Ellen Wouldn't Let Taylor Swift Forget This Awkward Confession From One Of Her First Talk Show Appea

September 27, 2024

Highlights

Taylor Swift has had some awkward moments on talk shows, including being insulted on Graham Norton's show and Ellen DeGeneres repeatedly bringing up an embarrassing confession.
During a 2008 interview on Ellen, Taylor admitted to driving past her exes' houses, which Ellen playfully brought up in subsequent interviews, never letting Taylor forget it.
While some appearances on Ellen have been more comfortable for Taylor, others have been more challenging, such as when Ellen pushed her about her dating life and tried to get her to confirm rumors. Despite these moments, Taylor continues to appear on the show.

Taylor Swift has always been a talk show favorite, appearing on all manner of shows from Graham Norton's The Graham Norton Show to The Tonight Show Starring Jimmy Fallon to Ellen DeGeneres' The Ellen Show. Yet not every interview has gone as smoothly as fans might have hoped.

Graham Norton couldn't keep Taylor Swift from getting insulted on his show, but in other scenarios, it's been the host who has wronged Ms. Swift. Case in point? Ellen DeGeneres couldn't let rumors about Taylor Swift's dating life lie — and kept bringing up an awkward moment through multiple interviews.

During A 2008 Interview With Ellen, Taylor Swift Was Put On The Spot

Taylor Swift admitted, via MySpace, to driving past her exes' houses

Though Ellen DeGeneres leaned into the awkward confession, Taylor Swift put herself in a tough spot by claiming on MySpace that she drove past her exes' houses.

While chatting with Taylor during her second-ever appearance on The Ellen Show (right before Taylor's first Grammy Awards appearance), Ellen joked with Taylor that she would have a hard time setting the singer up with anyone.

Ellen noted, "I'm scared to hook you up with anybody — even if I meet somebody great — because I hear something that you do that kind of frightens me a little bit. Let's... I'm going to give you a chance to clear it up. When you have spare time, you drive past your ex-boyfriends' houses. Why?"

Taylor replied, "I don't do that," while looking down and smiling. Ellen retorted, "Yes you do!" as Taylor elaborated on why Ellen thought that about her; she confessed it on MySpace.

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During the interview, Zac and Taylor decided to sing a song, which basically dissed Ellen for her interview skills.

Swift noted that she put that on her MySpace, but that "My MySpace is not like the typical Taylor Swift is blah blah blah so I wrote this bio on MySpace and it's actually — it's very honest about who I am as a person. I'm like 'in my free time I like to drive past my ex-boyfriends' houses."

Taylor mimicked typing as she explained that she's not "like throwing eggs," just "checking up on them."

Both the audience and Ellen seemed amused at that point, but Ellen also took the MySpace confession quite seriously. She teased Taylor, who called it an "act of public service" that she checked up on her exes.

Taylor finally ended the line of questioning by declaring, "Everybody does that, it's just nobody admits to it."

Ellen might have given up at that point, but she would bring up the drive-by tidbit in future interviews, never letting Taylor forget about it.

Ellen Wouldn't Let Taylor Forget Her Stalker-Ish Confession

On another episode of Ellen, Taylor Swift was reminded of her bad habit

As uncomfortable as her second interview might have been with Ellen, Taylor Swift returned many more times throughout the talk show host's run. Later in 2008, Taylor sat on Ellen's stage and admitted that Joe Jonas had dumped her during a brief phone call.

At the time, Taylor was promoting her album Fearless and admitted there was one song on the album about her most recent ex. Ellen brought up the drive-by factoid again during this interview while asking Swift whether she planned to drive by Jonas' house.

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When Ellen asked if that was going to happen with this ex, Taylor looked away before looking down. She raised her hands as if she was going to cover her face, then paused and said, "He's got a lot of security guards... they're big... so probably not."

Ellen then dropped the subject and instead asked Taylor about her other method of healing post-breakup: her music. The interview concluded without any more mention of Taylor's old embarrassing moment, but other interviews didn't go quite as smoothly.

Ellen DeGeneres Sometimes Charms Taylor (And Sometimes Drags Her)

Taylor Swift has appeared on Ellen many times, but not every appearance goes well

During some of Taylor's appearances on Ellen, the singer seemed to feel comfortable and respected. For example, during her second appearance on The Ellen Show, Taylor told Ellen that she would love to meet Justin Timberlake.

During a later episode, Ellen made good on her promise and brought Justin out to meet Taylor. But other episodes were not as fun for Taylor — namely, during an episode when Ellen pushed Taylor too far about her dating life.

Despite Being Called Out For Gaslighting Taylor Swift Ages Ago, Ellen DeGeneres Showed No Remorse

Taylor Swift is known for speaking her mind. Fans may have had more to say about her appearance on The Ellen DeGeneres Show than she did though.

It was widely interpreted as Ellen dragging Taylor when the talk show host tried to get Swift to confirm (by ringing a bell) which men she actually dated out of a pool of rumored beaus. Taylor flat-out told Ellen that she wasn't feeling very good about herself, and also defended herself when Ellen seemed to hint that Taylor was lying about not having dated Zac Efron.

While some fans are still unsure whether Taylor might have dated Zac on the down-low, Taylor wasn't having it when it came to Ellen inquiring about her love life. Even during a joking interview, Taylor's dating life was brought up once again as Ellen gave her fill-in-the-blank prompts like "I'm Taylor Swift and the last person I kissed was —."

Yet Taylor continued to appear on Ellen, perhaps suggesting that she and DeGeneres are friendlier than some of her on-stage appearances may suggest.

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