Allow These 14 Iconic Celebrity Dates to Inspire You This Valentine’s Day

Love is in the air. 

In February, it's natural to feel it, but if you look for it—romance is around all the time. In fact, there are plenty of celebrities who celebrate their relationships in small—or extravagant—ways 365 days a year. 

Indeed, some celebrity relationships are the ideal blueprint for romance. From young love like Zac Efron and Vanessa Hudgens' five-year relationship in the late aughts (that included a lot of frozen yogurt outings) to the big reputation of Travis Kelce and Taylor Swift's whirlwind stadium-attracting affair, celebrity couples manage to create some super sweet dates for themselves. 

And while fans may feel they know Taylor's time in the bleachers private suites all too well, more than a few stars have managed to pull off sweeping romantic gestures away from private eyes. (We're looking at you Rihanna and A$AP Rocky.) 

Everybody loves a solid celebrity couple's red carpet moment—still waiting on Travis and Taylor's—but there's something extra special about seeing, or hearing about, a really great celebrity date night. After all, these A-listers have the world at their fingertips, so they might as well use the opportunity to make the world—and their partners—swoon. 

If you're pressed for a quick Valentine's Day plan for you and your partner, one of these iconic duos may just inspire you. As for those flying solo at the moment, these dates are sure to set your expectations sky high the next time you swipe right. 

Read on for the 14 of the best celebrity dates of all time. 

While this celeb couple is firmly a thing of the past—with Justin Bieber nearing his sixth wedding anniversary with wife Hailey Bieber, and Selena Gomez happily committed to boyfriend Benny Blanco—fans of the iconic duo swooned when news broke that the “Baby” singer had rented out the entire Staples Center (now Crypto.com arena) for dinner and a movie back in 2011.

The extravagant moment was reportedly inspired by a scene in Adam Sandler’s Mr. Deeds, TMZ reported at the time, in which Adam’s character wows Winona Ryder’s Babe Bennett by similarly renting out Madison Square Garden for a date.

After leaving a Demi Lovato concert at Nokia Theater on Sept. 23, Justin, then 17, reportedly led a 19-year-old Selena to the arena, surprising her with a candlelit meal and a screening of Titanic. 

Any Taylor Swift fan can probably remember where they were when it was first reported that the “Karma” singer had been spotted in a suite at Arrowhead Stadium on Sept. 24, 2023, cheering on Travis Kelce as the Kansas City Chiefs took on the Chicago Bears last September. 

And while the entire evening was a lavender craze of excitement and a football game makes a worthy first (public) date, fans were particularly kicking their feet at Travis whisking Taylor off to an after party in a 1970 Chevelle 408 Stroker convertible, per People, or rather, the couple’s first getaway car. 

Starting with their on-screen meet cute in the Spider-Man franchise, Tom Holland and Zendaya have earned their reputation as one of Hollywood’s most adorable pairs with outings to a Beyoncé concert, Los Angeles Lakers games, and, of course, tons of red carpets—but one of their sweetest moments is a bit more lowkey. 

In Aug. 2023, Tom and Zendaya participated in a local volunteering event in Oakland, Calif. put on by Hoopbus, Project Blackboard and Oaklandish for a day of cleaning up West Oakland Middle School’s playground and some basketball (although the Euphoria star herself didn’t play). 

And since the Challengers actress has been known to give back to her community regularly—including visiting Fruitvale Elementary School where her mother Claire Stoermer once taught—the day date proves just how much the couple have integrated interests in their almost three years together. 

Just as rumors emerged that Bennifer was indeed back, the Gigli stars added fuel to the rekindling flames with a romantic trip to Italy in July 2021. In addition to a stroll around the city, the pair were seen engaging in some hardcore PDA while aboard a yacht. 

This romantic trip—timed to J.Lo’s 52nd birthday—all but confirmed the duo were totally in love again. As for how Jennifer felt rebounding so quickly after her broken engagement with former MLB star Alex Rodriguez? “She’s totally in love with Ben and only has eyes for him,” a source told E! News at the time. “She has moved on and is not looking back.” And time has proven it so. 

The friends to lovers arc between A$AP Rocky and Rihanna was finally completed during summer 2020. Amid the pandemic, the couple—who now share children RZA, 21 months, and Riot, 6 months—took a cross country road trip that definitely caused them to have love on the brain. 

“I love the simple things but also the grand adventures,” she told Vogue in 2022. “There’s no pretentious my-brand-your-brand bullshit, it’s just us living—I just feel like I can do any part of life by his side.” 

A$AP reportedly picked up and tie-dyed gas station T-shirts, while Rihanna took care of their meals. “I cooked our food on this little janky grill I bought from Walmart,” she added. “I still have it, too. It works like nobody’s business.” 

It may as well be a couple’s rite of passage to survive a trip to Disney together. Duos spotted at the parks include Ariana Grande and Ethan Slater, Rebel Wilson and Ramona Arguma, Travis Barker and Kourtney Kardashian. 

Kristin Stewart and fianceé Dylan Meyer passed this milestone back in Jan. 2022, along with pals such as Ashley Benson (who has also made a romantic excursion out of the theme park with ex Cara Delevingne), CJ Romero and Suzie Riemer. The squad deemed themselves a “family,” and even snagged some matching sweatshirts to prove it. 

A surprisingly private pair, Timothée Chalamet and Kylie Jenner have only had a handful of public moments since confirming their relationship. As for how they made things official though? Their most iconic date thus far was a very public display of affection at Beyoncé’s birthday concert in Los Angeles Sept. 4, 2023—which was also attended by Kylie’s sisters Kim Kardashian and Khloe Kardashian, as well as her mom Kris Jenner.

The duo were spotted in videos enjoying the show—and each other— in the VIP section of SoFi Stadium. 

“That was great,” the Dune star said of the iconic evening in a Dec. 18 MTV interview. “Hard to be present.” 

All the single ladies can learn a thing or two about the art of the rebound from Emily Ratajkowski—and Harry Styles. On the heels of breakups from long term partners—Emily officially divorced Sebastian Bear-McClard in September 2022 and Harry split with girlfriend of two years Olivia Wilde in November of the same year—this duo was spotted Mar. 2023 having a heated smooch session on a street in Tokyo. 

The pair’s liplock was one that temporarily rocked the internet, but—despite the “As It Was” singer admitting years earlier that the model was his celebrity crush—nothing serious ever came from this golden moment. As the Grammy winner himself once said, if you like having a secret little rendezvous, then he’s perfect for you. 

They’ve now been happily hard launched for about two years—and engaged since November 2023, but when Channing Tatum and Zoe Kravitz were spotted on a romantic bike ride in New York City back in August 2021, their relationship status was still up in the air. 

So the pair really got speculation rolling when Zoe hopped onto the pegs of Channing’s bicycle for a ride around the East Village. The High Fidelity alum was photographed with her arms around the Magic Mike star’s neck, and less than a month later, they confirmed their relationship to the press. 

The first day Nick Jonas met Priyanka Chopra at the 2017 Vanity Fair Oscars party , the “Sucker” singer reportedly got down on his knees and asked, “Where have you been all my life?” 

And by their third date, which took place a year later in 2018, they’d already reached a turning point in their relationship. After a Memorial Day weekend trip that included drinks at Chateau Marmont, a live performance of Beauty and the Beast, and a Los Angeles Dodgers game, Nick was certain he’d never get hit with a lovebug like Priyanka again. 

In fact, he called his mom shortly afterward, and told her he was going to marry the Indian actress, recounting to Vogue in a 2018 interview: “She walks into the Chateau, and I feel an overwhelming sense of peace and understanding about this next chapter of my life.”

Rustin star Colman Domingo described his first date with his husband of 10 years, Raúl Domingo, as a “Barbara Walters-style” session of questions and answers at a bar in San Francisco. And while the date itself is fairly standard, the Euphoria actor already knew he’d found the love of his life by the time he’d walked in. 

The star first stumbled upon his husband in a Walgreens parking lot in 2005, but other than locking eyes, the pair didn’t interact. A few days later, the Color Purple actor was perusing Craigslist for a used iPod touch, and happened to click over to the Missed Connections page—where people share the information about someone they spotted and wanted to get to know better. There, he read a missive from his future spouse: “I saw you outside of Walgreens in Berkeley.” 

While sharing the story to GQ in 2021, Colman added: “I literally jumped out of my chair when I saw the post.”

On a 2024 episode of The Graham Norton Show, Colman recounted the details of their first date again, adding that the pair spent the night together. “We cuddled. I thought he was asleep—4:00 in the morning,” he recalled. “I couldn't sleep and I said, 'I think I love you and you're about to change my life.' And we've been together for almost 19 years.”

This High School Musical couple was much more lowkey during the height of their relationship than fans may recall. In fact, while they walked several red carpets together, the pair’s favorite pastimes were going to the gym and grabbing Pinkberry frozen yogurt in Los Angeles, according to a 2007 People profile. 

However, the iconic Disney duo did channel their inner romantic spark during a 2008 trip to Hawaii. The week after High School Musical: Senior Year hit the big screen, Zac and Vanessa attended the wedding of Zac’s manager, Jason Barrett, on Oct. 25—and took some solo time during a romantic beach date the next day. 

The couple—who officially cut ties in 2010—were photographed displaying some major PDA during their Sunday beach stroll. And though this romance is a thing of the past—Vanessa wed baseball player love of three years Cole Tucker in 2023—this date, and couple, was one to remember. 

Before LeBron James played his first NBA game, he found his forever teammate in now-wife Savannah James. The pair—who now share children LeBron “Bronny,” Jr., 19, Bryce, 16, and Zhuri, 9—met around 2002 when they were 16 and 17 years old, and attending rival high schools. At first, Savannah—who knew nothing of LeBron’s basketball skills at the time—wasn’t into the athlete, but eventually gave him a shot, telling Cleveland Magazine in 2018, “He seemed interested, so let’s see.’”

Their first date was technically among a group, as LeBron invited Savannah to one of his high school basketball games. Afterward, they went to Applebee’s with friends. Their second date? Outback Steakhouse. And that’s all Savannah needed to know her future husband was end game. 

“I knew he loved me when I left my leftovers from dinner in his car. I'd totally forgotten about them, and he brought them to me,” she told Harper’s Bazaar in 2010. “I think he just wanted another excuse to come and see me.”

Before they were one of the most beloved celebrity couples, Ryan Reynolds and Blake Lively were no more than Green Lantern costars. However, the Deadpool actor was able to recall the date that changed everything: A late night bite turned dance session in New York City. 

“We were hanging out at this little restaurant in Tribeca that's open really late, and this song came on and I was just like, "Want to dance?" No one was in there, so it was just totally empty,” he explained in a 2016 GQ profile. “And it was just one of those moments where halfway through the dance, it was like, ‘Oh, I think I just crossed a line.’ And then I walked her home. And, uh, you know, I don't really need to go into what happened after that.”

And Ryan—who now shares four children with Blake including daughters James, 9, Inez, 7, Betty, 4, and their 2023 arrival—remembers the exact song, too. However, he wouldn’t say, adding: “You're shut out.”