In what context would you consider this an IoI, or maybe a self-esteem issue?

This has happened to me on a number of occasions and I'm not certain of how I should interpret it.

Examples:

Over text: "I'm not that popular, so figuring out a time to do something is never complicated".

In person: "You can only have 4 in your group, so you're gonna have to kick out your friend to make space for me" "Well, we are trading up. Katy will understand."

Thoughts?