I definitely think he tries to stay as mysterious as possible just because its so much easier to separate his work from the club with any personal life he may or may not have. Always wants to appear stoic and unaffected to the families more or less to keep anything he does have or had guarded. But at the same time, he would be the first to try to get everyone drinking and loosening up so he can collect information. So she's probably seen him at both extremes at some point I would think!