It's no secret that Taylor Swift has plenty of celebrity friends, including a high-powered (and high net worth) girl squad. But when the songstress became BFFs with Blake Lively, fans were surprised. The two didn't seem to run in the same circles, but that didn't stop them from becoming close after some Instagram shade initially pushed them together.
Taylor is also said to be close with Blake's husband, and because Ryan Reynolds is also friends with Taylor's ex Jake Gyllenhaal, the waters are muddied in terms of how they're all connected and how Taylor first met Jake.
Taylor Swift And Jake Gyllenhaal Dated For A Season In 2010
In a storyline that Swifties know all too well (literally from her song 'All Too Well,' actually), Taylor and Jake fell in love one autumn, but by winter, they had split. Their large age gap and the seemingly random pairing (they ran in very different social circles, it was clear) might have been partly to blame, but as always, Taylor wrote some breakup ballads and simply moved on.
Swifties didn't let things lie, though, and for years afterward, Jake's sister Maggie Gyllenhaal was repeatedly asked about the red scarf Taylor left behind, and even Jake was nearly speechless after being asked about his personal life one too many times.
By the time they had broken up, Jake didn't want to talk about Taylor at all—but someone else was fine with chatting about setting the two of them up.
How Did Taylor Swift Meet Jake Gyllenhaal?
It wasn't Blake Lively and Ryan Reynolds who connected Taylor Swift and Jake Gyllenhaal, although that would have made for a cute story (and some awkward parties after the split).
In an interesting twist, Gwyneth Paltrow took credit for setting the two up during a dinner party she had hosted. Paltrow was "reluctant" to admit her hand in the setup, but said that Jake was a "great guy" and that they had known one another for a long time.
As for the Taylor connection, Gwyneth explained that her then-husband Chris Martin "has a friendship with Taylor." No word on whether Taylor's budding friendship with Gwyneth survived the conscious uncoupling from Chris, but after the way she and Jake publicly ended, perhaps she steered clear.
Either way, the introduction was a hit, though Paltrow didn't say exactly when that fateful dinner party was. Afterward, around October, Jake began accompanying Taylor out, like to her Saturday Night Live taping that year.
Did Blake And Ryan Set Taylor Up?
By now it's clear that Blake Lively and Ryan Reynolds had no hand in connecting Jake Gyllenhaal and Taylor Swift. But that doesn't mean they're averse to playing matchmaker for their friends.
It turns out that the couple is apparently close with Jake, and in 2018, a "source" told the National Enquirer that Gyllenhaal had asked for a helping hand finding a girlfriend.
The source didn't specify whether Jake had any requirements for his future leading lady, but they confirmed that Ryan was happy to set Jake up on some dates. Given that it sounded as if Jake asked Ryan for help, it's unclear how close Blake might be with the actor.
Fans might assume that since Jake apparently broke Taylor's heart, Blake wouldn't be too eager to help him find someone else, even all those years later. She didn't seem to have any comment on the matter, but also may not have been asked about it.
Other celebrities did have a hand in helping Taylor get over Jake, though. Namely, Anne Hathaway apparently comforted Taylor after the split, which hints at just how far Taylor crossed over into TV and film territory while dating Jake.
Who Did Jake Gyllenhaal Date After Taylor Swift?
Taylor Swift might be the most interesting name in Jake Gyllenhaal's dating history, but she's far from the only celebrity he's stepped out with. Before Taylor, Jake reportedly dated Kirsten Dunst (those two were introduced by Maggie Gyllenhaal), Natalie Portman, and Reese Witherspoon.
After splitting from Taylor, Jake seemed to wait a few months before stepping out with actress Jessica Lowndes. He also saw Minka Kelly for a bit. Then, when 'All Too Well' came out in October 2012, Jake seemed to be dating a mystery brunette who wasn't famous enough to have her name dropped.
Jake then dated a swimsuit model (Alyssa Miller), who publicly admitted to their relationship and "gushed" about the actor (and his cooking skills). Jake's last reported leading lady is a French model named Jeanne Cadieu.
The two were first connected in 2018 when Jeanne was 22 and Jake was 38. For reference, their age gap is larger than Taylor and Jake's—16 versus nine years. While every publication that reports on the relationship seems to call Jeanne "mature for her age," Swifties might have some choice thoughts about that after Taylor's 'All Too Well (10 Minute Version) (Taylor's Version)' music video.
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