01of 08DO: APPROACH WITH HUMORAndrew H. Walker/REX/ShutterstockNever one to shy away from divulging details about celebrity encounters,Tiffany Haddishrecently dished toThe Hollywood Reporterabout how she propositionedLeonardo DiCaprioa few months back.“I asked him if he’d let me hit that. He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious.’ And then he goes, ‘I mean, I’d do it, but …'“She then revealedshe had a very specific request for theTitanicactor.“I told him, ‘My only stipulation: I wanna do it with you as your character inWhat’s Eating Gilbert Grape,'” the comedian continued. “He starts bustin’ up laughin’, ‘Why?’ he asks, and I say, ‘‘Cause I feel like that performance deserves a real reward and that reward is this [gestures at her own body].'“02of 08DO: GIVE THEM SPACE TO DECIDE WHAT THEY WANT, BUT…Jamie McCarthy/GettyLet them know it’s you.In an interview with Jimmy Fallon onThe Tonight Show,Joe Manganiello opened up about how he knew wife Sofia Vergara was “the one.”He recounted that Vergara had just gotten out of a longterm relationship, and he was flying back and forth to see her while she was filming a project. On his second trip, he noticed thatPEOPLE had featured him on the cover of our “Hottest Bachelors” Issue, and picked up a copy as bait.The two got to talking about their relationship status, and Manganiello said to her, “Look, I know you just got out of this longterm relationship, and if you need to be single, I understand. I’m not gonna like it, but I’ll get over it. But I just need to know if that’s what this is. But before you answer, I want to show you something.” Laughing with Fallon, he explained how he then handed over the copy of the magazine, which Vergara proceeded to flip through. He asked what she was doing when she flipped past his feature, and the actress teased, “I’m seeing who else is on the list!”03of 08DO: SEND OFFBEAT LOVE LETTERSJ. Merritt/WireImageIn an exclusive clip from the actor’s upcoming appearance onMyNext Guest Needs No Introduction with David Letterman, Clooney broke down some of his earliest attempts to win over wife Amal’s heart.Explaining that Amal works as a human rights lawyer, Clooney said he used to write her letters as his dog, Einstein. “I would write letters from Einstein to her saying, ‘I’m being held hostage and I need a lawyer to get me out of the room,'” he told Letterman with a laugh.And it looks like all those silly love letters worked! The pair has been happily married since 2015 and are parents to twins Ella and Alexander.04of 08DON’T: OPEN WITH A JOKEPeter Yang/Comedy Central"It is the most horrible thing,“Daily Showhost Trevor Noah, who’s dating model Jordyn Taylor,told PEOPLE Now. “Jokes require context. Without context, you’re just some random person who came and told someone they fell from [heaven] or some randomness, and if you mess it up you look worse and it seems like an insult. No humor! Just say hello. That’s it!“05of 08DO: FIND A WAY TO GET PHYSICALLY CLOSERSplash News Online"I always used to pull the whole, ‘I’m tired’ thing and put my head on a guy’s shoulder,“Pretty Little Liarsstar Shay Mitchell revealed. “It was so cheesy, but that’s how I got my head on his shoulder! You just have to have fun with it!“06of 08DON’T: BE HUNGOVERFranziska Krug/Getty"I was severely hungover … and I didn’t know Goldie at all outside of having worked with her many years before,“Kurt Russell recalled to Conan O’Brienof striking up conversation with his now-longtime partner, Goldie Hawn. “I just didn’t know in my mind what I was going to see. [Goldie] had a great body, and so the first that came out was ‘Man, you got a great figure.’ And it kind of came out quickly and it could’ve been wrong and she said, ‘Why thank you.'“And while Russell and Hawn’s encounter proved to be successful, considering the pair have been together for over three decades, O’Brien was quick to point out: “You know what’s crazy? You do that and it’s cool, and you’ll end up with her for 34 years. I’ve done that many times in my life and I get maced … it’s a totally different situation.“07of 08DO: GET STRAIGHT TO THE POINTJohn Parra/GettyHey, it worked for John Krasinski!The Officealumnus recounted the first time he met wife Emily Blunt during an appearance onTheEllen DeGeneresShow,telling the host: “I met her and I was so nervous. I was like, ‘Oh god, I think I’m going to fall in love with her.’ As I shook her hand I went, ‘I like you.’ " They tied the knot in 2010 and are parents to daughters Hazel and Violet.08of 08DON’T: PLAY GAMESKevork Djansezian/GettyThose witha penchant for mind games,Chris Prattis talking to you: “The truth is that any amount of trickery or wearing cool shirts with rad designs or using pick-up lines, or any of this bulls— like trying to neg girls, isn’t going to matter. It won’t pay off when she realizes that you’re full of s–t.”
01of 08DO: APPROACH WITH HUMORAndrew H. Walker/REX/ShutterstockNever one to shy away from divulging details about celebrity encounters,Tiffany Haddishrecently dished toThe Hollywood Reporterabout how she propositionedLeonardo DiCaprioa few months back.“I asked him if he’d let me hit that. He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious.’ And then he goes, ‘I mean, I’d do it, but …'“She then revealedshe had a very specific request for theTitanicactor.“I told him, ‘My only stipulation: I wanna do it with you as your character inWhat’s Eating Gilbert Grape,'” the comedian continued. “He starts bustin’ up laughin’, ‘Why?’ he asks, and I say, ‘‘Cause I feel like that performance deserves a real reward and that reward is this [gestures at her own body].'”
01of 08
DO: APPROACH WITH HUMOR
Andrew H. Walker/REX/Shutterstock

Never one to shy away from divulging details about celebrity encounters,Tiffany Haddishrecently dished toThe Hollywood Reporterabout how she propositionedLeonardo DiCaprioa few months back.
“I asked him if he’d let me hit that. He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious.’ And then he goes, ‘I mean, I’d do it, but …'”
She then revealedshe had a very specific request for theTitanicactor.
“I told him, ‘My only stipulation: I wanna do it with you as your character inWhat’s Eating Gilbert Grape,'” the comedian continued. “He starts bustin’ up laughin’, ‘Why?’ he asks, and I say, ‘‘Cause I feel like that performance deserves a real reward and that reward is this [gestures at her own body].'”
02of 08DO: GIVE THEM SPACE TO DECIDE WHAT THEY WANT, BUT…Jamie McCarthy/GettyLet them know it’s you.In an interview with Jimmy Fallon onThe Tonight Show,Joe Manganiello opened up about how he knew wife Sofia Vergara was “the one.”He recounted that Vergara had just gotten out of a longterm relationship, and he was flying back and forth to see her while she was filming a project. On his second trip, he noticed thatPEOPLE had featured him on the cover of our “Hottest Bachelors” Issue, and picked up a copy as bait.The two got to talking about their relationship status, and Manganiello said to her, “Look, I know you just got out of this longterm relationship, and if you need to be single, I understand. I’m not gonna like it, but I’ll get over it. But I just need to know if that’s what this is. But before you answer, I want to show you something.” Laughing with Fallon, he explained how he then handed over the copy of the magazine, which Vergara proceeded to flip through. He asked what she was doing when she flipped past his feature, and the actress teased, “I’m seeing who else is on the list!”
02of 08
DO: GIVE THEM SPACE TO DECIDE WHAT THEY WANT, BUT…
Jamie McCarthy/Getty

Let them know it’s you.In an interview with Jimmy Fallon onThe Tonight Show,Joe Manganiello opened up about how he knew wife Sofia Vergara was “the one.”
He recounted that Vergara had just gotten out of a longterm relationship, and he was flying back and forth to see her while she was filming a project. On his second trip, he noticed thatPEOPLE had featured him on the cover of our “Hottest Bachelors” Issue, and picked up a copy as bait.
The two got to talking about their relationship status, and Manganiello said to her, “Look, I know you just got out of this longterm relationship, and if you need to be single, I understand. I’m not gonna like it, but I’ll get over it. But I just need to know if that’s what this is. But before you answer, I want to show you something.” Laughing with Fallon, he explained how he then handed over the copy of the magazine, which Vergara proceeded to flip through. He asked what she was doing when she flipped past his feature, and the actress teased, “I’m seeing who else is on the list!”
03of 08DO: SEND OFFBEAT LOVE LETTERSJ. Merritt/WireImageIn an exclusive clip from the actor’s upcoming appearance onMyNext Guest Needs No Introduction with David Letterman, Clooney broke down some of his earliest attempts to win over wife Amal’s heart.Explaining that Amal works as a human rights lawyer, Clooney said he used to write her letters as his dog, Einstein. “I would write letters from Einstein to her saying, ‘I’m being held hostage and I need a lawyer to get me out of the room,'” he told Letterman with a laugh.And it looks like all those silly love letters worked! The pair has been happily married since 2015 and are parents to twins Ella and Alexander.
03of 08
DO: SEND OFFBEAT LOVE LETTERS
J. Merritt/WireImage

In an exclusive clip from the actor’s upcoming appearance onMyNext Guest Needs No Introduction with David Letterman, Clooney broke down some of his earliest attempts to win over wife Amal’s heart.
Explaining that Amal works as a human rights lawyer, Clooney said he used to write her letters as his dog, Einstein. “I would write letters from Einstein to her saying, ‘I’m being held hostage and I need a lawyer to get me out of the room,'” he told Letterman with a laugh.
And it looks like all those silly love letters worked! The pair has been happily married since 2015 and are parents to twins Ella and Alexander.
04of 08DON’T: OPEN WITH A JOKEPeter Yang/Comedy Central"It is the most horrible thing,“Daily Showhost Trevor Noah, who’s dating model Jordyn Taylor,told PEOPLE Now. “Jokes require context. Without context, you’re just some random person who came and told someone they fell from [heaven] or some randomness, and if you mess it up you look worse and it seems like an insult. No humor! Just say hello. That’s it!”
04of 08
DON’T: OPEN WITH A JOKE
Peter Yang/Comedy Central

“It is the most horrible thing,“Daily Showhost Trevor Noah, who’s dating model Jordyn Taylor,told PEOPLE Now. “Jokes require context. Without context, you’re just some random person who came and told someone they fell from [heaven] or some randomness, and if you mess it up you look worse and it seems like an insult. No humor! Just say hello. That’s it!”
05of 08DO: FIND A WAY TO GET PHYSICALLY CLOSERSplash News Online"I always used to pull the whole, ‘I’m tired’ thing and put my head on a guy’s shoulder,“Pretty Little Liarsstar Shay Mitchell revealed. “It was so cheesy, but that’s how I got my head on his shoulder! You just have to have fun with it!”
05of 08
DO: FIND A WAY TO GET PHYSICALLY CLOSER
Splash News Online

“I always used to pull the whole, ‘I’m tired’ thing and put my head on a guy’s shoulder,“Pretty Little Liarsstar Shay Mitchell revealed. “It was so cheesy, but that’s how I got my head on his shoulder! You just have to have fun with it!”
06of 08DON’T: BE HUNGOVERFranziska Krug/Getty"I was severely hungover … and I didn’t know Goldie at all outside of having worked with her many years before,“Kurt Russell recalled to Conan O’Brienof striking up conversation with his now-longtime partner, Goldie Hawn. “I just didn’t know in my mind what I was going to see. [Goldie] had a great body, and so the first that came out was ‘Man, you got a great figure.’ And it kind of came out quickly and it could’ve been wrong and she said, ‘Why thank you.'“And while Russell and Hawn’s encounter proved to be successful, considering the pair have been together for over three decades, O’Brien was quick to point out: “You know what’s crazy? You do that and it’s cool, and you’ll end up with her for 34 years. I’ve done that many times in my life and I get maced … it’s a totally different situation.”
06of 08
DON’T: BE HUNGOVER
Franziska Krug/Getty

“I was severely hungover … and I didn’t know Goldie at all outside of having worked with her many years before,“Kurt Russell recalled to Conan O’Brienof striking up conversation with his now-longtime partner, Goldie Hawn. “I just didn’t know in my mind what I was going to see. [Goldie] had a great body, and so the first that came out was ‘Man, you got a great figure.’ And it kind of came out quickly and it could’ve been wrong and she said, ‘Why thank you.'”
And while Russell and Hawn’s encounter proved to be successful, considering the pair have been together for over three decades, O’Brien was quick to point out: “You know what’s crazy? You do that and it’s cool, and you’ll end up with her for 34 years. I’ve done that many times in my life and I get maced … it’s a totally different situation.”
07of 08DO: GET STRAIGHT TO THE POINTJohn Parra/GettyHey, it worked for John Krasinski!The Officealumnus recounted the first time he met wife Emily Blunt during an appearance onTheEllen DeGeneresShow,telling the host: “I met her and I was so nervous. I was like, ‘Oh god, I think I’m going to fall in love with her.’ As I shook her hand I went, ‘I like you.’ " They tied the knot in 2010 and are parents to daughters Hazel and Violet.
07of 08
DO: GET STRAIGHT TO THE POINT
John Parra/Getty

Hey, it worked for John Krasinski!The Officealumnus recounted the first time he met wife Emily Blunt during an appearance onTheEllen DeGeneresShow,telling the host: “I met her and I was so nervous. I was like, ‘Oh god, I think I’m going to fall in love with her.’ As I shook her hand I went, ‘I like you.’ " They tied the knot in 2010 and are parents to daughters Hazel and Violet.
08of 08DON’T: PLAY GAMESKevork Djansezian/GettyThose witha penchant for mind games,Chris Prattis talking to you: “The truth is that any amount of trickery or wearing cool shirts with rad designs or using pick-up lines, or any of this bulls— like trying to neg girls, isn’t going to matter. It won’t pay off when she realizes that you’re full of s–t.”
08of 08
DON’T: PLAY GAMES
Kevork Djansezian/Getty

Those witha penchant for mind games,Chris Prattis talking to you: “The truth is that any amount of trickery or wearing cool shirts with rad designs or using pick-up lines, or any of this bulls— like trying to neg girls, isn’t going to matter. It won’t pay off when she realizes that you’re full of s–t.”
source: people.com