No, he'll know it's something distressing for her, and explain it properly but maybe whimper about how cute she is jealous and how she should punish him just for being away and how she's welcomed to go crazy and drag him away from others when she wants
SPOILERSSSSS
trust me he did in the novel, he did make her misunderstood on purpose, he said that that girl was his fiancee so Courtney overthinks, what if he got bored of her and he's gonna make that girl his new master? What he didn't tell Courtney is their engagement was way long in the past, back when they where kids or teens. Their engagement did not last long, i think, i can't remember. I don't know if they gonna change what happened in this manhwa but that was what happened in the novel.
since richard is a sucker for punishment, he'll deliberately make Courtney misunderstood his words and make her jealous
Richard, the whore you are ┐( ˘_˘)┌