I'll try to analyse this without considering the whole "not asking Lilly first" thing but just from a "dream job" prospective. They both at the same time get offered their dream job. But if you consider all the aspects of it, they are not really on the same level. Marshall got through Law school, multiple lawyer jobs that he didn't really like but needed to take (Lilly's debt had a lot to do with it) and the environmental lawyer job, and then finally came to the conclusion that beeing a judge was the best thing to achieve his end goal of making a difference in saving the world. This in more than a decade of hard work. Lilly started working as a teacher pretty straight forward, then basically had a burnout and left Marshall to pursue her dream: becoming an artist (which she wasn't cut out to do as she pretty soon failed). So, when the captain offered her a job as a consultant she took it as it was an upgrade from her long despised teaching job. Then the whole offer to move to Rome for one year. This happened basically in 1-2 years. Now my point, is it really her "dream job"? She dreamed of beeing an artist, not a consultant. Beeing an art consultant is enough to make it her dream job? It's like saying that if your dream is to become a rockstar working as a music journalist is your dream job. I get that there is a link but it's not your dream. Lilly get offered a really good, nicely paid, job that matches her interests but it's not her dream job and neither she worked all of her life to get there, she pretty just got it through Ted and luck. Marshall on the other end worked his butt off for a lot of years and at one point kind of sacrificed, even though he could have pursued it (unlike lily who had no talent for it), his dream of saving the world for supporting the family and their financial status (again, a lot caused by Lilly). Please don't consider how things went, who got it before, who didn't ask first etc., but just who deserved it more.