12 Celebrity Engagements We Predict Will Happen in 2019

STYLECASTER | Celeb Engagement Predictions
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What’s in store for Hollywood romances in the new year? Our celebrity engagements 2019 predictions include both long-time and short-time couples. From a former Bachelorette contestant who fell in love with a sitcom actress to two Grammy winners who started their romance as mentors on a reality TV show, these Hollywood love stories sure are interesting. Though not every celebrity couple on this list has been dating for a long time (some of these romances started in 2018), there’s no doubt their chemistry is undeniable, and it’s about time to seal the deal with a ring.

2018 didn’t disappoint when it came to whirlwind celebrity engagements and weddings. (Remember when Priyanka Chopra and Nick Jonas married only months after their engagement? And who could forget Miley Cyrus and Liam Hemsworth’s secret wedding after almost a decade of on-again, off-again dating?) We’re hoping 2019 will follow suit with some fan-favorite celebrity couples putting a ring on it and tying the knot.

So far, this year has already kicked off with some expected engagements. (We’ve been calling Chris Pratt and Katherine Schwarzenegger for a few months now.) But will these predicted couples get engaged in the near future? Only time will tell, but we’re putting our money on “yes.”

Wells Adams and Sarah Hyland

In a very 21st-century way, Adams and Hyland’s romance started in August 2017 when the Modern Family actress tweeted about the Bachelorette alum as the bartender on Bachelor in Paradise. “OH MY GOD @WellsAdams IS THE FRIKKIN BARTENDER?! Best. Season. Ever,” she tweeted, to which Adams responded, “Taking applications for #BIP5 bar backs now. Please send references..Preferably from Phil Dunphy. I’m kidding the job is yours @Sarah_Hyland.” The two went public with their relationship in October 2017 when they celebrated Halloween together as a couple and went as two Stranger Things characters. Since then, the two have been inseparable. They moved in together in August 2018 and celebrated their one-year anniversary in October 2018. But is an engagement in the cards?

In January 2019, Adams told Us Weekly that an engagement is “definitely going to happen.” “Everyone thinks [Sarah and I are] engaged right now. We are not engaged, let me just say that,” he said. “We just moved in together, so I think we’re still kind of, like, feeling each other out, but… it’s gonna happen eventually.” A couple weeks later, Adams responded to haters who think Hyland pays for everything in their relationship, including her own engagement ring. “Can I go on the record right here? I will pay for this ring, I promise you. It will come out of my bank account, okay?” Adams on his podcast, Your Favorite Things, adding that his “pet peeve” is when fans assume “Sarah pays for everything.”

STYLECASTER | Celeb Engagement 2019 Predictions | Wells Adam and Sarah Hyland

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Taylor Swift and Joe Alwyn

According to Swifties, Swift and Alwyn’s love story began in May 2016 when they attended the Met Gala while Swift was still with her now-ex-boyfriend, Tom Hiddleston. They started dating soon after and have been in a serious relationship for almost two years. And though the two have been private about their romance, they’ve become more public about their relationship over time. In December, Swift showed her love for Alwyn’s movie, The Favourite, on her Instagram. In January, she attended the 2019 Golden Globes in support of her British beau. Engagement rumors around the couple have circled for some time, especially given reports that they’ve moved into a home together in London.

In December, a source told Us Weekly that the couple will be engaged “soon.” What’s stopping them? Alwyn’s idea for an “unforgettable” proposal. “Joe is very keen on proposing soon,” the source said. “But he wants to make it unforgettable and extremely special. He’s her dream guy. Taylor’s going to be over the moon.”

STYLECASTER | Celeb Engagement 2019 Predictions | Taylor Swift and Joe Alwyn

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Colin Jost and Scarlett Johansson

Sometime after Johansson hosted Saturday Night Live in March 2017, she went on a date with Jost, who writes and stars on the show. Their romance heated up when she attended an SNL after-party in May 2017 and was seen on a date with Jost in July 2017. After meeting each other’s families, Jost and Johansson went public with their relationship in November 2017 at the American Museum of Natural History Gala. Since then, the couple have been as close as ever. And though there have been engagement rumors (such as in March 2018 when Johansson was seen with a diamond ring on her wedding finger), neither Jost nor Johansson has confirmed the talk. Guess we have to wait for a proposal in 2019. (Crossing our fingers.) “I’m very happy. I feel very lucky. She’s pretty cool … it’s hard to have a lot of complaints, she’s pretty awesome,” Jost told People of Johansson in September 2018.

STYLECASTER | Celeb Engagement 2019 Predictions | Scarlett Johansson and Colin Jost

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Shayna Taylor and Ryan Seacrest

Taylor and Seacrest may not make as many headlines as some of the other couples on this list, but they’ve been together for a couple years and we expect a proposal any day now. Seacrest and Taylor’s relationship first dated from March 2013 to December 2014. After they broke up, the couple went their separate ways for three years before reuniting in 2017. Though Seacrest has never been engaged, he does see it in his future. Could it be with Taylor? “I’ve never been engaged, I do believe I would. I did get close, and I didn’t do it and it was the right move, but I love the idea of marriage because my parents have been married for 47 years,” he said on a 2017 episode of Live! With Kelly and Ryan. “The truth is, I don’t want to screw it up. And a lot of times, [marriages] get screwed up, so I figured the longer I wait, the older I’ll be, the closer to death I am, so I can get it in and not screw it up.”

STYLECASTER | Celeb Engagement 2019 Predictions | Ryan Seacrest and Shayna Taylor

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Orlando Bloom and Katy Perry

Bloom and Perry have been dating on and off since January 2016 when they first met (and flirted) at a party. They went public with their relationship in May 2016 and dated for 10 months before breaking up in March 2017. They rekindled their romance in February 2018 and have been going strong ever since. In October 2018, a source told Us Weekly that an engagement is “definitely a possibility” after the couple “worked out all their kinks” that led to their first breakup. “Getting engaged is definitely a possibility in the future,” the source said. “Katy and Orlando have worked out all their kinks and have had really fluid communication about what each of them wants. Katy doesn’t want this relationship to be a repeat cycle of things she’s already experienced in past relationships that didn’t work out. She’s learned to grow from them and doesn’t want that in her current relationship.”

STYLECASTER | Celeb Engagement 2019 Predictions | Katy Perry and Orlando Bloom

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Travis Scott and Kylie Jenner

Scott and Jenner’s relationship has moved fast since they started dating in April 2017, after they were seen flirting at Coachella. In February 2018, the couple welcomed their first child together, a baby daughter named Stormi Webster, and they’ve been haunted by engagement rumors ever since. The rumors, which happen any time Jenner is seen with a ring (or instagrams herself with a proposal-like setting, like a room full of red roses), reached an all-time high at the 2019 Super Bowl, where fans expected Scott to get down on one knee during his halftime show performance. The proposal didn’t happen, but that didn’t stop fans from speculating that Jenner was still engaged because of the ring she wore afterward.

As for if a proposal is on Scott’s mind, it is. In a December 2018 interview with Rolling Stone, Scott talked about the engagement rumors and how he’s keen on proposing, as soon as he thinks of a “fire” way to do so. “We was just two kids, fucking around. Maybe, like, the first week, you don’t know if it’s real or a fling. Then the second week you’re like, ‘Whoa, I’m still talking to her, she’s responding, I’m responding. We ain’t run out of a thing to say.’ And it got to a point where I was like, ‘I need her with me to operate. She’s that one,'” he said.“We’ll get married soon. I just gotta sturdy up—I gotta propose in a fire way.”

STYLECASTER | Celeb Engagement 2019 Predictions | Kylie Jenner and Travis Scott

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Tristan Thompson and Khloé Kardashian

Thompson and Kardashian have been dating for almost three years. They were first seen together in August 2016 and by September 2016, they made their relationship official. In April 2018, days after Thompson was caught cheating on Kardashian at a club in Washington D.C., the couple welcomed their first child, a baby daughter named True Thompson. Despite Thompson’s infidelity, Kardashian has remained faithful to their relationship. On the topic of engagements, there have been rumors, after Kardashian was seen with a diamond ring, but sources claim that there has been “no mention of an engagement yet.”

“Khloé and Tristan are really focused on doing what’s best for [daughter] True,” a source told Us Weekly in January 2019. “They are not going to get engaged anytime soon. The focus right now is on whatever is best for True. Tristan is trying everything he can to regain her trust, but Khloé is spending more time in L.A. because True has so many family members and such a support system there.” Could this be a ploy to keep Kardashian in the dark for a surprise proposal? Who knows.

STYLECASTER | Celeb Engagement 2019 Predictions | Khloe Kardashian and Tristan Thompson

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Katie Holmes and Jamie Foxx

Holmes and Foxx had been dating for secret for almost seven years before they confirmed their relationship at a Grammys party in January 2018. And though they’ve remained private, the couple is slowly opening up to the public eye. In October 2018, photos came out of Holmes wearing a ring on her left ring finger as she filmed her movie, The Secret. The actress’s representatives shut down the rumors, claiming that the ring was simply a prop. But that doesn’t mean that an engagement isn’t in the cards. The couple have been together for more than eight years. But even if they were to get engaged, considering how private they are, we would maybe not even know about it.

STYLECASTER | Celeb Engagement 2019 Predictions | Katie Holmes and Jamie Foxx

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Jennifer Lopez and Alex Rodriguez

Lopez first met Rodriguez in May 2005 when she was still with her ex-husband, Marc Anthony. But it wasn’t until late 2016, when Lopez ran into Rodriguez at a restaurant that they started something romantic. Hours after their run-in, Anthony asked Lopez out. At dinner, when he excused himself to the bathroom, he sent her a text, writing, “You look sexy AF,” according to Vanity Fair. The rest is history. The two have met and introduced each other to each other’s families (both Rodriguez and Lopez have kids around the same age), and they seem to be happy. Of course, there are also engagement rumors.

In December 2018, Lopez told USA Today that she’s not engaged, but she understands why people want her to be. “Everyone wants a fairy tale. They all want a romantic comedy, a happy ending. We all do,” Lopez said. “But it’s not a movie, even if you see us on Instagram or on the shows,” Lopez said. “We’re happy. We’re taking it day-by-day. And it’s great. 2018 has really moved us to place where we feel like a real family. That’s nice. And it’s good enough right now.” When pressured by Ellen DeGeneres to reveal whether or not she and Rodriguez were planning to get married, Lopez told the host, “I don’t know. I don’t know!”

STYLECASTER | Celeb Engagement 2019 Predictions | Jennifer Lopez and Alex Rodriguez

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Britney Spears and Sam Asghari

Spears and Asghari first met in 2016 when she was cast as a model in her music video for “Slumber Party.” “I think we were shooting and we were doing this scene where I was doing the walk scene through the hall to go through the door to go to the bedroom, and we were sitting there and we were waiting and waiting together for 20 minutes at a time,” Spears told AMP 103.7. “So we were basically forced to talk to each other and he has no idea—I mean, he knows my name—but he doesn’t know me as a person. He’s like ‘What is this girl like?’ and I have no idea who the hell he is.”

The two ended up bonding over sushi, with Asghari giving Spears his number. After that, it took Spears five months to finally call him and they’ve been inseparable ever since. (One look at their workouts together on Instagram and you know that they’re a match made in fitness heaven.) As for an engagement, a source told Us Weekly in July 2018 that wedding bells are very likely “Sam will be with Britney for [her] entire tour and they are more in love than ever,” the source said. “Even though Sam is younger than Britney, he is extremely nature for his age. Don’t be surprised if they get engaged in the next year.”.

STYLECASTER | Celeb Engagement 2019 Predictions | Britney Spears and Sam Asghari

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Blake Shelton and Gwen Stefani

An unlikely couple, Shelton and Stefani first met on season 12 of The Voice in April 2014, where they both served as mentors. But it wasn’t until November 2015, after they both divorced their spouses at the time, that a romance heated up between the two singers. “Gwen and Blake are longtime friends who have very recently started dating,” a representative said. Naturally, engagement rumors have followed the couple. When DeGeneres confronted Stefani with the rumors in December 2018, she shot them down. “We’re not. We’re not engaged, and we’re not married. And he’s my boyfriend still,” she said. However, a source for Us Weekly, says otherwise. “[Stefani and Shelton] are going to be announcing their engagement very soon,” the source said in January 2019.

STYLECASTER | Celeb Engagement 2019 Predictions | Blake Shelton and Gwen Stefani

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Bella Hadid and The Weeknd

Hadid and Weeknd first dated from May 2015 to November 2016. After that, they were rumored to date other stars; Hadid with Drake and Weeknd with Selena Gomez. They reunited in November 2017 and have been going strong ever since. In October 2018, it was reported that the model and the singer signed a lease together for a penthouse in New York City. As for an engagement, a source told Us Weekly in November that a proposal is very likely. “They’re madly in love with each other,” the source said. “A proposal is on the horizon.”

STYLECASTER | Celeb Engagement 2019 Predictions | Bella Hadid and The Weeknd

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