I think the system couldn't predict that a love interest with full memories and knowing the reason of the last loop wouldn't confront him, so the trigger to the penalty was avoided.
Boman didn't deserve this man, he's a dumb sack of bricks he didn't know he was doing wrong because he's a child. Like, a real child not an abomination like Ren.
I'm getting really bored with this manga's girl good boy bad, it isn't that hard to write actual antagonists instead of making Kane...