Yeahh no the chairman is too much of an immature asshole. "The very sight of you pisses me off" was overkill, I understand he's a nepo baby but he could at least TRY to communicate more constructively towards a subordinate.
The dead wife looming over Appliance Guy's psyche isn't ideal, but neither is a potential partner who comes with an acerbic old fart as a package deal. I would've been content just to see the two of them work through their relationship without a love triangle being thrown into the mix.