#192 – Why Plans with Friends Don’t Happen—and How to Fix It

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 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.

 


Listen to episode #192 on Apple, Spotify, YouTube, and anywhere you get your podcasts!

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LINKS 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

 

 


 

NOTE: the episode transcript can be found by scrolling down to the comments area.


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Nina Badzin hosts the podcast Dear Nina: Conversations About Friendship. She's been writing about friendship since 2014, co-leads the writing groups at ModernWell in Minneapolis, and reviews 30+ books a year on her website.

[00:00:00] Welcome to Dear Nina, conversations about friendship. I am your host, Nina Badzin. I have been writing about friendship for over 10 years. Podcasting about it for getting closer to five years.

Today is a solo episode. It’s actually a topic I’ve covered once before, but it keeps coming up, so I just wanna talk about it again. this is not an encore, this is not a rerun, this is a fresh episode. It’s just that we’ve talked about it before, and that is about making plans. The way that making plans works as adults,

when we’re in high school or even college and we have a lot of proximity with people, you live close by, you might live yelling distance across the hall, or you might live a block away, if it’s high school, you at least see each other in class. You run into each other at lunch, after school and activities, whatever it is, is much easier to make spontaneous plans.

And it would be wonderful if as adults we could do that too. And if you have a neighbor. Or you have somebody in an apartment [00:01:00] building that you get along really well with. You can do that. , You can spontaneously be like, I made so much soup. You wanna come over and have some, or, I really need a walk.

You wanna go for a walk? Even if you had no prior plans, no discussion about doing it, or you might even run into each other on the street. I’ve had that happen even in my neighborhood where I’m on a walk, I see someone else on a walk and we may join in. Doesn’t always work to do that.

Sometimes someone’s on the phone, but that’s spontaneous. That’s wonderful. It doesn’t happen that much as adults. So if spontaneous plans aren’t gonna happen that much as an adult, how are you going to make plans? You’re going to have to put those plans on the calendar and it’s not fun and it’s annoying and everybody hates this part about.

Well, not everybody, some people don’t mind it, but a lot of people really don’t like this part about making plans. They either don’t want to be booked that far in advance, okay? So that’s not gonna work for everybody. But if you have a friend who doesn’t mind being booked far in advance and you don’t mind being booked far in advance, that is a great way to see each other.

If you have a friend who likes things to be more [00:02:00] spontaneous. Okay, that’s fine. But you may have to put it on them sometimes that they should reach out to you. Then that’s a discussion that you need to have with your friend. Hey, I like to have things booked. You like things to be spontaneous. We wanna see each other sometimes.

How do we meet in the middle? that is a discussion to have with your friends. That is my response when you say to me, ’cause sometimes you guys do as listeners or members of my Facebook group at Dear Nina, the group, you might say, well, Nina, not everybody makes plans that way.

I agree, but you still have to figure out then how you are going to see your friend. If you won’t put plans on your calendar or your friends won’t put plans on the calendar, the two of you are going to have to have a discussion if you wanna see each other, where you acknowledge that, where you say, Hey, we don’t really match up in the way we make plans.

How can we figure out a way to see each other and the two of you figure it out. But as long as you communicate that we have an issue here, the issue being it’s a good problem actually. The issue being we actually want to see each other. I wouldn’t even call that a problem. It is a problem, but it’s a good problem. The problem being, [00:03:00] I like you, you like me, we wanna spend time together. We can’t seem to figure out how to make it work because the ideal way I am, sorry, I, I have to give an opinion here. The ideal way here is if you wanna see somebody, if you want to make plans with somebody and you reach out, you wanna go for a walk, you wanna go for dinner, you wanna go to lunch, there’s this museum with an exhibit in town for the next two months.

It’d be really fun to go see it in order for that event to actually happen, it has to get scheduled. I don’t really see any other way unless, like I said, both of you can meet spontaneous. Wonderful. That’s great. I’m not being sarcastic. I actually think that’s great. It is so nice when things don’t have to be so booked out, but because of the reality of life and all the different things, people are juggling, their friendships,

being just one of them. Their friendship with you and your friendship with that person being just one of perhaps several friendships. Scheduling is often what it takes. Now it’s not always ahead of time. I just, this past weekend, [00:04:00] looked at my calendar, noticed that my husband and son had. Something they were doing that my daughter had, something she was doing.

My other two kids are in college or abroad and not in the house. I had the data myself. It was wonderful. I had a lot of work to do , I love a Sunday where I unexpectedly get to catch up with work. However, I do need to exercise. I’m having a lot of back issues. It’s a kind of a recurring back problem I have mostly caused by sitting too much on this computer.

Not just recording ’cause that doesn’t even take that long. It’s the editing and all of the writing and all of that, that puts a lot of pressure on my back. The only solution is to move. So I’m like, okay, I could get on the treadmill, but I don’t really wanna do that.

So I noticed my big open day and I reached out to a friend I haven’t seen in a long time, and it was actually kind of a funny story.

If she hears this, she’ll laugh. We normally go out as couples. I don’t see this friend so much for a walk, mostly because of her work schedule and my weekend schedule. She works a lot during the week , and on the weekend I have other obligations during the day that make [00:05:00] me not so easy to schedule with on a weekend day, happen to be this Sunday wide open. So I texted her and said, Hey, do you wanna walk

i’m open all day. I could do morning, afternoon, She didn’t think I meant it for her. she texted back, did you mean this for me? And she thought I maybe got the name wrong. I was like, no. Yes for you. I really wanna see you. I’d love to catch up. I know it’s last minute. I mean, I, this was Saturday night.

I texted her for Sunday. Can you walk? And she told me when she was available, she had some kids sports things to, she said, I can do one o’clock. I said, I will make one o’clock work. ’cause I wanted to see her. I was wide open. That was a wonderful, spontaneous situation. For me that does not happen that much.

So what is the way to make plans. I did write in a newsletter about this, uh, a while ago. Let’s see when, this is from December, 2024. So it was actually a really popular post, uh, for substack. A lot of times on Substack. Uh, people don’t comment a lot. this one had a decent amount of comments, lots of hearts.

[00:06:00] again, you find my substack@dearnina.substack.com. Before I read you, my favorite part of it, I’m going to tell you that it was another example of scheduling success.

That is what I wrote about so different than this spontaneous one. I said Readers, some major scheduling successes with friends happen this week. First, a friend who lives an hour away wanted to make a lunch plan with me and two other friends.

Her text was a masterpiece. She did not text. Let’s get together for lunch. She did not text. When can we get together for lunch? She texted something like. Lunch in January. She offered plenty of dates to choose from and it did not take long to get a plan on our calendars. Easy done. A similar interaction happened days later.

There are a few women I play Mahjong with from time to time. It had been a while since we last played, so one of the women did something simple and so appreciated. She did not text. Who wants to play mj? She did not text. When can we play mj? [00:07:00] She stated that she misses us, wants to play, and offered yes, plenty of dates to choose from within the hour.

We had a specific plan for a few weeks from now. Easy done.

I thought this is episode 1 21 in action, so 1 21, just to interrupt myself, here was the other one I talked about on how to make plans. In that episode, I had read two anonymous letters dealing with different issues where the letter writer was struggling with scheduling plans with their friends. And in my answer to that letter, I admitted that I often make it my problem to get out the calendar.

First, I look at my calendar and I throw out dates when I’m the one suggesting plans. I think that’s the right way to go about it when you’re suggesting plans. So it doesn’t bug me, but I also seem to do it. If the other person starts with Let’s walk or something like that, why am I the one suggesting the dates in those second scenarios?

It’s probably a desire to show that I’m genuinely interested, plus an itch to delete items from my various inboxes.

I’m just gonna [00:08:00] continue reading this to you because it’s actually in a way faster than me just re-explaining it because I already wrote it more straightforward. So continuing what I wrote, I said,

let’s acknowledge that it’s extra labor to always be the one poking around your calendar to suggest dates. There’s no actual rules to this, but I think if you suggest the plans, you should also suggest the dates. if you cancel the plans, you should suggest new dates.

And if you are the invitee who cannot hang out on any of the dates your friend suggested, then it’s your turn to scour the calendar and offer alternatives, assuming you’re interested, which perhaps you’re not. and that’s a whole other issue by the way, listeners, which I have gotten into.

I did an episode, it was episode 73 with Ruhi Covell, and the title of that episode was, I’m just not into this friendship. So that’s a whole different issue. We’re not gonna address that here, but obviously it does connect to the plan making issue. If someone is trying to reach out to you for plans and offers, dates, let’s say, the way I’m suggesting they do, and you actually don’t wanna get together at all.

I understand that. That is very tricky. Then I [00:09:00] wrote, you might be thinking, but Nina, nobody’s ever asking me for plans. If you have ever listened to my podcast, you know, I will say that most people are terrible at number one, reaching out and number two, making plans. You should absolutely not wait for other people to make plans.

If you want plans. Make the plans, and if you want those plans to happen at a certain time and place, then you suggest the dates, times, and locations. Like I said, there are no rules here, but one thing is certain, if you are always waiting for other people to reach out, then you will not have as many things to do with friends.

So I had made a goal for myself. At that time when I wrote that to let a little time simmer between when somebody reaches out to me and says, let’s walk. And when I immediately throw out dates, because I do think I have trained the people in my life to expect that I’m gonna do the dates and if I want other people to throw the dates out, which like I said, is the worst part about making plans.

Going into your calendar and figuring out, okay, on this day I have a dentist appointment and I’m working at these days, and I have. [00:10:00] Something for the kids on this other day, and then you find these little pockets of time when you could walk or you could have coffee. That takes a lot of work, and if you’re always the one doing that work, it is frustrating.

So the only way to get your friend to start doing it is you may have to say, when they suggest a plan, great. Throw me some dates. You can’t always be the one to do it. However I want to talk to you now. If you’re never the one who does it, if you never suggest dates, if you are running around texting people and being like, I miss you.

I miss you. Let’s get together. No, you have to send dates. Again if you wanna be spontaneous, then that’s fine. Then do it two days before. Do it the night before, like I just did with my friend the night before. Say tomorrow sometime I wanna walk. I am free between one and three. Can you walk any of those times?

If they can’t, that’s okay. You’ll think of them the next time that you have some free time, or maybe they’ll think of you the next time they have some free time. There isn’t just one way to do this, but it is true that if you never take out your calendar, [00:11:00] even if it’s the day before and say, can you do whatever it is you wanna suggest?

You won’t see that person unless it’s someone who lives next door. Or in the same building or down the block, and you wanna count on running into them, and that is the time you’re gonna see them and say, oh, we should grab dinner tonight. Wonderful. If that works for you. It does not work for most people.

. And a big part of maintaining a friendship is seeing that person face to face, not just through text, certainly not just through social media, and not even just on the phone. Actually seeing that person, seeing their facial expressions, hearing the warmth in their voice, catching up, and maybe even more than catching up, having an experience together.

A walk is an experience that’s better than nothing for sure. Maybe you can go do something together. Maybe on that walk you discover that you both really are interested in this speaker who’s coming to town and you wouldn’t have stumbled on that ’cause that’s not something you’re gonna randomly text about.

That’s something that came out through the walk, through the coffee, [00:12:00] through the lunch, and now on the spot, you can both take out your phone and make a plan to do the next thing. I know this all sounds really obvious. The reason I am bringing it up is because it comes up in my direction a lot.

I am the recipient of a lot of anonymous letters and anonymous comments on Facebook and messages on Instagram and TikTok. People are struggling with seeing their friends. People are struggling with making plans. People are struggling with feeling like they are always the one that reaches out. That’s a whole different topic.

I say it a lot. I’m gonna encourage you here too, to not keep track of who reaches out. You will be happiest you just reach out anyway if you feel like that friend is taking you for granted. If you feel like that friend is only reluctantly making plans with you, then ask someone else. But if you wanna have plans, if you wanna stay social, if you want to have things on your calendar, if you wanna see people in person, then never wait.

You make the plan. Okay, that is it for today for a solo episode. I think people could only take so much [00:13:00] of my voice without interruption, so I’m just going to say right now. I hope you’ll come back next week. I have some great episodes coming up with guests, I will see you there.

Come back next week when our friendships are going well. We are happier all around.

Nina: Listeners, you can find my Facebook group. Dear Nina, the group, when you go into the search part of Facebook, type in Dear Nina, the group, and that is a great place where you can get your anonymous friendship questions answered, not just by me, but by other active members of the group they can even answer from the other point of view, because it’s so many people coming together who care about friendship and think about it a lot.

And if we’re not connected on social media, that’s at Dear Nina. Friendship on Instagram and TikTok, even on YouTube if you wanna see the episodes. All right, have a great week.

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Hi, I'm Nina

HI, I’M NINA BADZIN. I’m a writer fascinated by the dynamics of friendship, and I’ve been answering anonymous advice questions on the topic since 2014. I now also answer them on my podcast, Dear Nina! I’m a creative writing instructor at ModernWell in Minneapolis, a freelance writer and editor, and an avid reader who reviews 50 books a year. Welcome to my site! 

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Hi, I'm Nina

DEAR NINA: Conversations About Friendship is a podcast and newsletter about the ups and downs of adult friendship. I’m the host, Nina Badzin, a Minneapolis-based writer who accepted a position as a friendship advice columnist in 2014 and never stopped. DEAR NINA, the podcast, started in 2021, and has been referenced in The Wall Street JournalThe Washington PostTime Magazine, The GuardianThe Chicago TribuneThe Minneapolis Star Tribune, and elsewhere

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