As we see, most of his bleating and wailing that isn't due to his irritating habit of thinking that he's being tricked into doing something just because he feels uncomfortable and has also lost control of the situattion is due to his whining that he can't get married because he still has the ability to enjoy life and is still grateful to be alive when he gets up in the morning. Only when he's too old and miserable to actually function can he bite the bullet and get married because his life will be one of unrelieved misery anyway.
This, of course, is because he has a distorted view of what family life is because the only married couple he actually ever associated with that any of us know of are John and Elly. This means that if he'd had a wider sample base, he'd have realized that Elly is both a statistical outlier and also still the same yowling stick-in-the-mud playing the martyr card she's been since Jim and Marian had a child who they let win all the time despite what her lying eyes told her. The end result is that he wouldn't be making ignorant yappity-yap about setting down roots only after he's gone to seed because he'd have been exposed to competent, confident happy people who actually know how to live their lives.