Owen was pretending to tie his shoes at a short distance from the conversing pair. He heard Lucy say yes to Jimmy's invitation to the drinking party. He does not feel comfortable with Lucy going out drinking alcohol with a bunch of guys even if he would also be there. He was ready to interrupt before he remembered how Lucy acted earlier about him going out for drinks.
"You can go out. I trust your judgment."
Lucy made it clear to Owen that she trusted the man enough to trust his decisions on personal engagements. Owen was guilty about not having the same amount of trust towards the woman but he realized the mistake immediately and pulled back. He finished tying his tied shoe and got up to go to the massage room without greeting Lucy or Jimmy who were not in his direct periphery.