Is this dipstick supposed to look like this?

[Pterostylis]

Got a link?

They’re not coming up now.
This morning I just did a Google image search for “dodge Dakota 3.9 plastic tipped dipstick -tube” and about 30 images down it showed one, which when expanded showed a few others. They were black T-handles with a black tip but it was a bit smaller than the one you showed.
The only one I can currently find is an aftermarket one with a red “precision” tip but it’s not for a Dakota.

 

[53' Stude]

It's made that way. Normal. It helps guide the stick into the tube

That’s a new one. I have vision disease and even I can put a dipstick into a tube.

 

[JHZR2]

Mercedes dipsticks have had plastic ends for 40+ years.

 

[paulo57509]

Easier insertion and removal, and prevents "oil cling" for more accurate readings. TBH, how accurate does the reading need to be?

In this case, the OP needs to add a few quarts.