Ariana Grande's dating timeline involves many high-profile boyfriends including rapper Big Sean, late Mac Miller, and comedian Pete Davidson. The 27-year-old singer has been in Hollywood for more than 15 years. She made her debut in 2008 with Broadway musical 13 and then moved to TV to play Cat Valentine in Nickelodeon's Victorious in 2010. After ending her 5 months engagement to comedian Pete Davidson, Grande wrote an ode to all her exes in her chartbuster Album 'thank u Next'. Now the singer has moved on from her past as recently Grande announced that she is engaged to current boyfriend Dalton Gomez with a series of pictures of her and her fiancee that she posted on her Instagram account. So let's take a look at the very well-known relationship past of Ariana Grande, from her long term relationship with late rapper Mac Miller to her surprising engagement and more surprising break up with Saturday Night Live comedian Pete Davidson.

Graham Phillips (2009-2011): Back when Ariana was just a teenager, she dated actor Graham Phillips for more than 3 years. She first met Phillips during the filming of Broadway musical 13. Ariana made their relationship official by posting a picture on her Instagram.

Jai Brooks (2012-2014): During the early stages of her music career, Ariana had a long-distance relationship with Jai Brooks. Jai Brooks was an Australian YouTuber who started a competition with his brother to see who could get her attention, which the singer's mum spotted and told Ariana to message him! They dated for more than a year but it all ended when Brooks publicly accused her of cheating on him with Nathan Sykes, something she has strongly denied saying Brooks is just trying to get a '15 min fame'.

Nathan Sykes (2013): In the five-ish months that Arianda and Brooks broke up, she started dating Nathan Sykes the singer of the British Boy Band The Wanted. Grande first saw Sykes on a red carpet in 2013 but they never met properly until months later when they united to film a music video for their song "Almost is never enough". They both started dating when they collaborated again for the opening act of Justin Bieber's Believe tour later that year. They both dated each other for almost 5 months but the strain of the long-distance relationship forced them to split up in 2014.

Big Sean (2015): Ariana Grande's next relationship came in 2015 when she started dating rapper Big Sean. The two first met when they collaborated on Grande's song "Right There" from her first studio album "Yours Truly". After months of dating rumors, the two made their relationship official by making their debut as a couple at the 2015 Grammy awards. According to a report by E! News the couple broke up because of their heavy work schedules. Both artists planned to be on tour for the next year, which would make it hard for them to be together.

Ricky Alvarez (2015-2016): After Big Sean and Ariana broke up, the singer started dating backup dancer Ricky Alvarez. They started seeing each other in 2014 but their relationship became official when they kissed during a live show in 2015. Ariana and Ricky dated for just over a year before she tweeted 'life is wild and change is f***ing fantastic' and hinted that the couple's relationship had come to an end. The couple was caught up in an infamous scandal after they visited a doughnut shop and were filmed secretly licking doughnuts, quickly being slammed by both fans and the press, before issuing a public apology on Twitter.

Mac Miller (2016-2018): Mac Miller, Ariana's most high profile boyfriend before she dated Pete Davidson. The story of Miller and Grande go way back to 2012, when they both recorded a cover of "Baby its's Cold Outside" for Ariana's Youtube channel. A year later Ariana released her debut single "The Way" featuring Mac Miller. The official video for "The Way" featured a kiss between the two singers. The singer denied that the two were romantically involved at the time, saying that the kiss was scripted and the two are just friends. In 2016, 4 years after the release of their song, Ariana surprised everyone when she was seen kissing Miller outside a sushi restaurant in Los Angeles. After that Miller dropped a music video for his song "My Favourite Part" featuring Grande in it. Later in 2016, Miller even joined Grande on her tour. The couple announced their split up in May 2018, though neither of them has revealed the actual reason for their break up.

Pete Davidson (2018): In what had been a total whirlwind romance, SNL comedian/actor Pete Davidson and Ariana got together after spending time together. She appeared on the comedy show in 2018, telling her tour manager, 'I'm going to marry that man' after working in the writers' room with him. The pair quickly became inseparable before confirming their engagement just weeks after getting together and she dropped a whole track titled 'Pete Davidson' on her album, 'Sweetener'. However, after a matter of months of being engaged, Ariana and Pete split and Pete even deleted his Instagram account fuelling the rumors that it hadn't ended on good terms.It's been suggested that the death of Mac Miller and its effect on Ariana played a big part in the couple's split. However, that has remained unconfirmed as the pair has remain silent on the reasons behind their split. Although Grande pointed out in a 2019 interview with Vogue it was 'never going to last'. She touched heavily on the split in her album 'thank u, next' with tracks 'In My Head', 'Ghostin', and of course, 'Thank u, next', so if you want any more tea, have a big ol' listening party!