Left: Taylor Swift at the Grammy Awards in February. Right: President Donald Trump in the Oval Office in August. Credit - Frazer Harrison (L), Anna Moneymaker (R) — Getty Images Everyone seems to be talking about America's perhaps most famous couple, singer-songwriter superstarTaylor Swiftand three-time Super Bowl-winning football player andpodcasthostTravis Kelce, getting married. Even the President. Not too long ago, Donald Trump said he "hates" Swift, whoendorsedhis Democratic opponent Kamala Harris in last year's presidential election after he hadfalsely implied that she endorsed him. Since then Trump has called Swift a "woke singer" who is "no longer hot." But that didn't stop him from offering his well-wishes after Swift and Kelceannounced their engagementon Tuesday. "I wish them a lot of luck," Trumptold reportersduring a Cabinet meeting at the White House just hours after the news. "I think he's a great player, I think he's a great guy, and I think that she's a terrific person, so I wish them a lot of luck." In his many years as a public figure, Trump has been known tooffer his thoughtson news aboutcelebritiesand theirrelationships. Here's a rundown of the times Trump has commented on Swift. As Swift received the Best Female Video award at the MTV Video Music Awards for "You Belong With Me" on Sept. 13, rapper Kanye Westnotoriously interruptedher speech, saying, "Beyoncé had one of the best videos of all time." Many celebritiesspoke outin defense of Swift. Speaking toTMZ, Trump reacted to the "disgusting" outburst, calling for a boycott of the rapper "so this kind of thing doesn't happen again." Trump claimed West "couldn't care less about Beyoncé" and was merely "grandstanding to get attention." TrumpcalledSwift "fantastic" in a 2012 post on Twitter and thanked her for a "beautiful picture." It's unclear what the context of the post was or whether a photo was taken of the two together, though they both appeared the following month in astar-studded Macy's commercial. "Re: Taylor and Conor--great news for Taylor!" Trumpposteda few months later on Twitter. The post came after Swift'sreported breakupwith Conor Kennedy, son of Robert F. Kennedy Jr., Trump's future Health Secretary. "Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5," Trumppostedon Twitter a few days later. "Taylor is terrific!" In an interview with Yahoo! Politics, when asked what he thought of Swift, Trumpsaid, "terrific." While he hadn't publicly commented on the singer for years, he had appeared to remain a fan: the previous December, Trump's wife Melaniaposted on Facebooka video clip of Trump driving his car while Swift's music was playing on the stereo. Swift grabbed headlines after her firstforay into politicsbyendorsingTennessee Democrats Phil Bredesen, who was running against incumbent Republican Marsha Blackburn, for the U.S. Senate and Jim Cooper for the House of Representatives. Trump, who was midway into his first term as President,reactedto reporters outside the White House: "You know, Marsha Blackburn is doing a very good job in Tennessee, she's leading now substantially, which she should. She's a tremendous woman. I'm sure Taylor Swift doesn't know anything about her. And let's say that I like Taylor's music about 25% less now, OK?" In an interview with conservative news outlet The Daily Caller, Trumpreactedto reports of thebudding romancebetween Swift and Kelce. "I wish the best for both of them. I hope they enjoy their life, maybe together, maybe not—most likely not." At a rally in Houston, Trump mentioned Swift when discussing the "Justice For All"recordingof the Star-Spangled Banner by a group of defendants jailed for their alleged involvement in theJan. 6, 2021, Capitol riot. "When that came out, it went to the number one song," Trumpsaid. "It was beating everybody. It beat Taylor Swift, it beat Miley Cyrus, who was number one and two. They were number one and two. We knocked them off for a long time." ("Justice For All" debuted atopBillboard's Digital Song Sales Chartin March 2023 and also reachedNo. 1 on iTunes.) At the start of the election year, Trump accused Swift of being "disloyal" to him if she were to endorse Joe Biden. Swift had not yet announced her endorsement, though she had supported Biden in 2020 and hadoccasionally publicly criticized Trumpin the years since. "I signed and was responsible for the Music Modernization Act for Taylor Swift and all other Musical Artists," Trumppostedon Truth Social. "Joe Biden didn't do anything for Taylor, and never will. There's no way she could endorse Crooked Joe Biden, the worst and most corrupt President in the History of our Country, and be disloyal to the man who made her so much money. Besides that, I like her boyfriend, Travis, even though he may be a Liberal, and probably can't stand me!" According to a newly-publishedexcerptof a book byVarietyco-editor-in-chief Ramin Setoodeh, Trump described Swift as "unusually beautiful." "I think she's beautiful—very beautiful!" Trump reportedly told Setoodeh during 2023 interviews for the book. "I find her very beautiful. I think she's liberal. She probably doesn't like Trump. I hear she's very talented… I think she's very beautiful, actually—unusually beautiful!" Trump also questioned Swift's political leanings: "She is liberal, or is that just an act? … It surprises me that a country star can be successful being liberal." As the election drew nearer, Trumpshareda handful of AI-generated images that suggested Swift backed his presidential bid and wanted her supporters to too. "I accept!" hepostedalongside the images. After Swiftmade clearthat she endorsed the Democratic ticket, TrumptoldFox & Friends, "Well, I actually like Mrs. Mahomes much better, if you want to know the truth," referring to Brittany Mahomes, the wife of Travis Kelce's Kansas City Chiefs teammatePatrick Mahomes. "She's a big Trump fan." Trump declared that he was "not a Taylor Swift fan," noting that her Harris endorsement was disappointing but not surprising. "She's a very liberal person. She seems to always endorse a Democrat, and she'll probably pay a price for it in the marketplace," he said. Days later, on Truth Social, Trumpposted: "I HATE TAYLOR SWIFT!" Earlier this year, Swiftattended the Super Bowlto support Kelce, who was competing for a third consecutive and fourth career NFL championship. Trump was also in attendance and, while he was also backing the Chiefs, who ultimately lost, he appeared to glory in the fact that some Philadelphia Eagles fans booed Swift when she was shown on the jumbotron at the stadium in New Orleans. Trumpshared a videoof the booing on Truth Social, and he separatelyposted: "The only one that had a tougher night than the Kansas City Chiefs was Taylor Swift. She got BOOED out of the Stadium. MAGA is very unforgiving!" While hosting the victorious Eagles at the White House in April, TrumpmentionedSwift again. "It was an incredible game. A little surprising, but right from the beginning of the first quarter of the big game," he said, before appearing to depart from his script, "which I was there, I watched in person. I was there along with Taylor Swift. How did that work out? How did that one work out?" He then went back to recapping the game: "The Eagles scored a touchdown on their signature play…" Without any clear prompt, Trumppostedon Truth Social in May: "Has anyone noticed that, since I said 'I HATE TAYLOR SWIFT,' she's no longer 'HOT?'" About the comment, a White House officialtold CBS News: "As a business and entertainment mogul President Trump is highly qualified to comment on the rise and fall of various celebrities." Aftercontroversy ignited over an American Eagle adfeaturing actorSydney Sweeney, whose "great jeans"—a seeming wordplay on great genes—sparked social media backlash over alleged racism, Trumpweighed inwith a Truth Social post. The President praised Sweeney, "a registered Republican," and said American Eagle had "the 'HOTTEST' ad out there." He went on to lambast other companies for going "woke," which he claimed was bad for business, before offering Swift as an example. "Just look at Woke singer Taylor Swift," he said. "Ever since I alerted the world as to what she was by saying on TRUTH that I can't stand her (HATE!). She was booed out of the Super Bowl and became, NO LONGER HOT. The tide has seriously turned — Being WOKE is for losers, being Republican is what you want to be. Thank you for your attention to this matter!" Contrary to Trump's assertion, Swift, a self-made billionaire, appears to be as successful and popular as ever, with herrecently announced next albumThe Life of a Showgirlanticipated tobreak recordsand seemingly the entire world talking about her upcoming wedding. Contact usatletters@time.com.