Sometimes second chances don't work out!

Ariana Grande and boyfriend Jai Brooks have called it quits again, Us Weekly reports.

"It has not been an easy few months," a source tells the mag of the "Problems" singer, 21, who recently lost her grandfather. "Jai just wasnt as supportive as he could have been," the source adds.

The pop star took to her Twitter and posted a cryptic message after news of the split broke. "You learn a lot about love, life and the people around you during a time of crisis. July was painful for many reasons but of all the personal loss I suffered last month, the loss of my grandfather, a true gentleman, was the only one that truly mattered. I thank everybody who was here for me when I needed them as the ones who weren't really broke my heart. August is about to be a beautiful, beautiful month. Looking forward to all the good coming up," she tweeted.

The pair began dating in August 2012, called it off a year later, and then reunited last May.