The legal OTC dose is smaller than the prescription dose because at the higher doses it's much easier to get in trouble, and it matters more what other meds you take. But I've also had doctors tell me to take 3 or 4 ibruprofins at a time.
There are lots of OTC medicines that can be addictive (like a lot of cold formulas, for instance) but I've never heard of anyone getting addicted to (or feeling loopy from) OTC pain killers, ignoring the codiene ones people smuggle in from UK countries, which are addictive. But it's easy to develop a tolerance, which means you need to take more of the drug to get the same pain relief. Unfortunately, you don't necessarily develop a tolerance to the side effects, in fact, this is the usual way people get in trouble with kidney damage, etc. So it's possible your friend doesn't have extraordinary pain, but just a really weak response to OTC pain meds. Of course, it's also possible that he has extraordinary pain from cluster headaches, migraines, a brain tumor, or something else. Either way, he really ought to see a doctor for diagnosis and pain management. He should definitely shop for a doctor he likes, since he's not likely to got any benefit from any other kind of doctor (Even if that doctor is terrific.)
Listerine - good luck with your pain. Advil and Aleve are very similar drugs, so taking both is similar to taking an overdoes of one. Aspirin is related (not quite as closely) to both of them, which is why doctors never advise taking Aspirin with either of them. Tylenol is a little more different, and is often recommended with Advil for really bad pain or fever, at least for short-term stuff. Again, good luck.
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