Okay, so the theme of the night seems to be romantic frustration. Or confusion, at the very least. And since our beloved Whiskey isn't here to crack out the manual, here is your emergency romance hotline (hot thread?).
IMPORTANT CAVEAT: This has to be a group effort. For the love of God, this has to be a group effort. I am terrible at this sort of thing and emotionally undeveloped to the point of middle school-dom. While sometimes that means I can give practical, unemotional advice, mostly it means that I am not qualified to help with this kind of thing at all. So let's all help each other, folks!
ETA: Y'all are wonderful! Thank you for helping each other out while I went to go eat my late, Mountain Time dinner.