I would assume that being tasked with picking Taylor Swift songs to sing in front of Taylor Swift herself would be scary. In fact, when Sombr did it, he described the experience as “crazy.” However, after hearing him recall the story behind how he picked the tracks he sang for her and what it was like performing at her induction into the Songwriters Hall of Fame, I gotta say, it sounds pretty chill. Now, obviously, a task like this comes with immense pressure. Attention is always on Taylor Swift. With her wedding to Travis Kelce reportedly coming up, the blockbuster success of the Eras Tour and her consistently releasing new work, she’s constantly the talk of the town. So, performing her music is no small task, especially when it was for an event that honored her as a songwriter. So, it makes sense that Sombr described his experience singing for her at the Songwriters Hall of Fame like this while on The Tonight Show: It was crazy. I mean, it was really her night, and she wanted me, out of all the people she could have asked, to perform two songs to help induct her into the Songwriters' Hall of Fame.That alone is quite a tall order, but he also had to perform the songs, too. However, it actually seems like it was a pretty relaxed experience overall. To that point, after Fallon asked if the pop star gave Sombr songs to sing, he said “no,” and explained: So, basically, I was like, 'Taylor, what songs do you want me to sing? You know, this is your night.' And she was like, 'No, you choose.' So, I was like 'Seriously?' So that really put the pressure on. You know, she has such a vast discography of so many hits. So, I went through, I picked two songs, and I suggested them to her, and she was like, 'Perfect.'Ultimately, Sombr chose to perform “Dear John” from Speak Now and “Cardigan” from folklore. Both are well-known and beloved tracks from Swift’s discography, but also not her biggest hits, which signifies how thoughtful Sombr was in his choices. Overall, I loved the picks, and clearly the singer he was helping induct to the Hall of Fame did too. That was clear with her chill reaction to his picks in the first place. However, her reactions during his performance show how much she loved the choices too: @vanityfair ♬ original sound - Vanity Fair Overall, this story actually makes so much sense. While I know Taylor Swift is meticulous and very hard working, she also seems quite chill, all things considered – you can see both those things on display in her Eras Tour docuseries, which is available with a Disney+ subscription. So, I totally get why she trusted Sombr to pick the songs he wanted to sing himself. Plus, she’s made her love for the “12 to 12” singer very well known. For example, during an interview with the NYT where she talked about her career, lyric choices and more, she also explained why she loved Sombr so much. Specifically, she complimented how “intensely confessional” his lyrics are. Along with that, she said he’d be at the top of her Spotify Wrapped, which he reacted to on The Tonight Show. Based on those comments, I assume she’d be happy with just about any song he chose to sing. So, overall, this experience seems like a joyful and shockingly chill one. While Swift’s career and skill were being honored, she didn’t feel the need to help Sombr pick the songs he sang. She was just happy with what he chose.