Okay, I thought: "So, why not?" I've got a feeling that Bar Lady is going to have some coming screen time so I think that what happens next with Clinton. I know a few of those options look silly; option 4, for example extending from the suggestion made that Bar Lady may be Sam's mother.
Personally, I voted option 8. I've just got a feeling that he just needs someone to verbally slap him upside his head. The date with Emily shows that he can be unexpectedly spontaneous under the right circumstances. Who knows just how he may take her attempt to get him to stop telling her his troubles? "Do something instead of bitch about it!" for example could have an unpredictable outcome!
BTW, Wednesday is Star Wars day!