I have had a thought about learning to use the thimble - it's how I learned to use one.
Back many many years ago when I was in the Army I had a need to sew patches on my shirts. I had a small sewing kit which contained a cheap plastic thimble. After almost bleading on my new shirt and patches, I finally got out the thimble.......it solved my problem. Sometime we have to be forced to do something to learn how to do it.

I used to use the leather & elastic thimbles but found they didn't last long enough. I started using the metal "cheaper" type (lip around top to keep needle from slipping off) & keep a few different sizes for when the hands are cold or whatever. It's like all new things, practice using them alot & pretty soon, you wonder how you did without them.

No matter how many thimble's I've tried I keep going back to the old timey one my mom used.

I have tried almost all kinds and really never liked them because they were so hard to fit my large fingers. : So I bought a $90 sterling silver one that was supposed to work great but didn't. Also have plastic ones, metal ones, and leather ones but found the silicone with the metal tip that EasyPeezy is talking about and it works great! The silicone seems to just self-form around my finger and is not stiff or wobbly. You just have to find what works for you...

I bought my thimble too big and put a ban aid on the inside fits perfect now.

This is my favorite as well. They come in sm, med, and lg, so they fit a big range of fingers, lol. They cost about 9 bucks, but last a long time, if your puppy doesn't chew them up. ha ha.

A hint that a fellow member of my guild told me was to blow into your thimble before you put it on, and it won't slip off.

I have tried a number of different ones; the silicone ones feel the best. I got "used" to using one by wearing it for several hours a day while doing whatever.

For hand quilting I have used Roxanne's and Thimblelady's thimbles and liked them quite well. I recently bought a T.J.Lane which isn't as bulky as the Roxanne and Thimblelady. I bought one for my finger and my thumb. I need a silver thimble because of skin allergies. All of these thimbles allow you to push the needle with the pad of your finger rather than the end. Having said all that, a thimble is a personal choice. For hand quilting, I recommend finding a thimble that is comfortable to wear. If you quilt with the rocking stitch, make sure it has deep dimples to hold your needle. Try the thimble on and shake your hand. If it doesn't come off, it's a good fit. I must warn you that our hands change sizes from day to day. If your thimble becomes loose, just dampen your finger (I just lick mine) and it will fit. If it's tight, I just wear it until it eventually fits again. I wash mine with soap and water periodically to get rid of the body oils that causes it to slip.

I do not use the same thimble for quilting and sewing. I use a traditional thimble with a flat end for sewing, embroidery, etc. I don't remember the brand, but I've had it for years and take great care to not lose it.

If you have no allergies, start with an inexpensive thimble. When you find a style you like you can upgrade later if you choose. If the metal thimbles you have tried on are too tight, you just haven't found the proper size.

Fit is so important with a thimble. I took a class from a lady who quilted with two thimbles - one on the top hand and one underneath - it was a painless way to hand quilt!