Carly Rae Jepsen's song "The Loneliest Time" tells the story of a past relationship that ended abruptly and left the protagonist feeling lost and lonely. The lyrics describe the feeling of being unable to move on from the relationship and the longing to reconnect with their former partner. The song begins with the protagonist having a bad dream about being on their ex-partner's street. They mention quitting smoking but admit that they are still unable to get over the breakup. They feel like their ex is looking right through them, reminiscent of a tragic Shakespearean love story where their relationship was left unfinished. The protagonist expresses their desire to see their ex again and reminisce about the past. They yearn for the look in their ex's eyes and describe the loneliness they have experienced since the breakup. They think about the possibility of rekindling their love and wanting to rewrite their story, hoping that it will finally be different this time. They mention having more bad dreams where their ex is out of reach, only able to see their shadow. The lyrics hint at the ex speaking words that left an impact and needing time to unpack their meaning. They suggest saving apologies for another time and believing that this time they will get the relationship right. In the chorus, the protagonist declares their intention to come over and knock on their ex's door, hoping for another chance. They express their desire for that look in their ex's eyes as they have been through the loneliest time. They contemplate the possibility of being together once more, rewriting their history. The song concludes with a bridge and a different perspective. The narrator reflects on their previous achievements, comparing it to reaching the moon but feeling lost in space. However, they express their determination to come back for their ex and make things right. The repeated line "And in the morning, Sun hits the water, Is this nirvana?" suggests a longing for a state of perfect happiness and peace. Overall, "The Loneliest Time" explores themes of longing, nostalgia, and the desire to reconnect with a past love. It portrays the protagonist's yearning to rewrite their story and find happiness with their ex-partner once again.