10 (Really Deep) Conversation Starters for Anyone who Hates Small Talk

So, I have this problem when it comes to small talk – mainly that I tend to feel like I’m a floundering fish out of water every time I have to do it.

It’s funny because if I’m talking one-on-one with someone about strange, confusing, existential topics that I care about (strangers and friends alike) I am ALL ABOUT IT. That is my happy place. I’m into it. (My friends are all nodding their heads going, “Yup, sounds about right.”)

And even when it comes to speaking in front of other people; if I’m asked to talk about something that matters to me in front of a crowd, I’m also all about it.

BUT if there’s a situation where I’m expected to just casually chit chat about work or the weather with people I don’t know, or if there’s a situation where I’m (God forbid) required to…… MINGLE (I’m shuddering just thinking about it) that’s where we have an issue.

Now it’s not that I can’t do it, or that I absolutely hate it… I just… kind of hate it. No I’m kidding.

I’m exaggerating, but I would rather talk about the deep stuff.

Rest assured, I’m working on this. When I started my last job I didn’t set foot in the lunchroom for the first four months because I was so freaked out by all the small talk and mingling that I heard happening in there every day. (Lol true story). I share this knowing this is not something to brag about.

I also know that just because I’m a raging introvert (that undeniably has a little bit of social anxiety to work through), that doesn’t mean that small talk is bad or that I have an excuse to try and bypass it altogether.

Small talk is vital, in fact, because as great as deep conversations are, let’s be real here: not everyone likes being asked what they think will happen to them after they die before they’ve even been asked their first and last name.

So I’m working on it. Nevertheless, I do still love asking people hard questions, and over the past few months, I’ve compiled a list of my favorites (some from me, but most that I’ve borrowed from others).

So for anyone out there that’s about to embark on a long road trip with a close friend, or who likes to risk freaking strangers out by asking them obscure questions like I do, I hope you find these helpful:

1. What are you most excited about right now?

2. What question is really consuming you these days?

3. What do your inner voices/inner critics say to you?

4. What is the biggest mistake you’ve made, or way you’ve failed, that’s taught you the biggest lesson?

5. What do you like most about yourself?

6. What has been your greatest positive impact on the world so far?

7. What breaks your heart?

8. What do you want to be known for when you die?

9. Tell me one thing I don’t know about you, or the world.

10. What is the best piece of advice you’ve ever gotten?

Thanks to Jonathan Fields, Liz Gilbert, John Maxwell, Lewis Howes, et al for (unknowingly) contributing to this list.

Happy Conversing!

E