This is in my typical long winded form, sorry.
TLDNR version, buddy has gun issue, use the time fixing issue to talk about safety, buddy asks to watch him closer and help with mistakes.
You have gotten lots of really good replies, I can't really add too much more, but I will add I have the same kind of friend, not to that extent, but just a little rough around the edges....
Story time.
Me and this buddy are out in back of the house shooting and BS'ing.....you could look at shooting as an excuse to BS as generally more yacking goes on then pulling a trigger. He practices good trigger as well as muzzle ddiscipline but catching something that is not quite right....nope. We are standing side by side banging away on some steel, when I hear a pfft, I look over and see his pistol is not in battery and will not go into battery......and he is looking at it. Bangs on the back of the slide a sec, and I can tell I need to do something here.
Whats up.
don't know
Can I see
sure.
drop mag fish out halfway in halfway out unfired cartridge
lock slide back
Can't see anything funny, stick my finger into the back of the barrel....is something in there?
turn around look down its nose....no daylight.....you got a squib buddy, what ya shootin?
This, winchester white box. (he does not reload) and to him I define a brass goblin.
whats a squib
look down here, the bullet for some reason did not leave the barrel.
is that bad
ever see a semi truck hit a smart car
no
can you imagine it
yup
there ya go.
We shoot other stuff for the rest of the day, we get to the house and I say lets see that, can not, no way no how get that bullet out of the barrel...it is REALLY jammed in there....could it have been that oversized....no way.....all I know is it will not come out.
pistol apart, barrel out and a little more "force" is applied trying to get the bullet out. Well buddy I could get it out, and would get it out on my gun but don't want to do it to yours.....I really am into the gray area for my skill set here, might take it to a real gun smith.
you think you could get it.
sure
go for it
chance I could ruin the barrel
do you think you will
no, but there is a chance
ok do it.
sure
yup.
Ok.
Try locking barrel in a quick made up fixture and pushing it out with a long dowel rod and a wood working clamp that ratchets to put force on it.....busts the dowel rod.
Hmm.....one other idea is to drill it out.
can you do that
sure, lead is real soft I will know if I hit steel, but if I do hit steel it will not be good.
ok lets go.
(I am thinking at this point it has become something he is really wanting to see how I get it out)
Out come the drill bits, start small and work my way up.....REAL SLOW.
Finally we drill as much as I think we can without hitting the barrel itself, and a cut down dowel rod comes back into play.....crack. Well I have had about enough of this, get a brass cleaning rod and a 38 jag, it did come out, but the rod did not survive. Bore scope the barrel and all looks good....put together and on our way.
Now to swing this back on topic, we had lots of time to talk during this little project and we talked a great deal about gun safety, and you need to be in tune with just what that thing in your hand is doing, you need to watch for an impact after you shoot, any impact....something to show you that the bullet left the barrel.
I think having that happen to him was a bit of a come to Jesus moment, seeing first hand how stuck was stuck, me telling him....yea you are going to need to learn to wright right handed now (he is a lefty) as well as having a new nickname stubby.
After all this he asks after I retire am I going to open a gun smith store....hell no, I don't know anything, just enough to be dangerous. We go down the road on how he could never fix it, you have a different skill set then I do, nothing wrong with that and that does not mean you can't enjoy stuff. Loves his mustang but could not change the oil at gunpoint. Yea but you could rebuild the engine....yea perhaps in another life, but you know how, yea but you know how to do things I can't, you are a published wrighter, if you ever read something I wrote you would think a held back 3rd grader did it. (this guy also called a plumber to fix a running toilet) I am working on this.
BTW this guy is in his late 50's and married.
To swing back around to the topic again, he tells me if I do something stupid or miss something let him know, he wants to get better.....sure deal. We don't shoot side by side anymore, I do play a little more range officer now, but that is fine.
I can't tell you how to work into this subject with your friend OP, but you do need to try to have a talk with him
Dog that was long.