Angelina Jolie, Drake
Angelina Jolie (L), DrakeDia Dipasupil/Getty Images | Michael Loccisano/Getty Images for TNT

Drake is not afraid to make the first move and especially if it is a Hollywood A-lister.

Nobody has forgotten his rumoured fling with Jennifer Lopez, Rihanna and even tennis ace Serena Williams. Not the Hotline Bling crooner seems to be quite desperate to try his luck with another popular Hollywood actress Angelina Jolie who is currently single after his split with estranged husband Brad Pitt.

Also read: What! Loung Ung has taken Brad Pitt's place in Angelina Jolie's life?

On Thursday, the singer took to Instagram to share a very dramatic photo with a witty caption. In the photo, Drake is seen sitting alone at a table as he was looking glum.

Captioning the photo, he wrote: "Stood Me Up."

The 31-year-old even tagged Angelina Jolie in the photo. As the Salt actress is officially not on the social media platform, hence the singer tagged a fan site of the actress which has a huge fan following.

Check the picture below.

Stood Me Up

A post shared by champagnepapi (@champagnepapi) on

It is very Drake-y behaviour as the singer is no stranger when it comes to pursuing Hollywood's leading ladies.

Fans took to various social media platform to comment on the picture.

One user wrote on Twitter: "LMFAO drake just took flirting to another level. Angelina jolie."

Another user commented on the Instagram photo: "Probably deserved it!" while another wrote, "The drakest caption ever."

Rumour has it the rapper was romantically involved with Amor songstress Jennifer Lopez in 2016. The hitmaker later took to Instagram to share a very cuddle picture of them. Sources said at the time that the mother of two seemed to be "smitten" with him.

It did not go well and ended abruptly following a very short period of time while a source close to the rapper told PEOPLE things between them were "never very serious."

"They like one another and had fun together," the source said.