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