Maybe you need to try out more powerful dynamic languages? I mean even Python has 'pdb' which gives you a fairly authentic gdb experience, and you can always dir() and help() something in the REPL. For me I find myself not missing a debugger very much at all in Python code, whereas Java code of a certain size and legacy history forces me out of my preferred vim world and into Eclipse for the interactive debugging alone, the language makes it more painful to debug in other ways you can get away with in say Python. Plus I find that language culture matters. Java programmers will assume you have a big IDE and debugger and will write their code accordingly. Other language cultures do something different. Occasionally you'll get principles like "grep-friendly code" in an effort to cut across cultures but they're still not universal.

Clojure is another example of a pretty decent experience, e.g. "add-watch" is built-in, it has a REPL (so I've used it to debug Java code before), and the coding culture is functional programming which has its own benefits for debugging. Common Lisp is even better, it's a system as much as a language and so the runtime itself has all the debugging capabilities that you need a heavy IDE for in simpler non-system languages. (break, compile, trace, update-instance-for-redefined-class, object field inspection, extendable print-object methods are all there part of the standard, lots of introspection and redefinition capability, and CL compilers like SBCL can give quite detailed type, argument count, typo alerts, cross-reference usage, and optimization information at compile time, still no IDE needed (though editors like emacs/vim have nice wrappers and can automate some stuff). Check out this short series: https://malisper.me/debugging-lisp-part-1-recompilation/ )