Why, yes! You would be able to roll for it in one of my games!
Speaking of... I'm looking to run a oneshot this weekend. A quick 3-4 hour adventure. I've run it before and everythings prepared, just gotta find the players for it! So if you're available to start a session between 5-8PM EST on Saturday or 1-8PM EST on Sunday, then check out my thread below!
Let's say you want to haggle a better price at a shop.
You can start by explaining that to your DM.
They might ask how, and you can just generally describe what you'd like to do.
Not sure how to explain? Ask the DM to better describe the shop or individual.
Then pick something, maybe they have a sweet hat, or a cool earring. Maybe the store looks really clean or maybe all the other patrons are dressed fancy. Maybe you can investigate the craftsmanship of the weapon or shield and compliment the shop owner.
The important thing is you pick something, it doesn't matter what. Maybe that earring you commented on is a family heirloom. Roll well and the shopkeep is reminded of their family an gives you the family and friends discount. Roll poorly and the shopkeep is reminded of how their family was brutally murdered and they ask you to leave.