Reassurance can feel like an answer when what we’re actually looking for is relief.
“Do you think I made the right decision?”
“Are we okay?”
“Do you think they’re upset with me?”
“Are you sure?”

There’s nothing wrong with asking for another perspective.
Pay attention when the answer works for five minutes and then you need another one.

At that point, you may not be looking for more information.
You may be asking reassurance to give you certainty, confidence, approval, permission, or relief from not knowing.

The interesting question isn’t simply, “Why do I keep asking?”
It’s: What am I hoping the answer will give me that I can’t seem to hold onto?