How Much Does It Cost To Be Taylor Swift's Boyfriend?

Joe Jonas was Taylor Swift's boyfriend in what was her first public relationship. The iconic relationship was quite brief, lasting from July to October 2008, which as far as the public knows, didn't give the couple ample time to go on romantic excursions or rent luxury villas together. Given the pair's busy schedules and the relationship duration, Jonas likely took Swift out on a few lunch or dinner dates a month. 

According to a 2009 Rolling Stone article, Swift lived at home with her parents in Hendersonville, Tenessee, a wealthy suburb just outside of Nashville at that time. In 2008, Jonas likely lived in Los Angeles, as he was recording his band's third studio album, A Little Bit Longer, and was involved in several Disney Channel projects including Camp Rock and Jonas. In March of 2008, Jonas was seen leaving an Embraer RJ135 private jet at Luton Airport in London. As of right now, an Embraer RJ135 costs $7,450 per hour and anywhere from $5.7 million to $37.5 million to purchase. 

Expensive dinners in Nashville or Los Angeles back then can cost anywhere from $150 to $500, and while meals can get more expensive in these bustling metro areas, it's safe to assume the Hollywood newbies weren't dishing thousands for Michelin star meals every night.  Due to their busy schedules, if the pair went to dinner twice a month, that would run the bill anywhere from $300 to $1000. So, it's safe to assume Jonas could have spent $1,800 to $6,000 on meals for the pair in total. and if he flew to see her a few times a month via the private jet, the 4-hour flight would be approximately $20,676 a flight back in 2008. If the private jet flew around 3 times a month, the cost would equal around $62,028 a month in travel, meaning the singer likely spent hundreds of thousands of dollars to see Swift.

If Lucas Till looks familiar to you, that's probably because he starred as Swift's love interest in the "You Belong With Me" music video, one of her most iconic songs to date. Till was Swift's boyfriend from March 2009 to April 2009 after meeting on the set of Hannah Montana: The Movie, which was filmed the previous year. Although many details of the relationship have been kept under wraps. Swift was reportedly still living in Nashville with her parents in 2009, which rules out the purchase of any mansions or luxury apartments for the young couple, who at the time, would have been around 20.

Till graduated high school in the spring of 2008, and moved to Los Angeles shortly after, so it's likely that the bulk of the cost of maintaining the short-lived relationship went to dinner dates and air travel costs. Considering that the young couple, who were both in the very early stages of their careers at the time, only dated for a month, L'OFFICIEL estimates that Till spent at most $10,000 during the relationship. 

Throughout the couple's three-month romance in the fall of 2009, Taylor Swift and Taylor Lautner, whom Swifties have dubbed the best ex, were spotted together in public on multiple occasions, ranging from outings to hockey games to exchanging embraces at the 2009 VMAs. By December 2009, the couple broke things off, hence Swift's hit "Back to December," released in her 2010 album Speak Now. “He went everywhere he could to see her, but she didn’t travel much to see him,” said a source close to the former couple to Us Weekly in 2009. “They decided they were better as friends.”

While Lautner was Swift's boyfriend when she lived in Nashville, Lautner traveled to see her at home, at a Chicago date of her Fearless tour, and possibly in met up with her in New York City during Swift's October 2009 SNL appearance. It's estimated that the Twilight actor spent several thousand dollars, at the very least, on airfare, dinner dates in Los Angeles, and tickets to sporting events. 

The pair ended things amicably, but fell out of touch for a while, according to Lautner. Swift, Lautner, and Lautner's current wife—who is curiously also named Taylor—are all close friends. “I’ve always had the deepest respect for who she is as a person before anything else,” Lautner said on the Call Her Daddy podcast in 2023. “So, it’s been really fantastic over the past year. I mean, honestly, I would say one of the greater things to happen in my life over the last year is the rekindling of our friendship because she just is a wonderful human. And she’s pretty great to have in your life.”

Among the most notorious of Taylor Swift's boyfriends, John Mayer dated the pop singer briefly between 2009 and 2010. The relationship has since been criticized due to the age gap between the pair, with Mayer being 32 and Swift just 19 at the time of the romance. Few details have emerged in terms of any potential gifts, exotic vacations, or grand gestures, but given the busy schedules of the two musicians, it's estimated that Mayer likely spent thousands of dollars on travel to see the "Dear John" singer. 

Despite the fact that Jake Gyllenhaal and Swift only dated for a few months, it is estimated that the actor spent hundreds of thousands of dollars on the singer while he was Swift's boyfriend. The most expensive culprit was allegedly a $165,000 private jet flight so Swift could meet up with him in London, as reported by InStyle. 

Gyllenhaal also reportedly rented out a Nashville movie theater for a date with Swift and as a birthday gift, dropped over $10,000 on a Chet Atkins-signed Fender guitar, putting his known total at well over $200,000. 

Conor Kennedy was Taylor Swift's boyfriend during the summer of 2012, and they first sparking dating rumors when the couple was spotted walking hand-in-hand over the Fourth of July weekend in Hyannis Port, Massachusetts. Just a few weeks later, Swift purchased a $4.9 million Cape Cod mansion with the intent of being closer to her then-boyfriend, who was 18 at the time, and his family, who were very supportive of the relationship. Of the singer, Ethel Kennedy, Conor's grandmother, told People in 2012 that “She’s just sensational inside and out.” 

Throughout the couple's short romance, it appears that, unlike previous boyfriends, Conor Kennedy was outmatched by Swift in the spending department, who was bolstered by her hefty Cape Cod real estate investment. It's estimated that the bulk of Kennedy's spending in the relationship can be attributed to date expenses and the occasional flight, putting him at the lower end of the list. 

Swift and Kennedy reportedly amicably split in October 2012, according to Us Weekly, and Swift sold her Cape Cod home shortly after. 

Perhaps the biggest heartthrob couple of the era, Harry Styles was Taylor Swift's boyfriend for several months between late 2012 and early 2013. During the early stages of their relationship, fans spotted Swift wearing a paper plane necklace, nearly identical to Styles' iconic pendant, prompting speculation that the One Direction star bought her a matching necklace.

Aside from jewelry, Styles likely spent a fortune on air travel, as the two were frequently spotted together in New York City during the length of their relationship. Famously, the couple broke up while on vacation together in the British Virgin Islands, and given that the celebrity couple tend to travel in style, a luxury resort and private air travel were certainly among the trip's expenses. All in all, Styles likely spent hundreds of thousands of dollars in maintaining the short-lived, but iconic relationship that inspired several songs off of Swift's 1989. 

Calvin Harris was Taylor Swift's boyfriend in March 2015 after being introduced by singer Ellie Goulding. "Calvin is a really great mate, and he's so fantastic, and Taylor is such a cool person who I love," Goulding said to The Sun via The Mirror. "I thought, 'They're both really awesome and both really tall, they'll be brilliant together."

The couple kept their relationship relatively private, occasionally sharing glimpses of their romance on social media. Harris and Swift attended various events together, including award shows and vacations. They often showed support for each other's work publicly. However, in June 2016, news of their breakup emerged, with reports suggesting that it was amicable. However, following their split, several social media exchanges hinted at tension between the two, particularly regarding songwriting credits for Swift's hit "This Is What You Came For," which Harris produced. Despite this, the pair moved on, with both parties focusing on their respective careers.

Throughout the pair's lengthy relationship, the couple traveled frequently, which is no surprise given the high-profile status of both Harris and Swift. Spotted at countless award shows together, on dates across the country, and on a luxurious tropical getaway in celebration of their one-year anniversary. Given the cost of flying a private jet—which is estimated at $2,000 for one hour in terms of fuel alone—and the delicate gold locket he gifted to the singer engraved with the date of their anniversary, it's safe to assume that the DJ spent millions of dollars during his relationship with Swift. 

Tom Hiddleston was Taylor Swift's boyfriend beginning in June 2016, shortly after Swift's breakup with Calvin Harris. 

The pair were seen at the Met Gala in May 2016, and photos of them kissing on a beach in Rhode Island quickly circulated. However, their relationship faced scrutiny and criticism, with some questioning its authenticity. By September 2016, rumors of their breakup surfaced, and it was confirmed shortly afterward. The romance lasted around three months, and compared to past flings, many details of the relationship were kept under wraps. Minus that iconic t-shirt, of course.

Given the privacy of the relationship, it's estimated that the bulk of the cost, unsurprisingly, went to air travel, as Hiddleston left Los Angeles to spend time with Swift at her Rhode Island mansion. The pair was also spotted in New York, Nashville, England, Australia, and Italy, putting the estimated cost upwards of $80,000, accounting for travel arrangements, dinner dates, and Hiddleston's air travel, although, who knows, it's highly likely that the actor traveled via Swift's famous private jet. 

A drastic departure from the radio silence of the Joe Alwyn era, it seems Travis Kelce and Taylor Swift are making headlines every other day with their whirlwind romance, which has escalated quickly in seriousness since the pair began dating in the fall of 2023. As estimated by The New York Post, Kelce has spent over eight million dollars on Swift since the onset of their relationship. The NFL player spent over a million dollars on a Super Bowl stadium suite so Swift, friends, and family could watch the game, though let's hope he was able to score an insider's discount. He spent millions of dollars jetting across the world to watch Swift's Eras Tour shows, and even bought a new mansion.

In addition to those costs, Kelce's love language is clearly gift-giving, as evidenced by the pricey presents given to the singer. Among the lavish gifts Kelce has given Swift are a $2,199 Valentine's Day floral arrangement, a $3,020 24K gold rose-shaped sculpture, a $1,050 Dior beret, $6,360 matching diamond bracelets, and a $5,100 Bottega Veneta handbag, among others, all of which put Kelce's go big or go home philosophy on full display. Overall, The New York Post calculates that the Super Bowl champion has spent upwards of $8 million on Swift.