5 Tips for Starting Real Conversations on Instagram

Krys Benyamein shares five actionable tips for starting real conversations on Instagram, from leveraging DMs to engaging with Stories. Perfect for building authentic connections online without the awkwardness!
5 Tips for Starting Real Conversations on Instagram
5 Tips for Starting Real Conversations on Instagram
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FREE VIRTUAL EVENT
BAM BBQ 2026

If you're still treating AI like a search engine, this is for you. BAM BBQ is two and a half hours of real instruction on AI for real estate, from conversations to content to systems. It’s free, virtual, and loaded with plays you can run the same week. Save your spot →

Have you ever hesitated to start a conversation with someone you know on social media? That tricky in-between space where you want to connect but aren’t quite sure how to break the ice?

If that sounds familiar, you’re not alone. Over time, I’ve discovered strategies that work incredibly well for initiating meaningful conversations online. 

Here are five practical tips to help you start new conversations with new people online—without feeling forced or awkward.

#1: Send a DM 

Direct messages (DMs) are one of the simplest and most effective ways to connect. When someone new follows you, don’t let the moment pass by. Reach out!

I have two go-to DM scripts: one for real estate agents and another for non-real estate professionals. These messages are tailored, making them feel genuine and relevant to the recipient.

If you’re curious about the exact scripts I use, you can grab them here. Trust me, they’re a great starting point!

#2: Story, Watch, Response

Real conversations stem from genuine interactions. A great way to spark one is by engaging with Stories.

Head over to your Instagram feed and take a look at the first five Stories from your non-real estate friends. Watch their videos, pay attention to what they’re sharing, and spend 30 seconds to a minute genuinely consuming their content.

Now, here’s the magic part: respond. Send a thoughtful message based on what you saw. It could be a comment, a question, or even just a compliment that shows you were paying attention.

Want to go the extra mile? Send a quick video response. A personalized video not only stands out but also makes the interaction feel more personal. Bonus tip: end your message with a question to keep the conversation going.

#3: Stay in the Story World

Did you know you can see exactly who’s watching your Stories? By tapping on your Story, you can view the list of everyone engaging with your content.

This is a goldmine for starting conversations. Let’s say you posted about your morning coffee ritual or a behind-the-scenes moment at work. Scroll through the viewers, pick a name, and send them a message inspired by the Story they watched.

For example: Hey [Name], I saw you checked out my Story about [topic]. Are you a coffee lover too? Small, specific comments like this can lead to big, meaningful conversations.

#4: Leverage Your Close Friends List

Here’s a feature that often goes underutilized: Instagram’s Close Friends list. This allows you to share Stories with a smaller, curated audience—marked by that little green circle.

Think of it as your inner circle. Add past clients, people in your sphere, or even potential future clients to this exclusive group. Then, start sharing more personal or behind-the-scenes content that feels special and authentic.

This is an amazing way to deepen relationships in a way that feels intentional and private. Whether it’s a sneak peek of your day or a casual update, these small touches can make your connections feel truly valued.

#5: Comment to DM

This might be my favorite strategy because it’s so natural. Take a recent comment from one of your posts and use it as a bridge to a direct message.

For example, if someone comments, I loved this video—it was so creative!don’t stop there. Head straight to their DMs and send them a quick message: Hey [Name], your comment made my day! I’m so glad you enjoyed the video. What part stood out to you most?

Even better, record a short video message to express your gratitude. The personal touch goes a long way, and it’s an easy way to take a public interaction into a private, more meaningful conversation.

Now, to get those DM scripts I promised you, click on the button below: 

Download 5 Ways to Start New Conversations on IG

If you found this helpful, make sure to share this BAM article with a real estate agent who has social media goals for 2025. 

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About the Author

Meet Krys Benyamein, the driving force behind Estate of Grace Real Estate. A trailblazer in video-first marketing, Krys helps lead his team to an average of 100 home sales per year. His journey from lawyer and public defender to realtor and investor showcases his diverse expertise. When not closing deals, Krys conquers mountains both figuratively and literally and recently summited Mount Everest, the tallest point on earth. He's a devoted family man, cherishing time with his wife, Paige, a plastic surgeon and their first child, Hendriks.

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