Thanksgiving road trip sounds romantic until the itinerary starts sounding like a stress test. New boyfriend of three months wants a California to Colorado drive, a pickup in Nevada, a 3 a.m. departure, four days total on the road, and a first meeting with his kids, grandkids, and not‑yet‑ex wife squeezed around an intensive statistics class with quizzes and a final right after. The plan relies on car Wi‑Fi, homework in a moving vehicle, and studying in his son’s office while everyone else bonds over turkey.

The bigger picture makes the whole thing even more lopsided. Career change and that stats grade are tied directly to future income and the ability to retire at all, while the boyfriend already has a pension, a clear six-year countdown, and a prenup conversation on the table. He brings financial stability and a protected exit plan. She brings a second act that absolutely cannot afford a blown semester. Toss in the fifth anniversary of her father’s death and the fact that her own kids will now be in town, and suddenly this is not a fun adventure, it is a collision of obligations.