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E string too thick to fit through hole in bridge.

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While this was probably a joke :) it's actually not a bad idea to put something on the end of the string.

I think my personal solution to this would be Light, slow, careful reaming - just a few strokes - along with some sort of lube on the end of that string - either a graphite type lube, or maybe even a coupla squirts of WD40.
If WD40 gets into any wood it will swell, in this case making the hole smaller.
Other than concern over making the hole too big for strings with no silk wrap, I’d be inclined to open the hole a little.
 
Wow guys! I appreciate the responses. Thank you all!

It's a used bass ( in near mint condition) that I got from a guy on CL selling off his brother's collection. His brother was moved into an assisted living facility and the guy priced it low so he didn't have to haggle. I got it for $150 so I'm not too concerned about the bridge or the cosmetics of it. I will take the advice of using a hand drill rather than an electric one if I go that route.

However, I'm going to try the 'less invasive' suggestions before resorting to drilling. First the beeswax and if that does work then cutting away some of the silk and dabbing the ends with crazy glue to prevent it from unraveling.

I'm going to fix it this afternoon and I'll keep yas posted. Thanks again. ;)
 
IMG_20200703_194116.jpg
Here she is. Thanks again fellas. I'm going to fix that that tomorrow.
 
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It seems if anymore of the string goes through the hole, then the tapered, winding near the ball will be sitting on the saddle?
This could be true but maybe not. Once the hole is slightly widened and the nylon does go over the bridge as you foresee just add a few small washers to the ball end. What brand of strings were on it before this string change.
I'd just make sure the ball end of the string is truly round, no bumps or thickness areas then invest in a cheap Rat Tail File. Same as a regular flat file but round and it tapers smaller at the tip. Start filing from behind the bridge to the front. May only take a few passes with the file.
OR, buy different strings and check that the ball ends are suitable. It may be easier to just get a lighter gauge set and turn up your amp a bit to compensate. IDK but before I'd start modifying my bass I'd think about the fact it's worth a lot more than an errant, machine wound, set of strings.
Rat Tail File
Rat tail file.jpg
 
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Point taken, Dtripoli. I proceeded with caution and used a hand drill. I went slowly, drilling a little then trying to pull the string through multiple times. It was a last resort type deal but your rat tail file is a great idea! I might use one on the g -string hole.

The strings don't look like tapewounds in the second photo I posted (just noticed). They're so polished and silky that they reflected the grey clapboard of the side of my house. I love the tapes! When I bought the guitar it had bronze strings. I know they were D'Addario's from the color of the ball ends.
 
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