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Help I Sexted My Boss often has grizzly listener stories that are enough to make anyone cringe, but a recent episode has proven too much even for hosts Jordan North and William Hanson. The duo were left in silence when one woman emailed in with a predicament that saw her not only find and use an NSFW object under her mum's bed...but later discover it was modelled off her dad. "I think we're done", North says, fighting tears. Sign up to our new free Indy100 weekly newsletter

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Singer Ariana Grande is no stranger to heartbreak after news broke that she and her husband Dalton Gomez have separated after two years of marriage. Since their separation, dating rumours have already begun to swirl, controversially linking Grande with her West End co-star Ethan Slater who also went through a very recent breakup. Sign up to our free Indy100 weekly newsletter Many of Grande’s former flames have been those in the entertainment industry, including comedian Pete Davidson and musician Mac Miller, ranging from flings to engagements. Here’s a timeline of all Grande’s relationship history: Graham Phillips Grande and Phillips, an actor from The Good Wife, met when they were 15 after the pair starred in the Broadway show 13: The Musical together. They dated between 2008 and 2011 and wrote a song together called “Stick Around”. Ariana Grande and Graham Phillips - Stick Around LYRICS www.youtube.com Jai Brooks In August 2012, Grande and Brooks, the star of the Australian YouTube comedy group The Janoskians, began dating but broke it off in October of the following year. Around the breakup, Brooks accused the singer of cheating on him with her next flame, writing on Twitter, “Yes I was cheated on. Yes it does suck,” adding, “Yes I was left for another man”. Grande accused him of lying, responding: “Woke up this morning in complete and utter shock …I guess I shouldn't be so surprised. You said to me if I didn't come back to you, you'd make me look bad to the entire world. She added: “I’m no longer afraid of you or your lies anymore.” The pair briefly got back together in May 2014 but it didn’t last longer than three months. Nathan Sykes According to US Weekly, Nathan Skyes, from the British boyband The Wanted, and Grande began dating in August 2013, while she was reportedly still with Brooks. It came after the two performers recorded the song “Almost Is Never Enough” which featured on the soundtrack of the film The Mortal Instruments: City of Bones. The relationship was short-lived and a source told the publication they “hardly ever saw each other”. Ariana Grande - Almost Is Never Enough ft. Nathan Sykes www.youtube.com Big Sean In October 2014, Grande confirmed the speculation that she was dating the rapper Big Sean by saying that he was “one of the most amazing men in the whole world”. Big Sean’s late former partner Naya Rivera, who was also engaged to the rapper before their split in April 2014, claimed that she found Grande at their home while she and Big Sean were still dating, in her book Sorry Not Sorry. Grande and Big Sean’s relationship ended in April 2015 eight months after it began. Ricky Alvarez In the summer of 2015, Grande and backup dancer Ricky Alvarez were first linked. It was during their relatively short-lived relationship that Grande was caught on CCTV licking a doughnut on display in a shop and saying that she “hates America”. By July 2016, the pair had broken things off, despite Grande telling Billboard magazine in May, “I’m a very happy girl.” Mac Miller Grande dated the late rapper Mac Miller, whose real name is Malcolm McCormick, between 2016 to 2018. They broke up in May and Grande took to Instagram to open up about their break-up. Grande wrote: “I respect and adore him endlessly and am grateful to have him in my life in any form, at all times regardless of how our relationship changes or what the universe holds for each of us!” In July 2018, Mac Miller shared his side of things, explaining in an interview: “I was in love with somebody. We were together for two years. We worked through good times, bad times, stress and everything else. And then it came to an end and we both moved on. And it’s that simple.” The rapper died in September 2018 and Grande issued a heartfelt tribute. She wrote: “I adored you from the day I met you when I was nineteen and I always will.” Pete Davidson Comedian Pete Davidson and Grande were first linked in 2018, with Davidson confirming their relationship in May 2018 with an image of them dressed in Harry Potter costumes with the caption: “The chamber of secrets has been opened.” Just one month later, it was revealed that the pair were engaged, with Davidson reportedly popping the question with a $96,000 diamond ring. But, in October 2018, it was reported the couple had split, with a source saying they realised they moved too quickly. Davidson said: “She’s a wonderful, strong person, and I genuinely wish her all the happiness in the world.” Mikey Foster Performer Mikey Foster and Grande first sparked dating rumours in August 2019 with the release of her music video for her song 'Boyfriend' in which they kissed. In 2020, a source confirmed the pair had actually been dating since June 2019 before their relationship fizzled. Dalton Gomez Grande and her future husband, the real estate agent, Dalton Gomez met in 2020 after she hired him to help her find a house to buy prior to the outbreak of Covid 19. The relationship wasn’t publicly confirmed until May 2020 when the pair were pictured slow dancing in the music video for Grande and Justin Bieber’s track, 'Stuck With U'. In December 2020, the pair announced their engagement with Grande posting a picture of the diamond and pearl engagement ring on Instagram with the caption: “Forever n then some.” Grande’s rep told US Weekly that they got married in May 2021, saying: “It was tiny and intimate — less than 20 people. The room was so happy and full of love. The couple and both families couldn't be happier.” But, in July 2023, it was revealed the couple had “separated”, with rumours they had split as early as January 2023. Ethan Slater This month, it was reported by US Weekly that Grande is now dating her Broadway co-star Ethan Slater after the pair grew close during their London run of the musical Wicked. A source said: “Ariana and Ethan have only recently begun seeing each other but they have a lot of fun together and are enjoying each other’s company.” Their relationship has been seen as controversial by some, since Slater and his wife Lilly Jay only celebrated their fourth wedding anniversary in November 2022 and welcomed a baby boy in the same year. According to reports, Slater only filed for divorce from James on 26 July. In an interview published on 27 July, James told Page Six: “[Ariana’s] the story really. Not a girl’s girl,” adding, “My family is just collateral damage.” Have your say in our news democracy. Click the upvote icon at the top of the page to help raise this article through the indy100 rankings.

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