go over very well because I was just saying the wrong things, basically.”
“I was slow to make any moves because of our age difference, and also because she was a fan,” he said of Amber Tamblyn at a live comedy show in New York. “I took the opportunity to say, ‘Hey, this is our song.’”
“I had an elaborate plan that kind of folded in on itself, so I did it the old-fashioned way: We took our dog for a walk, and I had the ring tucked into my waist because I didn’t want it to bulge out of my pocket,” he told Harper’s Bazaar of his proposal to Elizabeth Jae Byrd. “There was no way I was taking that ring out of the box until it was on her finger—that’s the scariest thing, as a guy, is having that ring in your possession. You’re like, ‘When am I going to lose this?’ Because, personally, I lose everything. So we were on a walk with the dog at sunset, and I just got down on a knee.”
“[Ciara] was on tour, and I was looking at her in the mirror, and God spoke to me,” the devout NFL star said of his courtship of singer Ciara. “He said, ‘I need you to lead her.’ I told her, ‘What would you do if we took all that extra stuff off the table, and just did it Jesus’ way?'” She agreed, and he added, “I ain’t gonna lie to y’all now—I need you to pray for us. I know y’all have seen her on the screen. If there’s a 10, she’s a 15.” And if you’re still on the market these days, allow us to help you out: Here are the 40 Best Dating Tips for Men Over 40.
“I think she was in love with me at first sight and just doesn’t want to admit it,” the Dancing with the Stars pro joked to People about his fiancée and costar Petra Murgatroyd. “No, I walked in the way I walk in and … it’s just a lot of presence.”
“Oh, boy. She has that feistiness,” Bardem told The Daily Mail of when he considered dating Penelope Cruz. “There are those scenes where we are arguing, she’s throwing plates and so on. I had to wonder, ‘Do I really want this?’ She has what I call the loving blood. Passion for everything.”
“We were supposed to shoot in Hawaii, and then the movie got moved to Miami. I had never really hung out in Miami. I literally saw her across a crowded room, literally,” Damon told Vogue of seeing his wife Luciana Barroso for the first time. “Eight years and four kids later, that’s my life. I don’t know how else our paths would’ve crossed if that didn’t happen. If all those things didn’t happen.”
“I never really thought I would be married,” the actor told Just Jared. “Not that I was against it, my parents were married all the way up until my dad died, but I think I’ve always felt like that was something that more straight-laced people do. But then I met Persia [White] and she’s wild, interesting, passionate, fiery, and amazing. So I thought, ‘Alright, if it’s with her, that’s alright. I could do that.’ ‘Cause it’s still kind of this, eye of the hurricane thing, which is amazing.”
Speaking about his hyperbaric chamber on Jimmy Kimmel Live!, in which “you zip yourself into and it’s connected to an oxygen concentrator,” the actor described how “I put Nikki [Reed] in it on our second date…. All I’m saying is 10 months to the day, we were married.”
“First time I saw her, she was more beautiful in person than on TV,” the hockey player says of meeting his girlfriend, country star Carrie Underwood. “Obviously it’s tough with our schedules to see each other…. But we always find a way to make it work.”
“I was really nervous and that was my moment of truth,” he told Us Magazine about the first time he talked to Black Eyed Peas singer Fergie. “I laid out my outfit the night before. It was a big build to the moment that I could finally talk to her. And all I could say was, ‘You’re hot.'”
“I thought, she seems like a great girl—smart and funny and all those things that are so hard to find,” he says of meeting Kimberly Williams. “It felt natural to ask her to be in it. Even though I didn’t know if she was married, divorced, or just out of rehab. I really said to myself, ‘This time I’m not going to play games. I’m not going to pretend I’m somebody else, or do things I won’t be proud of later.’ I didn’t use my evil powers!”
“The connection there [between us], that was kind of rare. The hang was easy,” he told Good Housekeeping of connecting with his now-wife Amy Grant. “The conversation was easy.”
“We met at a hotel restaurant,” Washington told Oprah of meeting his wife, Pauletta. “I was just arriving to start work on the film Wilma [the 1977 television film biography of track legend Wilma Rudolph], and it was her last day of shooting. We met, but then we saw each other again at a party a year later. People who say they knew right away are lying! It’s a marathon, not a sprint.”
“We have such different backgrounds, it’s comical,” Shepard told Good Housekeeping of meeting Kristen Bell. “Until I was 32, I thought the world was just wolves, that there was no way anyone was acting with any kind of benevolence. When I met her and her friends, I was suspicious of their unbridled happiness. I thought, ‘Something stinks here; they’re in a cult.’ But slowly I began to see her positive way of looking at the world. She gives people the benefit of the doubt.”
“It should be a surprise for any woman … She was surprised,” the NBA star said of his proposal to Savannah Brinson. “It was great that all the friends and family were there to bring in a new year. Even my kids were happy about it, so that’s good. … I feel good. I feel good. It’s a good point in my life right now. My girl, she’s very excited … she’s happy, my family’s happy and that’s what it’s about.”
“Nine years ago today I met this amazing woman in Denver, Colorado. As y’all can imagine, the last half of those nine years hasn’t exactly been smooth,” he said of his engagement to Anna Hansen. “She’s been a pillar of strength and love for me and our entire family. Happy Anniversary, babe. I love you!”
“I wouldn’t say it was love at first sight, I don’t think I’m that type of guy, but I did fall in love later,” the cyclist told Cycling Weekly of meeting his girlfriend, Katarina. “It was three years ago we met. With my dad I wanted to create a sporting centre for young kids. We talked with construction companies about how we could do it. One of the men that I talked to happened to be Kate’s brother. After the Classics, I was in Slovakia for five days and I had a barbecue. I invited her brother, who was passing by my town from some other work. He stopped for the party and she came too.”
“I thought it would be a bit of a laugh but I was a bit embarrassed on it really,” the cyclist said of wooing now-girlfriend Sara Elen on a tandem bike. “I went at the front so I could tell Sara what to do but the pedals weren’t in the right position, which is probably why we ended up on the golf course.”
“We spent two weeks together, that’s how we got to know each other and on the last day before we left, we kissed for the first time in Sydney,” Federer told The Daily Mail about first hooking up with his wife, Mirka.
“Luckily, Amy had a great sense of humor and, fortunately, forgave me for the prank [I pulled on her]. It wasn’t long after the tournament that we started getting really close,” the golfer said of his wife.
“We were talking about it a long time ago,” he told The New Daily of his girlfriend Ajla Tomljanovic. “I sort of pictured it, us playing mixed doubles in front of our home crowd. She told me I was a bit too hard on myself out there. Just being on the court with her, I was in a nice place. It was a little bit tougher at times. It was good though. We practice a lot together. To be honest it was easy. I know what her tendencies are on court, I know what her strengths are so I know what she likes to do out there. It was easy.”
“In my eyes at the time it was a very exclusive place to take her,” the tennis star told The Daily Mail about his first date with now-wife Jelena. “I wanted to impress her so I took her to this place. I knew she liked steak so I ordered for her. I called the waiter over and explained the steak was underdone. He told me I had ordered steak tartare that is always served raw.”
“We haven’t really been putting it out there,” he said of his private courtship of Erica Stoll. “She is from America, which is why I like to spend time in Palm Beach. The past six or seven months have been really nice.”
“I loved playing basketball and we were playing with the ladies there and she was rehabbing,” Watson told Global News of his wife, Angie. “I overheard her talking about golf so I told her I could get us a game. She had no idea who I was – just some goofy guy who played basketball I guess. She saw the staff bag and asked if I was a pro. I told her I’d just turned pro but was still in school.”
Gonzalo Fernández Castaño
“The exact moment I told the media about my idea of getting married I realized she was probably going to find out before I actually got back to Madrid and proposed properly,” the golfer said of his proposal to then-girlfriend, Alicia. “Luckily enough, she said ‘Yes’! That’s probably one of the weirdest marriage proposals ever.”
When Zuckerberg took his now-wife Priscilla Chan out the first time, he told her he’d “rather go on a date with [her] than finish his take-home midterm,” Chan told Today. The line seemed to work.
“I pay attention to what she likes to wear, and you’d be amazed by how often things work,” Bezos, one of the richest men in the world, said of his wife MacKenzie. “Sometimes I call her and say, ‘What’s your such-and-such size?’ and she says, ‘Why?’ and I say, ‘None of your business!’ It delights her….I highly recommend it to any man.”
Morin spelled out, “B, Will you marry me?” for his girlfriend, Brit, on the beach and proposed as the plane flew overhead.
“We met in a general meeting in his office, almost seven years before [we worked together on] Jumping the Broom,” the author and speaker’s now-wife Meagan Good recalled. “I thought he was a guy who gives you a job—he was cute—but that was it. Over the years, we’d see each other at different industry functions, church functions, and then it wasn’t until Jumping the Broom. But even on that movie, it was nine months later before he asked me out!”
“She was the woman who had become my best friend, though for the first six months we were just buddies,” the motivational speaker said to Playboy of meeting his wife. “I was always telling her everything about the women I was dating, and we’d laugh together and have such a great time. She helped me get all those women off the island in Fiji, and I ended up making the choice to be with her. That was the ultimate test.”
“When we first met, she decided to try an Airbnb – and she tried a boat in India and it was a very interesting experience,” the Airbnb founder said of his early dating of artist Elissa Patel.
“Kevin tricked me into thinking that our puppy had run away,” the Instagram cofounder’s girlfriend, Nicole Schuetz, said of his proposal. “So I stormed out of the house in my apron and slippers and he proposed in front of the incredible sunset.”
“I actually started dating Kaitlyn [Trigger] before we started Instagram so it’s been interesting to think about that whole relationship, plus the five years of Instagram,” the Instagram cofounder told USA Today. “I have the dubious honor of launching Instagram, moving apartments and having my one-year anniversary within a week of each other. I have a lot riding on Octobers.”
“I worried I’d become bitter or an old cat guy. But at the end of the day, everybody wants to connect to another human being. When I met Kym, it was just effortless,” the Shark Tank shark told People of meeting DWTS’s Kym Johnson. And if you find yourself on the search for true love, brush up on the 40 Best Dating Tips for Men Over 40.
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