This one sounds a little bit weird because it evokes some of your bad memories from the past. I mean, no one likes to remind themselves of their previous, crappy job (unless someone insists on it).
But, believe it or not, his intention is not to remind you of your crappy job but to sympathize with you.
If he’s asking you to share some painful experiences from the past, his only intention is to bond and connect with you. We, women, do it in a different way, and that is why it’s hard to understand.
And guys think this is a perfect way to show a girl that they want to connect with her and that they understand her.