Awkward conversations: how to start and finish them in style

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Awkward conversations: how to start and finish them in style

Awkward conversations are difficult. They don’t have to be. Here are seven tips on how to start an awkward conversation and finish it.

If you Google “how to start an awkward conversation,” you’ll find that the search results come up with something along the lines of:

Did you mean, “How to avoid having awkward conversations”?

Most of the time, we want an easy life, free of conflict, and uncomfortable moments in coffee shops. But sometimes, awkward conversations are the only way forward. Whether it’s addressing a health issue that is impacting you or something that is impacting a friend, it can be really difficult to know how to start, structure, and end awkward conversations.

Awkward conversations are a two-way street, so there’s no way for us to plan or predict them from head to toe. But what we can do, if we are going to plan to have a difficult conversation, is look at the variables, and assess how we can avoid the pitfalls and adopt some killer-convo strategies.

Got it? Here are our 7 tips on how to start an awkward conversation

1. Keep the conversation short

Start off the awkward conversation by explaining what it is you want to tell them (prepare this), but don’t ramble. Be concise, and clear about what the issue is, how you feel about it, and what you’d like to achieve by having this conversation. Then, let them speak.

2. Listen actively to what they have to say

You already know what you want to say. But do you really know what the other person wants to say? You do not know for definite how the other person is feeling, or what new things they may bring to light in the conversation. That said, it’s easy for your mind to wander off into its own little self-indulgent forest of thoughts and feelings, so the best way to make sure that you’re actively listening is to repeat back what you’re hearing. I will say that again, repeat back what you’re hearing.

“I can see you feel strongly about this, and I didn’t realize it was affecting your health also.”

“I now understand what you mean about the party, I may have been upset when you arrived, but I didn’t realize you had been left to deal with Aunt Marjorie on your own.”

In doing this, you’re forcing your own brain to engage with this new information, and you’re also communicating to them that this isn’t just about you; you are actually looking for a joint solution.

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4. Don’t say things you don’t mean just to fill the silence

Very important. My counselor taught me this one when I sought their advice on how to have difficult conversations at work or at home.

When I’m trying to have an awkward conversation with a loved one, I often find myself reeling off meaningless phrases, or worse, niceties that completely contradict the very thing I was trying to communicate:

“Look, don’t worry about it.”

“It’s fine.”

“I know what you mean.”

These are CLASSICS that can fall out of your mouth before you’ve even realized it. No, it’s not fine. No, I do not know what you mean (unless you do actually know what they mean, then you can say that). That’s why we’re here talking about it.

A group of young adults are sitting on a lawn having a successful awkward conversation

Being able to empathise with another person's point of view, being able to acknowledge that there is another living-breathing-entity sitting in front of you, and that that living-breathing-entity is experiencing the world in a way that is different to you, is the key to having healthy, meaningful, loving relationships.


©Viacheslav Iakobchuk / Adobe Stock.


5. Experience the silence

This will be hard, and you will feel the urge to just say anything, anything at all, about the color of the floor, or a speck of dust on your fingernail, but bite your tongue. It’s not comfortable, but neither is what’s lead you to have this awkward conversation. Don’t hijack the silences; let them exist as an opportunity for you both to think, and process the new information being shared.

Read more: Why are difficult conversations important?

6. Beware of mirror neurons

Science. In the race to be crowned World’s Most Stupid Anatomical Feature, mirror neurons come in at a close second to the amygdala. This is your body’s instinctive reaction to the signals being given off by the humans around you. It’s why when someone starts screaming in a mall, it won’t be long before someone else starts screaming. Even when the second screamer has been presented with no evidence to justify the reaction, they mirror it.

Beware of mirror neurons getting their claws into your conversation. If your interlocutor is getting angry, or overly emotional, try to remain centered, and focused on what you intend to achieve here. Being aware of mirror neurons will make you less susceptible to the phenomena, but if you need another distraction, either take a deep breath, go for a quick loo break, or do what I do, and think of something that makes you smile and takes you out of the situation for a split second. Here’s one for free.

7. Empathy is key: bring your best namaste

Empathy is, in our opinion, the single most valuable quality that a person can possess, and absolutely key to having a productive conversation. Being able to empathize with another person’s point of view, being able to acknowledge that there is another living-breathing-entity sitting in front of you and that that living-breathing-entity is experiencing the world in a way that is different to you, is the key to having healthy, meaningful, loving relationships.

You may not always fully understand, or approve of, the choices and behaviors of others, but using your own emotional intelligence to put yourself in their shoes, even just for a moment, and at least trying to conceive of what has led them to those decisions, is half the battle.

Final thoughts on how to start awkward conversations and finish them

Remember, to start an awkward conversation keep it positive and relevant, stick to “I statements” to express how you feel without playing the blame game, and be open: you never know what unexpected progress you may end up making.

Lastly, if the conversation does end up being a mess from beginning to end, don’t be too hard on yourself. It takes a lot of guts to broach difficult issues with the ones you love, so take heart. Every awkward conversation you have, no matter how successful or disastrous, will teach you something new about how to do it better next time, which can only be a good thing.

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UR is on a mission to change the way we talk about sensitive health topics, one awkward blogpost at a time. Posts by this author are from the Editors at UR.


You're going to have to have an awkward conversation at some point, so you might as well jump right in.