The most expensive celebrity date nights of all time – including Jennifer Lopez's 6-figure getaway

Taylor Swift has now found love with NFL star Travis Kelce, whom she sings about in every other song, but another former flame still lingers in her lyrics. Swiftie sleuths even rumour her new song Pink Clouding is inspired by British actor Tom Hiddleston, and I'm not shocked he has stayed in her mind when you read about this date. 

The pair kicked off their whirlwind three-month romance in 2016 with a lavish date in Rome, Italy. According to E! News, the couple arrived in the Italian city via private jet before enjoying an intimate garden dinner at Hotel de Russie. A night in the penthouse suite (featuring a library, kitchen, 10-seat dining room, marble steam bath, and a 780-square-foot terrace) costs $18,900, wow. After a romantic evening, they apparently enjoyed a private helicopter ride over the city the following day. I would still be writing songs about him too!

The glamorous former couple, who dated for four years from 2017 to 2021, certainly knew how to splurge on date night. After seeing each other for only a couple of months, they flew by private jet to Nice and then on to Paris, racking up a bill of over $180,000 while staying at the ultra-luxurious Le Meurice hotel. If that figure doesn't make your eyes water, the singer also enjoyed a 10-day Caribbean getaway with the former baseball star. They rented a villa at Casa de Campo Resort & Villas in the Dominican Republic, and according to People, the couple paid $10,000 per night for a six-bedroom villa. Of course, that included private balconies, golf carts, a car, breakfast, maid and butler service, a fitness centre, Moët & Chandon champagne, and more. Spending over $60,000 in less than a week shows they were crazy in love.

'Jelena' was the ultimate 2010s teenage dream, and this grand romantic gesture by Justin proved how much he adored her. In 2011, the pair attended fellow Disney star Demi Lovato's concert together before Justin revealed his big surprise. According to TMZ, Justin rented out the Staples Centre in LA (now officially renamed Crypto.com Arena) next door to screen a private viewing of the heart-wrenching film, Titanic. It should be noted that Justin did not actually have to pay for the venue, as the Staples Centre reportedly let him use it free of charge because the pop star had sold out the venue three times. Fitting up to 20,000 people, it was an impressive gesture, and fair play to Justin for landing a bargain.

Going all out, Drake rented out an entire landmark for a date, setting the bar exceptionally high. The rapper reportedly flew content creator Pinkchyu to Toronto and rented out Casa Loma for a private sushi dinner in August 2026. To be clear, Casa Loma is a nearly 200,000-square-foot, 98-room landmark, so it's evident he was pulling out all the stops to impress her. According to TMZ, it was shut down for the evening with only a server, bartender, and security present. If he wanted to, he would, ladies.

Long distance is no obstacle for celebrity couples when one can simply hop on a private jet to visit the other. While dating Travis Scott, the Keeping Up with the Kardashians star made a grand gesture for his birthday by flying across the country to Miami to celebrate. Back in 2021, TMZ reported that they headed for dinner at the swanky restaurant Komodo before partying the night away.

If there is one expensive date idea worth envying, it is catching an international flight to satisfy a food craving. While most of us resist ordering a weekly takeaway, tennis icon Serena Williams and her husband, Alexis Ohanian, caught a last-minute flight to Italy for authentic pasta. The 2018 getaway started as a carb craving and turned into a spontaneous city break in Venice, with the Reddit co-founder posting on Instagram: "She wanted Italian for dinner so..." Photos from the trip showed the couple snuggled up on a gondola, sipping wine and taking in the sights of the ancient city.

For their African honeymoon, Julianne Hough and Brooks Laich outdid everyone. The 2017 holiday started in Seychelles, where they arrived via private helicopter to stay at the exclusive Banyan Hill Estate, where nights cost up to $11,000. They then boarded a private jet to Kenya for a luxury safari at the Angama Mara resort. The Dancing with the Stars favourite likely spent around $21,000 to hang out among the wildlife, but if there is ever a time to splurge, it is your honeymoon!