Navigating friendship when your planning styles don’t match

Why is it so hard to actually make plans with friends as adults? In this solo episode, I’m digging into one of the most common (and frustrating) dynamics in friendship: when one person likes to plan ahead and the other prefers to keep things spontaneous. I also discuss when both people like to have an actual plan, but one friend is doing most of the work of sending dates.

I talk through why this mismatch can stall even strong friendships and what to do about it. From turning vague “we should get together” texts into real plans, to figuring out when it’s your turn to suggest dates, this is a practical, honest look at how to actually see your friends more often.

Here’s the part I’ll say plainly: if a plan doesn’t get on the calendar, it usually doesn’t happen. That’s just the reality of adult life. But that doesn’t mean there’s only one “right” way to make plans or that being spontaneous "never" works. But having good intentions to "get together" aren't enough to sustain a friendship.

Inside this episode, I discuss:

• Why spontaneous plans feel great—but don’t happen as often as we wish
• What to do when your friend doesn’t like booking things in advance
• How to meet in the middle without overcomplicating it
• The small shift that turns “we should get together” into an actual plan
• When it’s your turn to suggest the dates (It can't always fall on the other person. You have to open up your calendar, too!)

I also share a couple of real-life examples—one where spontaneity worked, and one where clear scheduling made everything easy—to show how both approaches can work when you’re intentional about it.

This isn’t about forcing your style onto someone else. It’s about acknowledging the mismatch and actually talking about it because the “problem” here is a good one: you and your friend theoretically want to spend time together. And if that’s the case, there’s always a way to figure it out.

If you’ve ever felt like you’re always the one making the plans, or you’re waiting around for plans that never happen, or you just can’t seem to sync up with a friend you really like—this episode will give you a realistic way forward.

LINK MENTIONED: 

Episode 73 with guest Ruchi Koval: "I'm Just Not Into This Friendship"

Episode 121: "Rules For Making Plans with Friends" 

"This is How to Make Plans With Friends" on Substack, Dec 2024 

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Special thank you, as always, to my assistant producer, Rebekah Jacobs!