Boyfriend getting a job

Hi! So to start my bf and I are long distance while I am in grad school. We are 25 and eventually plan to get married but both need to have steady careers and accomplish our goals first. My boyfriend graduated from college in 2019 and delayed applying for jobs since his family went on a month long trip to Europe his plan was to apply to jobs in the fall and hopefully have something by the spring but then covid happened (out of control). During this time he was working for his family business making more $ than his friends who graduated, and was still making money during the pandemic which compared to a lot of people who had jobs close/got laid off was a plus. Well then he started his masters degree and due to covid that was all virtual. Well now it’s almost 3 years since he graduated and he’s still doing the same thing working for his family business. I have helped him from reading his resume, sending jobs, helping him reach out to recruiters and nothing is working. He is trying so hard and 2 weeks ago had a perfect job for entry level people, doing sales no experience and emailed the recruiter, got 2 interviews sent a thank you and got declined when they said they were hiring multiple people and he told them he could start and move in 1-2 weeks (even though it’s still remote but they plan to open up again soon. I was shocked since like this sounded like the perfect job for him and they keep posting they are still hiring. He keeps applying to places but honestly even with his bachelors degree all the entry level jobs require experience and he even has reached out on LinkedIn to people asking if they have any openings and just gets negative messages back. Idk what else to do since I’m frustrated, he is frustrated and it’s like nothing works out. Truthfully, he’s open to jobs anywhere and like there’s nothing that seems like a good fit even though he applies to everything. I know he’s lucky to have his family business, and lots of people are struggling with jobs but this was an issue even before covid. He will have his masters soon but I don’t even think that will help him. Any advice?? It just feels like everyone has a job and Ik getting tired of hearing him talk about applying and people asking me if he has a job yet it just have been dragging on too long. And I hope once he gets his foot in the door he is good but it scares me that this will how it always will be