Jake regrets that he never spoke to the young woman, so he imagines what life could've been like with her. He just watched her, and she recalls how unsettling that was. The young woman and old Jake have a confrontation at Jake's high school in the I'm Thinking of Ending Things ending, where she shares that Jake never approached her at the bar. As revealed in the I'm Thinking of Ending Things ending, he did see her from afar years ago at a bar, but he never mustered up the courage to talk to her. That's because she's technically a figment of his imagination. Jake refers to her by different names, he changes the story of how they met, her career constantly switches, and her childhood is even altered a bit. Throughout I'm Thinking of Ending Things, the young woman's backstory constantly changes. The young woman is not Jake's girlfriend, but rather a woman he admired years ago. Since he can't, I'm Thinking of Ending Things sees old Jake imagining life with his parents the way he wishes it could have been.
Whether he wishes he had more time with them or could've had a do-over with the time they did share, he clearly thinks about whether there was something that he could have done differently in regard to their relationship. It's unclear when his parents passed in relation to where Jake is in the present timeline. The final sequence with his parents shows his mom at the end of her life and unable to care for herself, with his dad barely functioning. Jake's dad looks physically unwell, and his mom appears to be mentally unwell. Clues are scattered in the sequences where they're middle-aged the fact their health is starting to fail. While he and the young woman are visiting his parents, they are shown at different times in their lives - middle age, as younger adults, and then near the end of their lives. Jake's relationship with his parents may also run deeper than that.
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