Dating in Hollywood is fickle, with so many options its hard for some to commit. There are so many beautiful people that its hard to pick just one, and it becomes really hard for the biggest serial daters in Hollywood. That’s why for some celebs their dating history looks like a carousel of guys. It always starts off with great intentions and then bam, its over and it's off to the next hot hookup. They jump from relationship to relationship. And when it’s over there is usually some drama attached. But sometimes you need to kiss a few frogs to find the ‘one.’ And these serial daters have no problem leaving their exes in the dust if the next one appears to be a better match.
And then there are the women who are always apparently single. Sure they may have dated in the past, but they aren’t always on the arm of a significant other. Some may be secretly dating, while others thrive on being single. They have no issues walking the carpet alone or having a lunch with just friends. These celebs are not spotted at hotspots with the newest, hottest celebs, they have low-profiles on the dating scene and want to keep it that way.
20 Serial Dating Queen: Taylor Swift
Taylor Swift is as known for her relationships as she’s known for her songs. We’ve all seen grow as an artist and add to her dating resume at the same time. She often writes songs about her past loves something that some of her exes dread. But it makes for great music and a ton of great quotes on love.
"In fairy tales, the bad guy is very easy to spot. The bad guy is always wearing a black cape so you always know who he is. Then you grow up and you realize that Prince Charming is not as easy to find as you thought..."
"...You realize the bad guy is not wearing a black cape and he's not easy to spot; he's really funny, and he makes you laugh, and he has perfect hair." Taylor has written a ton of hits based on her former relationships like "Style" and "Out of the Woods," which are reportedly about her short courtship with Harry Styles. Taylor Swift has been linked to Tom Hiddleston, Calvin Harris, Harry Styles, John Mayer, Joe Jonas and Jake Gyllenhaal among a few others. Taylor is currently dating actor Joe Alwyn and they have been together for about a year.
19 Single With Kids: Charlize Theron
Charlize is a proud single mom. But she always seems to be single.“Once you have children, that’s who you are. There’s no way around that. That’s who I am. Once I had my kids, the first two years you’re so -- you turn into such a mom. Your body almost switches off. I had no desire to date or anything.” She does still date though she said according to Parents, "I went on a date maybe, like, a month ago. I had a great date, I’ve got to tell you. I had an incredible date. This guy really impressed me. I think he was just like a really cool dude. I think some people try to be cool, I think he was just cool. ... We went for a 9 mile hike in the middle of the night. It was a full moon. I was really impressed. It was fun! I’m not going to say where we met, but we met somewhere, and we ended up going for a walk. I wasn’t scared -- it was just really fun. He was super funny. It was super private and I guess that’s what made it so much fun too.”
Charlize dated Stuart Townsend for almost a decade before splitting in 2010 and then she dated Sean Penn for a year and a half before they split up in 2015. Since then she has remained under the radar on the dating scene.
18 The Back-Up Dating Plan: Jennifer Lopez
Jennifer Lopez is no stranger to dating, she’s been married three times and has been involved in a few high profile relationships in addition to her marriages. But Jennifer believes in love and has the dating history to prove it. And a set of high standards she said according to Marie Claire,
“I have my own high standards for what I want in a partner and how I want to be treated. I bring a lot to the table. I’m not talking about material things but what I have to offer as a person – love and loyalty and all the things that make a good relationship.”
But she’s a little known for her dating history, like when she ended her relationship with Ben Affleck and landed with Marc Anthony right away. Maria Shriver once asked Jennifer, "Right away when you broke up with Ben Affleck, Marc Anthony was there like 2 days later, and you were in." "Right, you're absolutely right,” Jennifer said according to Today.com “It was probably my first big heartbreak, and to have one of my best friends who I'd known for years who I actually love and did have chemistry with come into my life and say, 'I'm here.' What you need to know is, nobody can save you or heal you. Only you can do that for you," said according to Today.com
Jennifer was married to Marc Anthony and has dated Diddy, Ben Affleck, and Casper Smart and had been linked to Drake.
17 Single Throne: Emilia Clarke
Emilia Clarke must fly real low on the dating radar since her last real public boyfriend may have been Seth MacFarlane and that was years ago and only for a short time, but it was hard dating another celebrity she said according to Us Magazine.
"Well, a con is you have strangers giving you love-life advice. Like, ‘I’m a big fan of the show [GoT], and I’m not sure what you’re doing with that guy,’ which I didn’t react well to..."
"...That happened in New York when Seth and I were together. This guy started to give me advice: ‘Can I get a selfie? And by the way … ' Unh-unh, bro." She says she’s dated other people since that relationship. "It's funny. I've dated other people, but he was the only one that the Internet found out about. But I kind of set myself with a little rule this year: NMA. No More Actors. And yet it's almost the only bloody choice; they're practically the only people I know!" But the Game of Thrones actress does want to have a family, but not necessary marry. "Yes, I want babies. I don't know about marriage. That's probably quite a painfully millennial thing to say. But I do want to find a human that you'd want to create a family with," she told Elle. So its hard to tell if Emilia is in a relationship or not?
16 Dangerous Dater: Ariana Grande
Its all very new but Ariana Grande recently called it quits with rapper boyfriend Mac Miller in the past few weeks and this week it was announced that she was already dating a new guy, SNL’s Pete Davidson. Ariana had to defend herself after she was blamed for Miller’s recent DUI. She wrote, “how absurd that you minimize female self-respect and self-worth by saying someone should stay in a toxic relationship because he wrote an album about them, which btw isn’t the case (just Cinderella is ab me). I am not a babysitter or a mother and no woman should feel that they need to be. I have cared for him and tried to support his sobriety & prayed for his balance for years (and always will of course) but shaming / blaming women for a man’s inability to keep his [explicit] together is a very major problem. Let’s please stop doing that. of course, I didn’t share about how hard or scary it was while it was happening but it was. I will continue to pray from the bottom of my heart that he figures it all out and that any other woman in this position does as well,” she said according to People.
This isn’t the first time that Ariana has addressed her dating life. After she split from Big Sean she became upset at her relationships making headlines. "I’m tired of needing to be linked to a guy. I’m not Big Sean’s ex, I’m not Niall’s new possible girl. I’m Ariana Grande," said in a Tweet via Teen Vogue. In the long message, Ariana wrote, "The double standard and misogyny are still ever present. I can’t wait to live in a world where people are not valued by who they’re dating [or] married to [or] attached to [or] having [explicit] with...but by their values as an individual. I want the people reading this to know that they are more than enough on their own."
Ariana has dated Big Sean, Mac Miller and Jai Brooks and dancer Ricky Alvarez.
15 The Perks Of Being Single: Nina Dobrev
Nina Dobrev might be dating actor Glen Powell, or she might not, but she always seems single. Her last high profile romance was with Ian Somerhalder since then she has been linked to her best friend Julianne Hough’s brother, Derek and then to Glen. Nothing seems to last long.
"You either have chemistry or you don't, but a lot of what attracts me is a guy's mind and humor and talent," Nina said of relationships with the LATimes. "I need to get to know all those things before I fall for someone. I'm not a one-night-[only] kind of girl. I'm a relationship girl."
She continued, "I'm progressive in some ways, old-fashioned in others. I like it when guys hold the door open and are sweet and thoughtful. The guys on our show are really good at that. A man in a suit looking put together and dapper is very attractive, but I also kind of like the I-just-rolled-out-of-bed, a-little-bit-of-scruff, effortless, not-trying-hard-but-still-sexy guy. If a guy spends more time looking in the mirror than I do, that's a problem!"
Nina and Glen may be taking some time apart. "There hasn't been an official 'split' but Nina and Glen have been taking time apart," an insider told E! "Nina just wrapped on a project and is about to start another and her schedule has been a huge part of it. They haven't been spending much time together since the end of the summer."
14 Reality Star Dater: Khloe Kardashian
Khloe Kardashian just like her sister Kim has had no shortage of suitors, although things just don’t always work out even when she puts her relationships first. “I do like to put my relationships as a priority, and I really try to make that work. As long as people are making the effort to do so, I think anything can work,” Khloe once said according to People.
Khloe has had trouble with relationships especially with Lamar Odom who’s infidelities and substance issues contributed to the demise of their relationship. When Khloe attempted to rebound with rapper French Montana, things just didn’t work out. “I don’t know if I believe in rebounds unless you just sleep with someone for a night or two. They’re just people you can laugh and have a good time with. My life is so serious, or always moving so fast, it’s fun to have that outlet to enjoy and let your hair down and not worry about things.” By now Khloe knows that relationships are hard.
“The most confused you will ever get is when you try to convince your heart and spirit of something your mind knows is a lie,” she reportedly said about love according to People.
Khloe is currently dating Tristan Thompson, was married to Lamar Odom, and dated French Montana and James Harden among a few other possible hookups.
13 Single Top Model: Tyra Banks
Tyra Banks was in a long-term relationship with the photographer, Erik Asla. They even welcomed a son together, but the duo called it quits after 5 years. But you would never know that Tyra is even in a relationship as she keeps mum on most of her relationships.
Tyra was so heartbroken after split years with boyfriend, John Utendahl at the time, that she went on a spiritual retreat with friends. "Tyra has gone away with a female friend and has been island-hopping, visiting Bali And taking a spiritual retreat," according to Page Six. These days Tyra is all about her son and her work, she hosts America’s Got Talent. "I'm tired right now because I was up all night. He was waking up all night last night, and [needed a] bottle at 5:30 this morning. I do have a lot of help, but I don't have help all the time. So those moments when I'm like, in it and suffering, I'm like, 'This is what I'm supposed to be doing as a mama'" she told ET. Tyra has not mentioned dating since she split in 2017 from Erik and don’t count on a relationship announcement. That’s not Tyra’s style.
12 Serial Dark Horse Dater: Katy Perry
Katy Perry’s now in a serious relationship with Orlando Bloom, they split up for a little while but have found a way back to each other. “I fall in love every time. And I don't really fall in love a lot, but when I do, I fall hard,” she said about love according to Hello.
But relationships haven't been very smooth for the pop star turned American Idol judge. Remember when she married Russell Brand.
“At first when I met him he wanted an equal, and I think a lot of times strong men do want an equal, but then they get that equal and they’re like, I can’t handle the equalness. He didn’t like the atmosphere of me being the boss on tour. So that was really hurtful, and it was very controlling, which was upsetting. I felt a lot of responsibility for it ending, but then I found out the real truth, which I can’t necessarily disclose because I keep it locked in my safe for a rainy day. I let go and I was like: This isn’t because of me; this is beyond me. So I have moved on from that,” Katy told Vogue. That was always an odd match, right? And he broke it off via text.
Katy has dated Travis McCoy, Russell Brand, John Mayer, and is currently with Orlando Bloom.
11 Single in Wakanda: Lupita Nyong'o
Who is Lupita Nyong’o dating, no one knows! And Lupita might never tell you. When she was asked about her relationship status at the moment she said, "You can ask, but you definitely won't get an answer. There have been rumors and rumors and rumors about my love life. That's the one area that I really like to hold close to my heart," according to PopSugar.
Lupita has seemingly learned from other celebs to keep her relationships private. But she was very flirty with her ‘Black Panther’ co-star Michael B. Jordan, who gushed over the actress during her March birthday. “She looks elegant right?! Graceful! Timeless! No this is the look of a killer getting ready to give me push-ups in knee-deep popcorn !!!” he wrote on Instagram according to People. “I’ve had the pleasure of knowing what a beautiful soul you have & witness you shine your light on the world through your work your passion your joy & in everything you do. Those of us who are lucky enough to know you personally are definitely changed for the better! HAPPY BIRTHDAY!!!”
They were rumored to be very flirty while promoting the movie, but she’ll never tell the truth about her relationship.
10 Rules Don’t Apply For Serial Dater: Lily Collins
Lily Collins is a low radar serial dater. She’s not an in your face kind of actress, so her relationships will stay low-profile, but that doesn’t mean she isn’t dating around. “Love will find you again, And you can never, ever change yourself for anyone or change yourself to fix the relationship. So if it isn't healthy, say good-bye,” Lily wrote in her book, Unfiltered: No Shame, No Regrets, Just Me according to Goodreads.
Lily may have played a princess on screen but she knows that’s not how life works necessarily, especially with her dating history.
"My advice for girls who are waiting for their Prince Charming is to be open for anything. Be open to new experiences, be open to the idea that it may take longer than you want, but if you're open to meeting new people and new adventures, then love will come along," she told Seventeen. But she says she needs someone who will love her in her pajamas. “I’ve learned a lot about myself because of the relationships that haven’t worked out. I’ve had some good and some bad relationships. I want someone to make me laugh. I need to just be enough for someone. I would like to be accepted in my pajamas or wearing something glamorous,” Lily said according to The Mirror.
Lily has been linked to Nick Jonas, Taylor Lautner, Zac Efron and Jamie Campbell Bower, who she may be currently dating.
9 Always Single on Valentines Day: Jennifer Garner
Jennifer Garner didn’t plan to be a single mom of three when she married Ben Affleck over a decade ago. But after their 2015 split Jennifer found herself single and not ready to mingle at all. "I would not have chosen this life for myself or for my kids," Garner told news.com.au according to GoodHousekeeping. "I would not choose to be single or be in this position. It's something that we are working through."And Jennifer has not moved on as quickly as Ben has. "I haven't been on a date and I am not interested in dating. People want to set me up and I am just like, 'No thank you!'"
But lately she’s been thinking about her future, but her children will always come first. "She wants to be very careful and very selective when she does find the time to date—because of the kids," an insider told ET. "She hasn't made dating a priority. Jen wants to make sure that when she finally does decide she is ready for romance that her next man is in it for the long run. Men are last on Jen's list. First comes her children, then her career and then a man."
Ben has since moved on to girlfriend, Lindsay Shookus.
8 Dating Life Sentence: Lucy Hale
Lucy Hale has been dating in Hollywood for a few years now so she’s encountered a few mean guys. "I've definitely hung out with people where I've been in a social setting and they were rude to the waiter or rude to someone, which is my biggest pet peeve. I’ve had instances where someone drank too much and I saw their true colors. Nothing too catastrophic has happened, though.” But she continues to date nonetheless.
“I’ve sort of jumped from relationship to relationship and I’m just now at the point in my life where I’m allowing myself to date people without getting attached," she told Teen Vogue. "I’m a late bloomer."
Lucy Hale has been linked to Anthony Kalabretta, Adam Pitts, Chris Zylka (who is engaged to Paris Hilton) and is dating Riley Smith her Life Sentence co-star with who she was spotted on Valentine’s Day outing with. “Lucy Hale left Pace restaurant holding hands after a romantic Valentine’s meal. The actress was also grasping onto her pink rose as they waited for around 10 mins for vale to bring their car,” an witness told Us Magazine, “She leant over to kiss and hug him a few times during this period and was also seen sucking his lollipop that the restaurant gives to their customers for after meal.” She might be off the dating market.
7 Keeping Up With Single Kendall Jenner
Kendall Jenner is not like her sisters, she does not flaunt her relationships for the public. She tried to keep them as quiet as possible, but its hard when you might be dating one of the most recognizable basketball players on the court, Blake Griffin and you grew up on a reality show. "I'm not marrying anyone. I'm not engaged. There's nothing long-term or serious like that in my life. If I'm not fully, fully in it with someone, why would I make it public to everyone else? If I don't even know what it is, why would I let the world know?" She told Harper's Bazaar, "I think it's something sacred. It's something between two people, and nobody else's opinion needs to be involved in it. People want to start drama. If I had a boyfriend, people are going to say all this stuff that's probably going to cause us to break up. I'm doing my thing.I'm having fun. I'm being young. BUt Kendall always tetters on being single and they may have already split especially since Blake has been traded to Detroit Kendall was last linked to ASAP Rocky! But Kendall could be dating anyone right now she’s so discreet.
6 Serial Dating Angel: Cameron Diaz
Cameron Diaz used to be linked to the hottest men in Hollywood, Alex Rodriguez, Jared Leto, Justin Timberlake and Matt Dillon. But now that she’s 100% committed to her husband, Benji Madden,"You know what? Nothing matters now that I have my husband," Cameron told Andy Cohen on his SiriusXM show according to Today.
"I don't even remember any of that. Like, that's the thing. That's how I know he's my husband because there's … no one compares. Everything else just washes and slips away."
She continued to gush over married life. "You realize, 'Oh, right, this is what the real thing is. This is what real love is. This is what real commitment and devotion is. This is the person you build your life with … and I know that this is special." Cameron can’t imagine her life without Benji now. "Yeah, it’s one of those things where everybody tells you, 'You just know when you know,' and I was always like, 'What does that mean?'"She said and then she met Benji. "And I was like, "Oh, I get it! You just know when you know. You’re my husband.'” Cameron is definitely over dating in Hollywood, but one of her bestie’s Drew Barrymore is back on the market now that her marriage is over.
5 Always Seemingly Single: Mindy Kaling
The only person that Mindy Kaling has ever been romantically linked to was her Office co-star B.J. Novak. “I will freely admit: My relationship with B.J. Novak is weird as hell. He is not my boyfriend, but he is not my best friend.” Mindy told Instyle according to People. “I guess you could describe our relationship as a ‘romantically charged camaraderie with loud arguments,’ but I don’t think Facebook would accept this as a new status,” she added.
Mindy recently welcomed a daughter she named Katherine, but there was no mention of a daddy. Currently, she is a single mommy and learning to deal with mommy guilt after returning to work. “I've had to learn to release myself from mom guilt at least a couple times a day,” she told InStyle. “That's been a big one for me. I’m also learning to feel better about asking for help, whether it's from family or hiring help. It’s not profound, but I love my career and I don't want to make myself feel bad about pursuing both. Just cutting myself some slack has been very helpful for me.”
Mindy will soon be promoting Ocean’s 8 with Sandra Bullock and Rihanna.
4 The Don Jon Serial Dater: Scarlett Johansson
Sorry, Colin Jost, Scarlett Johansson doesn’t quite believe in monogamy, hence her dating history. “Scarlett likes to be in control,” an actor once told Page Six about Scarlett’s relationships. “Then, when she gets it, she gets bored.” And boy they didn’t lie.
But Scarlett isn’t too fond of marriage after marrying Ryan Reynolds and Romain Dauriac, “I think the idea of marriage is very romantic; it’s a beautiful idea, and the practice of it can be a very beautiful thing.” But the actress then diverted her thoughts a little,
“I don’t think it’s natural to be a monogamous person. I might be skewered for that, but I think it’s work. It’s a lot of work. [It] is such work for so many people – for everyone – the fact of that proves that it is not a natural thing..."
"...It’s something I have a lot of respect for and have participated in, but I think it definitely goes against some instinct to look beyond.”
Scarlett is currently dating SNL’s Colin Jost, but she was married to Ryan Reynolds and she dated, Sean Penn, Josh Hartnett, and Jared Leto. Colin alluded to their relationship during a Weekend Update when he confirmed he had a girlfriend.
3 Always Kind Of Single: Rihanna
Rihanna’s always kind of single until now, she’s rumored to be dating businessman, Hassan Jameel and yet she still seems single. And she has talked about her lonely life as an international pop star. “It is lonely, but I have so much work to do that I get distracted. I don’t have time to be lonely. And I get fearful of relationships because I feel guilty about wanting someone to be completely faithful and loyal, when I can’t even give them 10 percent of the attention that they need. It’s just the reality of my time, my life, my schedule,” Rihanna told Vanity Fair.
But things have changed since she’s turned 30. “I used to feel guilty about taking personal time,” she told Vogue, “but I also think I never met someone who was worth it before.” She continued, “Even mentally, just to be away from my phone, to be in the moment, that has been key for my growth. Now, when I come to work, I’m all in. Because before you know it, the years will go by. I’m glad I’m taking the time. I’m happy.”
Rihanna has dated Chris Brown, Drake and Matt Kemp. And she’s been linked to Travis Scott and Leonardo DiCaprio.
2 Serially Dating Around: Kate Hudson
Kate Hudson’s definitely a serial dater. After her split from Matt Bellamy, she reportedly took a two-year break after her brother told her to take some time off.
“He’s the one that when Matt and I broke up was like, ‘Don’t get into another [explicit] relationship.’ I was like, ‘I won’t!’ and he’s like, ‘Please, I give it four months.’..."
"...And the other day, I realized it’s been almost two years!” Kate was linked to Nick Jonas around 2016, but the relationship never materialized into anything serious. She added that she followed her brother’s request. “I did a full-on ‘I’m not even gonna text with anybody, I’m not gonna flirt’ — I’m gonna shut it all down. I’ve got great kids and friends. I’m not shutting out men, but for the first year after Matt, I did … especially [because] I’m such a flirt! I love to flirt.” She is currently dating Danny Fujikawa and expecting a baby girl together. Kate has only been married to Chris Robinson, but she dated Matt Bellamy (and they share a son) and Owen Wilson, and Alex Rodriguez. And she was linked to Derek Hough and Lance Armstrong. Kate has finally settled with Danny.
1 Always Single And Ready To Mingle: Chelsea Handler
Chelsea Handler has been single for some time now and she says she can’t find a date and doesn't care. “I can’t get anyone to date me. You know and I’m not that really interested, to be quite honest. A little [explicit] here and there is not even that interesting to me anymore. I need to be really interested, there are too many things going on in the world that I want to be focused on. You would have to be really fantastic to get me to lose my focus.” Despite her reluctance to dating she is on dating app she said according to ET Online. “I’m trying to see if, like, do I still even like [explicit] I mean, I don’t think about it a lot. So, I was worried maybe I forgot about it.”
While talking with Ellen Chelsea said she wouldn’t find love. “I haven't met anyone really great. Maybe I never will, maybe I’m just not cut out for it. I don’t think love is the answer, do you?” Ellen answered, “Oh, I do think love is the answer.” But Chelsea is cool being single, “It is important for women to have a positive outlook about being single. It is empowering to know who you are and know that I won’t settle for anything less than what I bring to the table.”
References:E!, Parents, Marie Claire, Today, Us Magazine, Elle ,People, Teen Vogue, LA Times, E!, People, Page Six, ET,Hello, Vogue, PopSugar, People, Good Reads, Seventeen, The Mirror, GoodHousekeeping, ET, Teen Vogue, Us Magazine, Harper’s Bazaar, Today.com, People, Instyle , Page Six, Page Six,Vanity Fair, Vogue, Page Six, ETOnline
