Open in App
Showbiz Cheat Sheet

Jake Gyllenhaal Once Dropped $165,000 to Take Taylor Swift on a Special Date

By Jessica Wick,


Even if you don’t follow Taylor Swift at all, you’re probably well aware that she dated Jake Gyllenhaal . The singer and songwriter has penned many a song that are rumored to be about the actor, including the infamous “All Too Well.” But, although their romantic relationship has been over for a decade, there is a tidbit that seems to have remained under the radar: Gyllenhaal once spent a whopping $165,000 to treat Swift to a very special date.

The Jake Gyllenhaal and Taylor Swift timeline
Jake Gyllenhaal poses for photos at the premiere of “Strange World” I Gareth Cattermole/Getty Images for Disney

Swift first met Gyllenhaal at a dinner party hosted by Gwyneth Paltrow and her then-husband, Chris Martin. They were first spotted together in public in October 2010 at a taping of Saturday Night Live, sparking rumors that they were dating. This kicked off a series of paparazzi shots of the couples taking autumn strolls through New York City.

The romance was short-lived — Swift’s reps announced in January that the relationship was over, and Swift made a painful reference to Gyllenhaal not showing up to her 21st birthday party on the Red album. But even though they weren’t together long, their time together clearly made an impact on Swift — she even penned a 10-minute song about him.

The infamous $165,000 date

In November 2010, Gyllenhaal reportedly shelled out an estimated $165,000 so he could take Swift on a very special date. First, he flew her to Luton on a private jet, where he was in town promoting his film, Love and Other Drugs. Swift was scheduled to be in the nearby city of London shortly thereafter to play at the Radio 1 Teen Awards, but she flew in early to spend some quality time with Gyllenhaal.

The couple reportedly stayed in Gyllenhaal’s luxurious suite at The Dorchester. This wasn’t the only time Gyllenhaal spent a fortune to impress Swift — he once bought out all the seats at a movie theater in Nashville so they could watch Tangled together in private.

Why Taylor Swift and Jake Gyllenhaal rumors are resurfacing now


Taylor Swift Fans Could Get Justice as U.S. Senate Announces Hearing Date for Ticketmaster Situation

Obviously, Gyllenhaal and Swift’s romance has been over for quite some time. So why are we still talking about them and their six-figure dates? In 2022, Swift released the “Taylor’s Version” of the Red album, which many have speculated is basically a break-up album between her and Gyllenhaal. Included in the previously unreleased tracks was a brand-new 10-minute version of her hit All Too Well.

While Swift never names names when asked who her songs are about, it’s obvious by the lyrics that the heartbreaking tune details all the highs and lows of their short-lived relationship. So even though the two have long since parted ways, Swift’s fans have been reliving her heartbreak right along with her.

Currently, Swift is dating actor Joe Alwyn, and Gyllenhaal has been with French model Jeanne Cadieu since 2021. But as Swift’s other exes know, dating the pop star typically means that the relationship will live on through her lyrics.

Expand All
Comments / 0
Add a Comment
Most Popular newsMost Popular

Comments / 0