Justin Timberlake and the Tricky Art of the Breakup Text

Britney Spears recently revealed in her upcoming memoir, The Woman in Me, that Justin Timberlake, her then boyfriend of two years, broke up with her via text. This breakup reportedly left her devastated, whilst Timberlake was seen “happily running around Hollywood” enjoying the success of his ever-growing career. In a moment where many are reflecting on the poor treatment of Spears both professionally and personally, is it time we re-assess the acceptability of the break-up text?

Spears and Timberlake first met in in 1992 on the set of the “The Mikey Mouse Club”. Officially, they began dating in 1999 when Spears was 17 and Timberlake was 18. After three years, a shared Super Bowl performance and the most iconic double-denim look of all time, the pair called it quits after cheating allegations surfaced on both sides. At the time, Timberlake famously responded with his single “Cry Me A River” featuring accusatory lyrics about a cheating girl and an actor who looked suspiciously like Spears. In an excerpt from her memoir, Spears described how the media reaction to the music video left her “comatose” and details about the break-up itself are only emerging now. 

Citing the director of Spears’ 2002 music video “Overprotected: The Dark Child”, The Independent are reporting the break-up text sent by Timberlake allegedly consisted of two words: “It’s over!!!” Naturally, Spears is not the only celebrity to have had a high-profile relationship end over the phone. Taylor Swift told Ellen DeGeneres that in 2008 Joe Jonas broke up with her during a 27-second phone call: “That’s got to be a record,” she told the host. Cazzie David, meanwhile, writer and daughter of Larry David, revealed that Pete Davidson broke up with her via text following a two-and-a-half year relationship. Zayn Malik famously sent an engagement-ending text to Little Mix’s Perrie Edwards, who described the break-up as “the worst time of my life”.

So if the repercussions of break-up texts are so obviously hurtful for the recipient, why do people keep doing it? According to a 2020 Sky Mobile survey, nearly a third of Brits have been dumped by text message, whilst a 2023 Paddy Power survey found that 71% of Gen Z participants admitted to ghosting someone online. Speaking to Well + Good, therapist Daniel Olavarria has a more sympathetic take on the break-up text. Olavarria advises that when it comes to deciding how to end a relationship, those involved should “let the depth and substance of your relationship, and your personal safety, be the guide.” Ending a relationship via text is “perfectly suitable” if those involved have only been on “one or two” dates. Longer-term relationships, however, should sometimes be treated differently as ending them via text can “leave the receiving partner feeling confused, abandoned, and with an overall lack of closure.”

The break-up text may seem like a strange and potentially cruel product of our internet age but the reality is break-up messages have always existed – they just used to be sent in different forms. Consider Jackie Kennedy’s letter to her then teenage boyfriend featuring the immortal words “I guess I’m not in love with you”, or actor Richard Burton’s 1973 letter to Elizabeth Taylor: “You’re off, by God! I can barely believe it since I am so unaccustomed to anybody leaving me. But reflectively I wonder why nobody did so before.” He ends with the words: “I shall miss you with passion and wild regret.” 

With these lines, it becomes apparent that break-up message can be something of an art form. As language and technology evolves, it is only natural that expressions of regret and sorrow have found a new medium today. Though most break-up texts likely won’t achieve the poetical heights of Burton’s or Kennedy’s, writing break-up messages has become far easier particularly with the assistance of AI. Though I would strongly advise against using Buzzfeed’s “Break Up Text Generator” in a real-life situation, I did, out of curiosity, fill in the details required to assist a 21-year-old Justin Timberlake keen to end things with pop sensation Britney Spears. Answering the bot’s prompts as best I could (in response to the question “What do you have too much of in your house?” I filled in the blanks based off an online rumour that Timberlake has a secret love for sneakers), the results were as follows:

Hey Britney,

I hope you’re doing alright. Look, I think it’s time we have a serious conversation. I can’t deny the fact that I maybe, allegedly, saw you kiss your dance choreographer. Remember when we first met and I fell in love with your amazing singing? That’s what made me fall for you in the first place.

Thinking back, I should’ve noticed the red flags earlier. Like when you wore a deep denim at the American Music Awards instead of washed denim – a clear sign! But hey, lesson learned.

We’ll have to officially divide our sneaker collection and go our separate ways now. In the words of a famous pop song, “We are never, ever, ever getting back together” – Taylor Swift.

Wishing you all the best, and looking forward to finding someone who appreciates my sneaker obsession!

Peace out,


The results, as we can see, are far from perfect, but it sure beats ending a three-year relationship with a two-word text.