Glad I could be helpful! :)

I'm totally on board with the idea that empathy is a skill that you hone, not necessarily some in-borne character trait or ability. Sure, some people are probably naturally more empathetic than others, but being good at empathy takes work and practice and it's a skill we should all learn.

Empathy through rational, logical thought processes is totally possible. What it requires is a very specific kind of approach, and an understanding that the #1 authority on how or why a person is feeling a particular way is that person themselves, and that feelings are not right or wrong in and of themselves, they just EXIST and need to be dealt with accordingly. (In other words, you can't make a feeling go away just by providing a solution to what you think a problem is, or by fully parsing out why the emotion exists.)

Here's what you do:

1) LISTEN. If a person is telling you that they feel a certain way, don't argue with them. If they're explaining why they feel that way, even if it seems illogical, even if you don't understand, take that information in.

2) VALIDATE THE EMOTION. You don't have to agree with the logical thought process to offer comfort. You can be genuinely sad that someone feels bad. Saying "Wow, I'm sorry you're going through that," or "Man, it sounds like that really sucks," can go a LONG way. (Remember that if someone is confiding in you and NOT specifically asking for advice, giving advice is actually solving the wrong problem. The problem is the emotion and talking about it and being validated is often what the person needs, rather than to have someone try to fix the thing that caused the emotion in the first place.)

3) TAKE IT IN. Now that you've heard someone explain what they're feeling and why, you have more information with which to try to parse future situations with. "Experiencing X made this person feel Y." Even if you wouldn't feel that way if X happened to you, you know that at least ONE person felt that way. Observe other people. Do a lot of people tend to feel Y, or similar emotion Z, when X happens to them? Even if you wouldn't feel that way, you can recognize that it's a common emotion and add that to your data bank.

4) RESEARCH. So, I'm not saying that you should necessarily google "Why would someone feel Y when X happens?" (though that may not be the WORST idea if you're at a loss). But being aware of why human beings act the way they act, what common reactions are to specific scenarios, and maybe even the scientific reasons behind some of those things - that can help you extrapolate to future situations also.

Every time you repeat this, you get a little closer to rational empathy. The more experience you have with people and the myriad reactions they can have to myriad emotional situations, the better you'll be able to extrapolate common reactions and emotions, and the better chance you'll have of understanding the connection between X and Y or even Z.

MBMBAM is not my favorite, but I do enjoy RPG stuff, so I may have to check this out!

I have fallen out of podcasts a little bit, but recently Dear Sugar Radio pulled me back in! I'm a bit of an advice column junkie, and Dear Sugar was one of my all time favs. Now Cheryl Strayed (the famous Sugar and author of Wild) and Steve Almond (the original Sugar) have teamed up to start a podcast. It deals with pretty intense emotional stuff but if you like advice columns or learning pretty valuable life wisdom from people who have lived fascinating and storied lives, give it a try.

If you're a history buff, or not a history buff but mildly interested in ancient roman history like me, The History of Rome is pretty awesome. There are a ton of episodes - it's a pretty thorough history - but well told. Same guy started a Revolutions podcast after he was done with Rome, I still need to check that one out.

Savage Love is one I haven't listened to recently, and Dan Savage isn't perfect, but it's also great for advice about anything sex-related, and definitely helped me change my perceptions about a great many things.

My husband loves his podcasts, and here's a few he listens to:
-My Brother, My Brother And Me - also advice, but kind of comedy advice? They often take their questions from Yahoo Answers, which gets pretty funny
-Giant Bombcast - podcast from the video game website Giant Bomb. Great stuff if you're interested in video games
-Comedy Button - uh, comedy stuff?
-Sawbones - Husband and wife podcast about bizzare, disturbing, and often hilarious medical history stuff

My husband and I had that conversation within the first few years of us dating. It was definitely beneficial for us. I can imagine a lot of people becoming very uncomfortable at even the thought of a conversation like that - but maybe that's a sign that it's a conversation that needs to be had. Definitely food for thought.

I think when someone is just awkward because they're nervous about making a good impression, it can be cute. But if they also acknowledge the awkwardness and move on like it's normal, it makes me go "oh yeah I'm awkward too sometimes" and then I feel more connected to them because it humanizes the other person.

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Edit because I had some seriously awkward spelling of the word awkward ;)

Sometimes I find, too, that being able and willing to both a) get ahead of the awkwardness by acknowledging it, and b) treat it like no big deal is a great way to move past a moment that is genuinely awkward and visibly so to others.

So, imagine you are having a conversation with someone - say you fumble with your cup and almost spill your drink while the two of you are talking - and it's clear from the way the other person looked at your cup that they noticed. Perfect opportunity to go "Whoa" and then laugh and then "That could have been a disaster!" or "man I'm so clumsy! haha" and then "Anyway..." and continue on with the conversation like nothing happened.

This is sort of umbrella-ed under letting yourself be imperfect, I think. Just make sure not to turn it into a situation where you're going "Man, was that awkward? I bet that was awkward. Let's focus on how awkward that was."

Yeah, Chasing Amy is a wonderful example of how NOT to handle this situation! (And also an excellent movie.)

"She's just as much a dirt bag as past Doc was (sorry Doc; again, I understand you are a different person now) for engaging in such activity while in a relationship."

I'm not sure I agree with this, because we don't know the terms or context of her relationship. She obviously wasn't in an open relationship, because it seems clear that she was interested and it was the relationship that was stopping her. On the other hand, the lines of what is acceptable behavior while in a relationship differ from relationship to relationship. Some people really enjoy having their significant others tease other people and bring that energy back to the relationship with them. It is entirely possible that Jay's behavior was on the up and up.

Yeah, I agree with your #1. If I go to a coffee shop or a restaurant or an eatery alone, I always bring a book or something just to have something to do, but that doesn't always mean that I'm not ok with being approached (sometimes just the opposite - I'd be glad for the conversation and the book is just the backup option!). I think your advice is perfect - if the person is glancing up a lot, making eye contact, smiling, etc, then an approach is probably ok.

But either way, if you approach and get a one-word response and she looks back down at her book? Best reaction is probably this one.