What's something about you that you find difficult to deal with?
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I can be insufferably insistent at times. If someone says they'll do X with me, or for me, I will pester them until they do, "playfully" jabbing at them the longer they don't do whatever they said.
Honestly doesn't sound too bad. If I had a friend who both reached out, and then pestered me, I might actually feel valued lol