well
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».
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.
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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...».
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.)
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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...».
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.