How to Deal with Awkward Online Conversations

How to Deal with Awkward Online Conversations

How to Deal with Awkward Online Conversations

There’s always that one person who has to step in and ruin a perfectly good conversation by saying something awkward. You know the one: you send out a perfect tweet that you’ve thought about a LOT, and they criticize it for no reason. Now, this is a bit different than a troll, so banishing them from your kingdom by throwing them back under a bridge might not be the best option.

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Sometimes when you’re chatting online, you might not know if someone is joking or not. Does that happen to you? It happens to me in real life, too, but that’s a whole other story. Using an emoji can signal to the other person that you are indeed joking. Or that you’re angry. Or happy! Here’s a fascinating article: 7 Reasons to Use Emoticons in Your Writing and Social Media, According to Science.

By the way, did you know that Twitter measures the sentiment of your tweets using data science? You can search for a word, then go to Advanced Search and scroll to the bottom. So, for instance, you could search on Startups==>>Advanced Search==>>scroll to the bottom and check the positive emotion box. And voilà! You’ll have a list of positive tweets about startups.

Silence is Golden

If you feel that a conversation is veering into an Ocean of Awkward, one of your best weapons is silence. Like the space between notes in music, silence has power and isn’t used nearly often enough. So if there’s an awkward question, let your weapon of silence loose! Also, if you’re an introvert (like I am), silence can drive the extroverts in the room absolutely batty. So there’s that. Here’s an article about introversion that I enjoyed writing: Six Facts About Introverts and Social Media That Will Impress Your Friends.

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Forgetting Names

Online, people have aliases, avatars, and bizarre names. And yet they expect you to remember their names without having an accurate name tag! What’s a forgetful person to do? You could ask a friend of your friend. If you haven’t known your new friend for very long, you could ask them directly, too.


If someone’s friend has passed away, what do you say? It depends. If you don’t know them too well, you can say you’re sorry for their loss. This works as a good first step in any case. And if you don’t think that the Internet Has Changed the Way we Deal with Death, then you’re mistaken. We grieve online as much as online now. Think about when your friends of friends have passed away. And think about Prince passed. What a huge outpouring of grief online! Other ways of dealing could be sending cards, private messages, cards in real life, real flowers, gift cards, and so on.

Feeling Awkward?

Has this entire post made you feel even more awkward than you already feel? Leave me an awkward comment! Then we’ll both feel awkward. But at least we won’t feel as lonely.



  1. Names.

    Names are the toughest because they are usually screennames. And still, if you’ve only read the name, you’ve never heard it pronounced. And it’s hard to keep them all in your head.

    Good tips.

    • Right, Bridget? So if you’ve only seen a name online it’s part of your reading vocabulary! I’ve thought of writing them all down somewhere, but where?


    • Hi Bridget:

      This doesn’t always work, but if someone has a weird name, I will try to find podcast appearances, YouTube videos, some type of audio with someone saying their name. This option isn’t always available, and the reference may not always be correct either! So I try to watch for that with odd names.

      • Hi John,

        That’s funny and a little awkward that you’re replying to Bridget here. Good one! Hahaha!

        Good idea about looking at a podcast, video, or audio of the person’s name.

        I hope you don’t mind being teased, a little.


  2. You want an awkward comment?

    Erm… Ok…

    Actually, can I get back to you on that?

  3. Excellent post! Thanks for the suggestions. I had a weird reply just last night on Twitter. I had tweeted about a news article and this person I don’t even know told me I was part of the problem and then started talking about click bait. I paused for a moment and then I replied did you read the article? I have not heard from them since.

    You provided really great advice. Here’s a link to a TEDx Talk that I think could be useful for the grieving advice.

    Thanks Carol for the good advice!

    • Hi Justine,
      That Twitter conversation does sound weird! My goodness, sounds like someone has an anger management problem that’s leaking out onto random people. Glad you got out of it, Justine.

      Thank you for the TED Talk link, too.


  4. Some great advice Carol!

    When I get awkward comments I try to access the reaction they’re after. Some want to create trouble or start an argument. Others simply want you to follow their links or get some visibility off you’re content.

    I thank them for the comment and move on. If they ask a direct question I’ll answer it. I’m not afraid of the conversation. The trick (and I have been guility too) is knowing when to stop and avoid the rabbit hole.

    The most awkward for me are the posts about someone dying. Most of the canned responses come off as just that to me. As with birthdays, I prefer to message people privately to help both avoid the ‘awkward’ comments.

    • Hi Robert,

      Yes, avoiding the rabbit hole can get tricky. Sometimes it’s hard to know what someone’s motivation really is, so we just have to give it our best guess.

      Anyone being sick, or a death in the family are the hardest conversations for me as well. But cliches exist for a reason, I suppose. I’d rather err on the side of a canned response than not say anything.

      Thank you for stopping by!


  5. Sammy Blackmore says

    Awkward online conversation. When I messaged someone on Twitter about a particular subject, and a bot will reply promoting me with something without answering my inquiry at all.

  6. This is GREAT article, Carol (which is why I re-tweeted it!) and I don’t feel awkward after reading it.
    You always fire me up!

    I have a feeling I’ll return to this post again for a refresher because I’m not interactive enough on Twitter. Hence, there aren’t many opportunities for awkwardness to even enter the picture – does that make sense? I think it’s a sign of one’s social media success to have this problem! Uh, I mean….
    challenge! :))))

    I’m also an introvert, so I need to read the 6 Facts about Introverts and Social Media now, don’t I? ;)

    • Hi Dyane,

      Thank you so much. Flattery will get you everywhere! Hahaha.

      You seem very interactive on Twitter, Dyane. It’s hard to tell who’s an introvert and who’s not online, isn’t it? I wouldn’t have pegged you for an introvert. Anyway, us introverts need to stick together!


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