Not exactly "help I spent too much" but I did have an acquaintance from middle school post a pretty tone-deaf request for help. She had attended an elite US university for undergrad and then gotten a masters from an elite English university (both in English Lit, I think). Apparently, at some point she met a guy and the relationship was serious enough for her to follow him to a different country while he finished up doctoral studies (in engineering or science, I think). She wasn't fluent in the non-English local language, and unsurprisingly there wasn't much job demand for some with a BA and MA in English there - so the best job she could find was working as an au pair. He wasn't making much either, PhD stipends were small and he was supplementing with an under-the-table paying job working nights. Basically, the two of them had almost no money after basic expenses were paid (rent, food), or at least I could believe it with the info on how little they made.
Her request for money was to get documents translated so she and her boy could get a fiance visa for him to come back to the states with her - not a totally unreasonable request, but her post had this subtext, more or less: "student loans are crushing me, there are no jobs even for people with elite degrees, in no way is my poor financial situation at all my own doing." Seriously, get a better job somewhere else while he finishes school and accept that you'll be long-distance as a couple. Or recognize that choosing to live in a country where you don't speak the local language fluently is going to severely limit your earning potential and might therefore limit other options. Or recognize earlier on in your life that career prospects should factor into your decisions to take on six-figure debt loads (she also mocked some business recruiters during her senior year of college as "Bimbos in high heels"). It's not like it's a secret that there aren't many high-paying jobs that require an English degree (especially when the local language isn't English). I was actually considering donating to help (I'm a sap, what can I say) until I read the description and got so disgusted by the lack of recognition that she had made any sub-optimal choices (financially, at least).