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I had an incident yesterday where it was late at night and an acquaintance/friend called me to come over to help him with a non-emergency urgent matter, so I told him I would love to help him, but it's really late and I really need to get to sleep, but he refused to accept that and continued pleading with me to come help him. It got to the point where I just hung up on him.

I feel really bad about doing that, but I didn't feel like I had any other choice. Is there anything I could have done to end that conversation properly and perhaps even on a friendly note?

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He probably knew you would feel bad, and that's why he did it. He was taking advantage of your feelings in order to get his way at your expense.

If it's true that he will just keep you on the line at your expense, then there is no way that the conversation will end with him satisfied.

Be polite; be firm; and be on your way to getting some sleep. Before doing this, if it's OK with you, invite him to make an appointment when it's convenient for both of you. His refusal to do this should go a long way toward confirming his rudeness (and allowing you to not feel bad about it hopefully).

Simply conclude the conversation by saying something like the following (without pausing if he tries to interrupt):

It's been nice talking to you. I'm going to sleep now. Good night.

One might say it's a technicality. But I would say the above is not completely hanging up. It's concluding a conversation on your terms while you are speaking. (Hanging up in a completely rude way would be if you hung up while he was speaking.)

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  • I agree that saying something rather than just hanging up comes off as more polite and more socially competent.
    – Casebash
    Commented Jul 18, 2017 at 0:53
  • Can you back up your initial assertion?
    – HDE 226868
    Commented Jul 18, 2017 at 1:27
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    @HDE226868 I cannot, and that is why I used the word probably. But I will say I am hard pressed to think of a more likely reason. The last time this tactic was used on me, I was listening to a sales pitch. The salesman refused to hang up until I either paid money or hung up on him. He was banking on the chance that I would not match his rudeness. He was wrong but I did it as politely as I could -- as I stated in my answer.
    – John ♦
    Commented Jul 18, 2017 at 4:22
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Before hanging up, I would try saying no in a very clear manner:

"[NAME], I'm really sorry but I cannot help you"

You start with their name in order to get their attention. You say that you're sorry as to be more polite. You explicitly say no ("I cannot help you") rather than implicitly saying no ("it's late") so that the message is clear.

This is particularly important when someone is distressed and they may miss these signals.

If that doesn't work, I'd go with a slightly modified version of John's suggestion:

"I'm really sorry [NAME], but I've got a long day tomorrow and I need to go. I hope you find someone to help you. Good night!"

The main difference between my suggestions and John's is that you are suggesting that because it is late you have to go to sleep, while it John's it may be understood as you choosing to go to sleep as you haven't offered an excuse as to why you must do it. The person you are speaking to might infer that you are choosing to go to sleep to avoid having to speak to them.

That said, the best response also depends on your relationship with the other person and how honest you can be with them. I can imagine situations where it would be best to say,

"[NAME], I'm going to sleep"

Which would clearly indicate that they are annoying you to some degree. With the right person though, they will accept that they were being annoying and respect you for setting boundaries.

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