Conversation Starters That Don't Suck

Conversation Starters That Don't Suck

Posted by : Alex Mills   /  

I can remember when I was dating my husband. We’d go out to dinner, swept up in the fun, carefree phase of the dating relationship.

I’d see people out to eat in much more “established” relationships. And I thought to myself… that will never be us. We’ll always have something to talk about.


If you are anything like me, you know that it’s frustratingly difficult to sit down with those you love, turn off the distractions, and actually enjoy a conversation over a meal that does more than graze the surface. It can be so hard to get through the first layer of “How was your day… fine” conversation.

And, if you’re anything like me, you also really desire that deeper connection. You get filled up by conversations that give you a window into the inner experiences of those you care about.

And, you may even feel frustrated at the lack the tools you have to tap into that.

We created a set of conversation starters - hang with me here, they’re not as cheesy as they sound. You’ve probably experienced cheesy, forced conversations built around prompts.

I know I bristle when I hear a cheesy question I’m supposed to answer for some sort of organized conversation. Talking isn’t supposed to be that way… it’s supposed to be organic and natural.

And it totally SHOULD be that way... Until you’ve reached that point in a familiar relationship when you feel like you’ve talked about literally everything there is to talk about and you’re left eating your food in silence.

So, we put together a little set of screen-shot-able or downloadable conversation starters that don’t suck. Some are designed to be insightful without being too deep for over-dinner chit-chat, and some funny without being cheesy.

And if it feels contrived to whip out your phone and read off a question to your dinner company, do a little bit of preparation for your time by picking one to start with and make a mental note of it. You can just pull it out again mentally when conversation lulls and no one knows quite what to say next.

We hope you enjoy!


P.S. If you use any of these, we’d love to hear about your experience. Drop us a PM here or an email at and let us know how it went.

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