"Oh a harem, that must have been fun." It's the quickest assumption to be made if she was 'collecting' people. Hawke isn't going to jump right to the worst possibility, although he is certainly keeping an eye out for it. People used to tease him about having one too, with his unsavory gang of (very pretty) misfits. Luckily he's used to being without them now, otherwise he'd be missing them.

"Ah if only my friend Varric was here, he wrote an entire book about our exploits, although only about half of it is true." It wouldn't do to admit to things that would get them the wrong type of attention, plus Varric likes artistic license. Hawke heard later about the tale he told Cassandra when she was looking for him, it was quite amusing how much he left out. Must've driven her insane.

"Well I'm a dead man anyway, pour away if you'd like." He winks at her. "Although you might want to ask yourself if I'm skillful enough to poison someone underneath their nose. You never know with strangers." Hawke cannot in fact do that, nor has poison ever been his way, but he literally has assassin friends who could do it without anyone knowing.