Since becoming one of the most prominent pop stars of today, Ariana Grande’s relationships have been some of the most talked about in the world of music. Having dated fellow high-profile musicians, an actor, and a YouTuber, it’s no secret that Ariana’s relationship history is one of the most fascinating in all of Hollywood.

Here are 5 men Ariana Grande has dated.

5. Graham Phillips

Ariana Grande began dating fellow actor and singer Graham Phillips back in 2008 when the pair co-starred in 13: The Musical. While together, the duo performed the hit song “Stick Around” and were seen together at the 2010 Emmy Awards (as pictured below). The pair broke up in 2011 after a three year relationship. Recently, Ariana and Graham reunited at the Red O restaurant in Los Angeles for dinner. Reports claim that the two stayed late into the night and had a wonderful time.

4. Jai Brooks

Sources close to Ariana say that she connected with Jai Brooks, an Australian YouTuber / prankster, in the summer of 2012 through Twitter. Despite living on different continents, their long distance relationship was kept active by texting and video chatting daily. The two finally went public with their relationship on October 7th, 2012 and met for the first time on New Years in New York City. After New Years, Jai and Ariana spent the next two weeks in NYC ice skating, bowling, and viewing the musical Wicked on Broadway. Here is a video of the pair making out right before his departing flight back to Australia!

3. Nathan Sykes

Ariana and Nathan, better known by their fanbases as “Nariana” began dating on September 24th, 2013. Prior to the start of their relationship, the pair released a duet “Almost Is Never Enough“. Sadly, Ariana and Nathan mutually decided to call it quits after just five months together. In late January of 2014, Ariana said in a radio interview that due to their busy careers, it would be best to remain close friends.

2. Big Sean

After several months of on-again off-again public speculation, Ariana finally confirmed on October 17th, 2014 that she was in fact in a relationship with rapper Big Sean during an interview with Telegraph Magazine. The pair were spotted on multiple dates together, most notably at the 57th annual GRAMMY Awards on Feb 8th, 2015. While together, Ariana and Big Sean collaborated on numerous songs together such as Right There, Problem, and Big Mistake. In April of 2015, US Weekly reported that the two split due to “conflicting tour schedules”.

1. Mac Miller

It is unknown how exactly Ariana and Mac Miller originally crossed paths, but in a recent interview with People, Mac Miller claims that their relationship “grew organically” over the years. The two have worked together on songs since 2012 and view each other as very talented artists. On July 15th, 2016, Ariana and Mac Miller were seen together at Disneyland and a few days later playing Pokemon Go. The first confirmation of a serious relationship sparked the following month in August when the pair was photographed kissing after a night out at a sushi restaurant.