15 Flirtiest Celebrity Guys Of All Time

in Cringeworthy
15 Flirtiest Celebrity Guys Of All Time

Flirting has always been an art form because not everyone can pull it off. Yes, flirting as part of one’s character in a movie or TV show is doable if one is a good actor. But flirting in real life can be tricky because not everyone has the innate ability to reel in their target. Women these days are not the demure damsels of yesteryear, because women of the past could easily be fooled to fall for the next flirt’s pick-up lines. But fortunately, the modern female is very astute and she can tell when a man is trying to get into her pants or just being plain friendly.

Flirting has many forms. Friendly flirting is harmless because usually, it’s just the guy’s way of making conversation, which can maybe lead to going for a drink or dinner. Sexy flirting, on the other hand, complete with smirks and lascivious winks, can mean he wants to get you into bed. The important thing is to know the difference and decide if you want to take him up on his flirtatious ways or not. Here are some of the biggest flirts in Hollywood.

15. Leonardo DiCaprio


He may only be in his 40s, but Leonardo DiCaprio has had a stellar career that has spanned more than two decades. He had his breakout roles when he was in his teens in the films This Boy’s Life and What’s Eating Gilbert Grape, for which he was nominated for an Academy Award. He has played numerous ground-breaking roles throughout his career, but until this year, he was fast becoming that actor who was always nominated for Oscars, but was never fortunate enough to take home the best acting plum. He finally lucked out when he won for Best Actor for the film The Revenant at the 2016 Academy Awards show. Aside from finally having that much-coveted gold statue, DiCaprio is also considered to be a ladies’ man to the beautiful women of the catwalk. It seems like his last string of relationships has been with gorgeous supermodels: Kristen Zang, Emma Miller, Gisele Bundchen, Bar Refaeli, and he is currently seeing hot, young thing Nina Agdal.

14. Ian Somerhalder


Is it any wonder that Ian Somerhalder is considered a big flirt? With his piercing gray eyes, chiseled mouth, and amazing cheekbones, he doesn’t even have to shoot you a smoldering look to make your panties drop to the floor. But he certainly knows how to work that smolder, especially to his female fans. He first hit the TV scene when he played Boone Carlyle in the TV drama Lost, but it was his role as Damon Salvatore in the supernatural drama The Vampire Diaries that catapulted him to immense popularity. It didn’t help that he began dating his co-star Nina Dobrev, with whom he had an insane amount of chemistry. These days, he has happily settled down with actress Nikki Reed, but he’s still got that flirty side to him. He has pleased the legions of girls in his fan base, especially in China, where he participated in some flirty games in a variety show, charming the pants off the ladies.

13. Joe Jonas


It wasn’t until recently that Joe Jonas broke out of the mold and started carving a niche for himself on his own because let’s face it, he was always just known as “that Jonas brother.” Jonas Brothers. For those who weren’t big fans of the trio singing group of brothers, he was a relative unknown—just one of the three siblings. But he has since ventured out on his own and released his own solo album in 2011, called Fastlife. He decided to form a new band called DNCE, which released its first album in 2015 with the single “Cake By The Ocean” which was a huge hit, enabling the band to gain a good following. One claim to fame of this Jonas boy was the string of famous women he has dated: Taylor Swift, Demi Lovato, Ashley Greene, and Gigi Hadid. Does that spell ladies’ man or does that spell ladies’ man? Of girls, he has said, “When I’m with a girl I like, I usually give her hugs and little nudges, and flirt without her knowing it!”

12. Wilmer Valderrama


Some actors play a part that’s very different from their actual personalities in real life, which is the absolute beauty of acting: you can change characters after a good amount of internalization and be someone completely different each time. In Wilmer Valderrama’s case, he didn’t seem too far off the mark when he played shameless flirt and ladies’ man Fez in the sitcom That ‘70s Show. Though he has ventured into film and even launched a music career, he is still most known for his role as Fez. That, and the fact that he’s a huge flirt. He has a way with words and can really turn on the charm, by showering women with compliments and hugs. He’s also quite famous for his personal life, having dated a string of beauties, such as Mandy Moore, Mischa Barton, Lindsay Lohan, Minka Kelly, and most recently, Demi Lovato.

11. Ne-Yo


Ne-Yo is just the famous R&B singer’s stage name and he probably changed it to have his own brand of uniqueness in an otherwise saturated music industry, although his real name (Shaffer Chimere Smith) is quite unusual too. He gained fame in 2004, when his song “Let Me Love You” topped the music charts. He has a bunch of other hit songs under his belt, like “Sexy Love,” “Because of You”, and “Closer.” He’s had his share of legal troubles, for reckless driving and driving without a license. This father of three is a bonafide flirt and finds a girl’s mouth quite sexy. He was once quoted as saying, “Anything drawing attention to your mouth always leads to a kiss! Put on lip gloss, eat finger foods, or drink from a straw. There’s no cool way to drink from a straw, but there is a flirtatious way—you know what I’m talking about!”

10. Usher


Not many celebrities outright say that they are flirts, let alone womanizers, but Usher has not been one to mince words when it comes to having a harem of women. He is a jack of all trades, having gained success for his talent in singing, song writing, dancing, and even acting. His hit songs include “You Make Me Wanna…”, “Nice and Slow,” “U Got it Bad,” “Yeah,” and “Burn” and he has been touted as one of the best selling music artists. He is widely regarded as a sex symbol and this manifests in the way he moves onstage and the way that he expresses his lyrics. He’s also known to be a good kisser and his womanizing persona was further solidified when he revealed that he wanted the Playboy kind of life after a failed marriage. He has referenced Hugh Hefner, saying he’d like to find women who are open-minded, women who wouldn’t mind being amongst other women with him at the center of the lot, similar to Hefner’s Playboy mansion. He eventually changed his womanizing ways and settled down with his second wife in 2015.

9. Simon Cowell


He’s most known as a reality TV judge with an acerbic tongue, never sugar coating his words when he gives his critique of contestants. Simon Cowell may give off the impression that he’s a “right git” as the British love to say, but he’s actually a very astute judge of character with a good business sense and charming personality to go with it. He’s worth over $300 million, thanks to his entrepreneurial skills and for a time, he made it to Time magazine’s list of 100 most influential people in the world. He’s also a philanthropist, involved in a good number of charities and is even a patron of the UK charity Together for Short Lives. He was engaged for a time and was said to have dated Carmen Electra, but it was his involvement with married woman Lauren Silverman that threw him into controversy because it was found out that she was pregnant with his child. Fortunately, things were settled out of court and he went on to become a proud daddy to a little boy.

8. Sebastian Stan

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Perhaps the earliest role most girls associate Sebastian Stan with is that of Carter Baizen, that spoiled brat of a boy who hated Chuck Bass and seduced Serena van Der Woodsen in the teen drama series Gossip Girl. He also had small roles in other projects like TV shows Kings, Once Upon a Time, Political Animals, and the 2010 film Black Swan. But the role that Stan is perhaps most known for is Bucky Barnes in the Marvel hit film Captain America: The First Avenger. He has reprised his role several times over in the Marvel universe film franchise and along with his status as a heartthrob, he’s surely enjoying the fruits of his fame. He’s had his share of women, having dated Gossip Girl co-star Leighton Meester, Glee’s Dianna Agron, his Once Upon a Time co-star Jennifer Morrison, and currently, his Spread co-star Margarita Levieva. He’s not shy about his status as eligible bachelor, playfully flirting with Sharon Stone, who was his teenage crush, on The Late Late Show with James Corden.

7. John Mayer


He broke into the music scene in the early part of the 2000s and at that time, John Mayer’s niche was acoustic rock. But he made the wise move to veer towards the blues and started collaborating with big names of the blues genre. He is the singer behind such hit songs as “Your Body Is A Wonderland,” “No Such Thing,” and “Why Georgia.” He has gained attention from the media for his personal life almost as much as his music. Notoriously known as a womanizer, he has dated several beautiful celebrities on a consecutive basis, including Jennifer Love Hewitt, Jessica Simpson, Minka Kelly, Jennifer Aniston, and Katy Perry. He was said to have had an affair as well with Taylor Swift, an incident which supposedly caused a rift between Perry and Swift, who used to be good friends. Fighting over a known womanizer is indeed the stuff that tabloids are made of.

6. Harry Styles


As boy bands go, One Direction is probably one of the most popular ones and they’ve often been compared to their fellow Brit band, The Beatles. The band decided to go on hiatus in March 2016 and this has given an opportunity to its members to pursue solo careers. Perhaps the most popular member of the band is Harry Styles, who signed a recording contract as a solo artist and has really branched out on his own, writing songs and collaborating with other artists like Ariana Grande and Michael Buble. He was in a brief relationship with Taylor Swift, whose hit song “Style” is supposedly about him. Apparently, he was a flirt even as a child, according to his elementary school soccer coach. Styles has a way with words, according to his teacher, “always sweet-talking somebody.” He has carried this flirty nature with him into his adulthood and he’s known as the king of flirting with girls on stage.

5. Justin Bieber


You either love him or hate him. There doesn’t seem to be an in-between with Justin Bieber. Back when he was just starting out in the music business, the Canadian singer and songwriter became an instant hit with his pre-teen fan base, when he released his hit song, “Baby,” which is his most successful single to date. When his audience grew up and outgrew him, he changed up his music style so that it had a more upbeat, mature sound to it. But unfortunately, he has landed in tabloids not just for his music, but also for his personal life, which includes legal troubles, such as reckless driving, driving under the influence, and vandalism. He’s had high-profile relationships with Selena Gomez and Sofia Richie, but being in relationships hasn’t stopped him from being a flirt to his female fans. He is known to have posed for photos, where he touches or looks at fans in a manner that borders inappropriateness. He even called his best friend Hailey Baldwin “hot” when he still had Instagram.

4. Chace Crawford

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He was quoted by Seventeen magazine saying, “I like messing with girls…just a game back and forth so the girl doesn’t have to feel like she has to be ultra-polite…It’s a roundabout way of flirting.” Chace Crawford is proud of the fact that he’s quite creative when it comes to flirting and coupled with his good looks, he can certainly pull it off with much élan. He’s most known for playing scion Nate Archibald in the teen drama TV series Gossip Girl, though his role in the show as a Vanderbilt scion is quite far removed from his real life upbringing. Born and raised in a middle-class home in Texas, he made his film debut in the 2006 horror flick The Covenant. After Gossip Girl, he tried his luck again on TV in the short-lived drama series Blood and Oil. Though his popularity is nowhere near his co-star Blake Lively’s, he’ll always be that heartthrob that knows how to flirt.

3. George Clooney


No one ever thought that George Clooney would ever settle down, after one failed marriage had made him declare that he didn’t think he wanted to get married again. He first gained public recognition when he played Dr. Doug Ross in the medical drama ER and this paved the way for roles in mainstream films like Batman and Robin, Three Kings, and the Ocean’s Eleven film installment. He has had a string of successful films since then, in the capacity of actor, producer, and director. Clooney won an Academy Award for Best Supporting Actor in the film Syriana. As a producer, he won Best Picture for the Ben Affleck-directed film Argo. Out of the many awards show he has attended in his illustrious career, he always seemed to have a different woman on his arm. His list of conquests includes Renee Zellweger, Krista Allen, Elisabetta Canalis, and Stacy Kiebler. But it was British-Lebanese human rights lawyer Amal Alamuddin that eventually got him to tie the knot, hopefully this time, for keeps.

2. Colton Haynes


With his chiseled features and baby blue eyes, Colton Haynes has turned many a head throughout the years. The American actor and model is best known for his role as Jackson Whittemore in the MTV supernatural drama series Teen Wolf. He later left the show to play superhero, which is a dream for many actors. He took on the character of Roy Harper, also known as the superhero Arsenal in the superhero TV series of Arrow, which belongs in the DC universe. His character was written out of the show, but he has other projects lined up for him. He publicly came out as gay in May 2016, but that hasn’t stopped the charmer from hamming it up with girls. He was known to have gotten all flirty with Lucy Hale on Twitter and he has tons of Instagram posts where he gets all affectionate with girls, including his Arrow co-star, Emily Bett Rickards.

1. Jake Gyllenhaal


He comes from a prominent acting family and with a director for a father, a screenwriter for a mother, and an actress for an older sister, was it any wonder that Jake Gyllenhaal would get into the acting business himself? But he doesn’t just ride on the coattails of his family’s accomplishments. He has made a name for himself, thanks to his acting choices and the roles that he has decided to take on. It doesn’t help that he’s oh-so easy on the eyes. He received rave reviews for his performance in Ang Lee’s Brokeback Mountain, for which he starred opposite the late Heath Ledger. His personal life has had its fair share of media glare as well. He was in long-term relationships with Kirsten Dunst and Reese Witherspoon and had brief romance with Taylor Swift. He has been known to be a playful flirt, which is not surprising, given the females constantly ogling him.

Sources: seventeen.com, j-14.com, msn.com, popcrunch.com

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