Did you (or the previous owner) forget to install the lower guide dipstick tube into the block?? It goes into the block dipstick tube location before the upper tube is inserted. Its function is to guide the stick down into the pan past the crank and main cap. If it isn't there the dipstick will try to curl either up towards the crank or down and out towards the pan side.
Commonly lost or left out part at rebuild, it is basically just a piece of 5/16" fuel line about 7" long with the flare still on the upper end to keep it from falling through into the pan. The factory piece is slightly larger than 5/16" to fit tighter in the hole, but 5/16" works fine, the upper tube holds it down and tight.