"Cry Pretty" by Jason Eady is a song about a chance encounter between two former lovers who haven't seen each other in a while. The protagonist acknowledges that it has been a while since he has seen the girl, and it's ironic that they meet in a place like this. He mentions that he has someone waiting for him outside, implying that he has moved on and is in a new relationship. Despite the circumstances, he remarks that she looks just like he remembers her, and regrets how things turned out between them. He notices a familiar look in her eyes, which he had seen when she left him. The song suggests that he still thinks about her occasionally and wonders what could have been if it were a different time. The chorus of the song focuses on her ability to cry beautifully. He acknowledges her strength and grace in handling her emotions, complimenting her ability to cry without leaving a trace. However, it also hints at her sadness and the pain she may be enduring. As the song progresses, the protagonist decides it is time for him to leave, urging her to understand and assuring her that she will be fine without him. He suggests there is someone out there she can turn to, encouraging her to keep her head up and reassure herself. In essence, "Cry Pretty" explores themes of lost love, regret, and the complexities of moving on. It reflects on the bittersweet emotions and memories that can arise when encountering a past love, as well as the resilience and beauty in someone's ability to handle their emotions.
