the ex-boyfriend i'm still friends with:
dropped out of college
quit his job so he could go back to school years later (about the time we started dating)
moved back in with his parents
did not actually bother going back to school
was unemployed for a year with me supporting his lazy ass
got a part-time job at a gas station, but blew all his money on stupid shit and complained about not being able to save
got dumped by me about a year later
within a couple of months, he begged his dad to get him an interview for an IT position at his company. he didn't get the job (was narrowly beat out by a guy with a degree), but the interviewer was impressed enough to put in a good word for him at another office in a city a few hours away, where an incompetent IT just got fired. dude interviewed again, proved he could do it, got the job, and went from making $bullshit/hr to $70,000/year.
i still do not regret my decision to dump him, but i'm happy he went from a sad, sloppy mess to thriving in just the course of a few months.