1 Well is often used at the beginning of an utterance where the speaker wishes to inject their personal opinion or reaction to or feelings about something they just said or heard; to sum up the speaker's or someone else's impression of the last thing mentioned. It tells the listener «Having said that, I'm going to tell you how I feel about it».

In this example from 001, I mention what Samantha asked me to do for her, then I use well to tell you, the listener, what my reaction was; how I felt about it. In the second example, also from 001, we have well twice. First I react to Samantha's request, then I react to what I figured she was thinking when she asked it. In both cases, I'm sharing my feelings/reactions.Note that in this usage, well is pronounced in a neutral tone and usually very closely followed by the next word, but not necessarily. For example, in this story, I say Well ͜  I was livid with no pause. However, in the same story, I say Well, nice is nice with a pause after well

Anyway, she told me that she had already hired a dog-walker to walk them in the morning and in the evening, but it would be great if I could just go into her apartment before bed and check in on them, so they wouldn't feel all alone. Well, I figured it'd be no trouble peeking in and saying goodnight to Nacho and Flor, so I said ok. I figured as long as I didn't have to touch them, let alone walk them, it was no biggie.


So that night, I get a text from Samantha: "Hey, my dog-walker just bailed on me last minute. You think you can help me out?" Well, I was livid. It was so obvious that she had actually fired the dog-walker because she figured I was willing to do everything for free. Well, nice is nice, but this was too much. So I told her I was sorry, but I thought she should just go ahead and hire a new dog-walker.

2 Sometimes well is used to preface something you simply can't say any other way... usually something which may be offensive or negative, or simply something so obvious that you can't make it any plainer. In this usage, it has a nuance of «I can't think of any other way to say this...».

We have an example of this in the first paragraph of 001 Nacho and Flor, where I thought the name Flor was silly because it sounds like the English word floor. Since Flor and floor sound exactly the same, I hesitated for a moment because there was really not much more to say — the two words, side by side, speak for themselves.We see it again in the explanation of the snippet in Discourse Markers > This about the woman with the tattoos. Here, we're already talking about stories, and there's no better word to use to describe this usage of this than a story. I hesitate to use the word story again because it's a bit redundant, so I use well for this "hesitation."In this context, well is pronounced in a hesitant tone and followed by a significant pause.

So there's this woman on my floor, Samantha, who has two chihuahuas, Nacho and Flor (...which is cute in Spanish because it means flower, but in English, it just sounds like, well... floor.)


Similarly, this one tattoo points to one specific tattoo of the many the woman had. Here, the speaker is marking every significant element of the story with this/these. This may sound excessive to you, but to the American ear, it just sounds like, well... a story.

3 Sometimes in life, we make what we consider to be the perfect plan and then something or someone comes along and "throws a wrench in the works." This can be a force of nature like a storm or a natural disaster, or something unforeseeable like an accident, or someone does something to ruin our plan or simply replaces it with another one. Whatever the cause, when we want to express that there was an impediment or that the opposite of our plan took place, we often use well to express our disappointment.

Here, intonation is key. This well is short and low and usually followed by a brief pause for dramatic, sarcastic, cynical effect

In this usage, well has a nuance of «That would be/have been great, but...». 

In this snippet from 006 Staying Alive, I describe the plans I made to surprise my family by showing up in Florida on my birthday without them knowing. After laying out my plans and explaining how this was going to work, I suddenly say: Well... But it's not so much that I say well, it's how I say it. Listen to the recording and not the intonation, the length, and the pause that follows. All these factors contribute to the effect. This short well already lets you know that things didn't go as planned, and let you know that I'm about to tell you why.

The idea was to surprise my family. In other words, they had no idea I was coming. I reserved a room in a luxury hotel on the island of Palm Beach and booked a flight. My plan was to have my aunt in Florida invite my family to dinner at the hotel, and then I'd show up and surprise them. Well, we have a saying in English: “Man proposes and God disposes.” That means that sometimes in life, we make plans, but then our life takes a different course altogether, as if ignoring our plans and obeying another voice — a higher authority.