Give him a chance to step up or is he just a mooch?

I just want some perspective on the relationship between my best friend (F32), lets call her Jill, and her boyfriend, Darren (M38) of 5 years. Before Darren and Jill moved in together 3 years ago, he worked for his family’s restaurant for over a decade but when they retired and the restaurant shut down, he had no more work. After moving in together, he had an online business that has now failed and probably never made much money in the first place. He recently picked up a part-time retail job but refuses to take on more hours even though he was offered a promotion. He has a Bachelor’s in business but doesnt do anything with it. It’s like he wants to earn just enough to cover his personal expenses and wont make more effort to earn more.

Darren does regularly take care of household chores, cares for the dog, and does some cooking. However, he had to be told to do all of this, and was apparently okay with gaming 24/7 instead of doing anything for a while. Recently, Jill confided in me that he never contributed to the mortgage (which is very low because the house is owned by Jill’s mom) or anything other than the cellphone/electric bill. When she asks him to step up more, he says “you expect too much of me”.

Part of me wants to have sympathy for Darren because my dad went through a long stint of unemployment/underemploynent after the 08 Recession but I could never call him a slacker. Where my dad couldn’t contribute financially, he contributed by being the best stay at home dad he could be. The he handled cleaning, shopping, childcare, house repairs, and did it all without ever being told to do so my mom could just focus on work. My dad even went back to school to change his career. Because of this, I don’t subscribe to the belief that men have to be the primary breadwinner but instead, both parties in a relationship have to contribute something of value to the household.

But Darren is doing none of these things…to be frank he basically acts like a child who has to to be told to chores. He seems so nice…just unmotivated and kind of lost in life. Part of me wants to believe he’s depressed, because unemployment does take a toll on mental health. He also worked for years at family business he probably thought would stick around and tried to run his own business and failed. But we could all be duped and he is just a lazy and selfish mooch.

Next time Jill and I talk, should I advise her to keep pushing him to step up more? Or should I encourage her to kick him to the curb for not contributing anything significant to the relationship? When do you know when you should wait it out or end it?

TLDR: Possible slacker boyfriend doesnt want to work more hours to financially contribute and has to be told to contribute to the household in otherways. I feel sympathetic because I suspect he has depression. But is he just a mooch?

Edit: Y’all Jill has asked me for advice on this matter, and we talk about it frequently. Sorry that its not my issue, but my personal romantic relationship is solid, and I have never experienced this problem before. I just wanted to see how others take on this situation.