Flip flops, pillow or security blanket?

Jack is a fairly intense little dude. There are probably some good reasons for it, though. I've had him for 5 years but before that he lived through over 4 years of unstable and questionable living situations. Who knows what he went through before those puppy dog eyes lured me into taking him home?!

I suspect that, because of his uncertain past, he has some abandonment issues that have lingered during the past 5 years of relative stability with me. Inside his little doggy brain, I am sure he thinks, "Is she going to ditch me?"

I recently noticed that Jack has been laying on my shoes when I take them off. I've asked myself: does he just think they make for a comfortable pillow or is he thinking that as long as he is on my shoes it is unlikely that I will be able to leave without him?