I sometimes like to imagine what really happened to Ron Weasley later in his life. Once the dust has settled and everyone is getting on with their lives, graduated and adults stepping out into the adult world. Harry is, of course, fine because he's already stupidly rich. Ron, however, not being conveniently wealthy, has to get a job. He hopes to one day be a wizard chess champion and would love to do that for a living, but he has no idea where to begin and that dream won't pay the bills. He asks his father to help him get a job in the ministry, but Arthur Weasley is working hard to destroy corruption in the ministry and probably has a good career ahead of him at last - he can't risk appearing nepotistic at this delicate point in time. So Ron tries out for the only other obvious job for wizards - teaching. But while Ron has his talents, he's not an impressive wizard and although he has a lot of hands on experience in Defense Against The Dark Arts, there's a plentiful list of substitute teachers and casual teachers with more classroom experience than Ron. Plus, with such a high student death count over the last few years, Hogwarts has seen a big drop in new enrollments and they're struggling to pay the staff they've got at hand. Disappointed, Ron sets his sights lower. He tries waiting tables, just to pay the bills, and gets a job as a sales clerk in Olivanders. But as Hogwarts lacked even the most rudimentary maths or economics classes, he's constantly counting out people's change on his fingers and he doesn't last long in the customer service industry.
During this time he starts seeing Hermoine - who being naturally brilliant all her life, has already landed a promising career in the wizarding world. Ron realises that while he might fail at everything else, Hermoine is the best thing that's ever happened to him. He asks her to marry him and she says yes. But having already borrowed money off his good friend Harry just to live, and unable to ask his eternally-financially-struggling parents for any help, Ron takes out a sizable loan from the bank to buy the engagenemt and wedding rings and to pay for the wedding. After they're married and they are living together, Hermoine discovers the massive amounts of debt and financial hardship Ron is under. This is their first argument as a married couple and, taking place in the early days of their life together, becomes a sore point they return to again and again over the years, always growing like a cancer on their relationship.
And after all this, Ron still can't hold down a steady job. He gets short term work, contract work and casual positions here and there, but many of them barely cover the cost of his uniforms and the floo powder he uses to get to work. It doesn't take long for depression to sink in. Ron constantly compares himself to Harry, who is now marrying his sister and still living in luxury, and even to his own wife, whose constant triumphs vindicates all the time she spent studying. Even though it's her success that pays their bills, Ron resents himself for being unable to take care of his family - like his father did - and comes to resent Hermoine for not even allowing him that small success in life. A friend of Ron's father eventually gets Ron a job as an apprentice fireplace maker or something, which Ron takes and does his best at. But he's got no passion for the job and, being accident prone all his life, struggles to find any success. Hermoine is now pregnant - they both know it's unplanned and probably the consequence of post-argument make up sex. Ron realises that's the only time they're ever intimate anymore and now that she's with child, and determined to keep it, he'll forever be trapped in this loveless, hopeless marriage with a woman he resents more and more each day.
It's been years since he even looked at a Wizard Chess board and sometimes struggles to remember the rules. There isn't a single wizard in the world with a degree in psychology, so Ron's depression goes unchecked. He eventually learns to be complacent, settling into life as a husband to a woman he hates, father of a child he knows he'll just disappoint, and always playing "Keeping up with the Potters" so Harry will stop looking at him like he's some kind of fucking charity. Hermoine has another child. He's not sure if it's his. It's not impossible, but its not likely. As it grows up, sometimes he wonders if it doesn't look a little like Harry. He doesn't really care either way. Ron stops seeing his family, eventually stops seeing his friends and only talks to his wife and children out of necessity. He snacks a lot and drinks a lot in his spare time. His workmates whisper "alcoholic" behind his back but he doesn't care. Although the anger and resentment never ends, the booze doesn't make him violent. Violence demands a passion that Ron will never know again in his life, maybe never did know.
At the age of 65, Ron dies of a heart attack. A small funeral is held. He's got few friends left who bother to show and only a handful of family members he hasn't pushed away. He's cremated and Hermoine keeps the ashes, storing them in the attic until she gets a big promotion at work, moves into a bigger house with her children and "forgets" to pack the urn containing the remnants of her late husband. The new tenants find it and promptly throw it away as they're moving their stuff into the new house.
I sometimes like to imagine what really happened to Ron Weasley later in his life. It's kind of weird.