I love that this guess makes perfect sense and is a thing that could 100% happen at some point in the show, but also is completely wrong because the real context is so balls-to-the-wall unhinged that no-one without the context, could ever guess the actual context of what's happening right now.
The context for the curious, because I know there are folks out their who think their show is weird, but isn't:
Due to a brief interaction with a time machine in a previous season, one of the characters, Donut, became temporally unstable and was scooped up by an ancient and immortal being imprisoned for all of time who is pretending to be God in order to convince Donut that they needed to be freed, and thanks to shenanigans involving time portal guns, the main characters saved their friend, Agent Washington, from a bullet to the neck (that left him with brain damage from oxygen deprivation) causing time to split into a paradox giving the immortal being's minion a chance to go ham and start shattering the time stream in order to break the eternal prison, but because Donut has become space/time!jesus he is immune to the paradox and is able to travel into the paradox and find Washington and restore his normal timeline memories but then they realise they're going to need the help of the rest of the main characters, The Reds and Blues and Carolina, in order to set things right, because "reasons" they decide the best time to give everyone back their memories is during the Blood Gulch era (early series), which means the only person not together is Carolina, because she was off being presumed dead and Wash needs to find out where she was during that time so he can go get her and bring her to the rest of the group and he reasons the best way to find that out is to travel back to the Freelancer era (preseries), and ask her there, only they weren't that close and after a long montage of being viciously rejected every time he tries to ask Carolina where she might go if she had to ditch the project and fake her death, Wash breaks down and confesses everything to his friends, the Triplets, because he's at his wits end and if he doesn't get this info the universe is doomed, and then one of the Triplets, Iowa I believe, asks why Wash didn't just go to a point in time when he and Carolina were already friends in order to ask her when she'd be more likely to answer the question, which makes Wash die inside that he'd missed the obvious solution for so long before he heads back to the future where we have ^ this ^ scene ^.