Five with Fry
Five with Fry is your go-to podcast for understanding conflict—where it comes from, why it shows up, and how to handle it with clarity and intention. On each episode, Dr. Jen Fry breaks down the moments we avoid, the reactions we default to, and the skills it takes to move through conflict without blowing things up or shutting down.
Five with Fry
48: Why The First Boundary Is Easy And The Fifth Is Brutal
The first “no” is brave. The fifth “no”? That’s the one that tells people you’re serious.
In this episode, we dig into a very real holiday scenario: you set a simple boundary—if grandpa uses slurs, I’m leaving—and suddenly the family group chat is acting like you’re detonating the traditions of the free world. Your sibling says “just ignore it,” your aunt pulls the “he doesn’t have much time” card, and somehow you become the problem for wanting a slur-free meal.
We break down why people who love you still push your limits, how family systems protect their comfort at all costs, and what to say in the moment so you don’t slip into a 20-minute TED Talk. You’ll get grounded, repeatable scripts you can actually use, plus the logistics that make boundaries stick: share it early, plan your exit, and pick one steady line you can return to when things get loud.
If the line does get crossed, we walk through how to leave without theatrics, how to send a short follow-up that connects action to boundary, and how to handle the fatigue that shows up afterward. Your nervous system needs reps before this gets easier, and consistency is what teaches people where your line actually is.
Expect some pushback. Expect some clarity, too. Boundaries get real in repetition.
If this episode gives you a line you can use at the table, pass it to someone else who needs backup this season. And if there’s a topic you want me to get into next, send it my way.
Friends, welcome to Five with Friday, where five is the magic number. Whether it's five minutes, five questions, or anything that fits in five. I dive into the big topics that matter, sometimes alone and other times with a friend. From navigating sports, conflict, to family dynamics, travel, tech, hard-hitting issues, and even politics. Nothing, and I mean nothing's off the table. This is where curiosity meets conversation, and we always sit at an intersection. I'm your host, Dr. Jen Fry of Gen Fry Talks. Let's get into it. So today we're gonna talk about boundary setting and why the first boundary that you set might actually be the easiest one you're gonna set. And I know you're sitting there saying, Jen, that doesn't make any sense. It's really hard. I'm not saying it's not hard. What I am saying is that when you have to continue refirming those boundaries, that's when it gets to be really, really difficult. And many times people don't think about that. They're only thinking about that first boundary that they have to set. And that makes sense. They're like, I ain't got time for these other boundaries. But I want you to imagine you tell your parents at Thanksgiving, if grandpa says these things, I'm gonna leave. And you're like, I just want to let you know if this happens, I'm leaving. So you've set that boundary. Well, then guess what's gonna happen? Your siblings call. And they're like, Jen, come on now. You know grandpa says stuff, just ignore it. We don't know if he's gonna be living tomorrow. Just go into the room, you'll be fine. So then that's now the second time you're gonna have to affirm it and say, you know what? I hear what you're saying. But if grandpa says this thing, I'm gonna leave. But then guess what? Your favorite aunt calls you. And then she says, Baby, I know grandpa's frustrating, but he only has a few years to live, and I don't even get to see you that often. So you can't just be leaving because grandpa says something we know he's gonna say. Just ignore him, we can go into the room, it'll be fine. So now you've had to say it a third time. And then your favorite uncles call you, and they're like, This is the first time I've been home in years, and we really want to see you. Please don't let grandpa, who was raised this way, ruin seeing you. And so now you're having to set it a fourth time. So we've just had to set it four times, and so now we're gonna be feeling exhausted and pressured. And then mom's gonna circle back and say, You can't leave because grandpa says these type of things. You know he's gonna say that, but we can't say anything to him because he'll get really upset. So just go into the kitchen. I made your favorite dessert, and just tolerate him, but you can't leave the house. So now you have to set it five times, and the event hasn't even happened, and so that's why I'm telling you that sometimes setting that first boundary, even though you might not realize it, is actually gonna be easy peasy. The problem is when you have to keep setting the boundary over and over again because you're gonna get worn down, and then something's gonna just start in your ear and say, you know what? I can just go into the other room. You know what? He's only gonna live for so long. You know what? So-and-so is right. And then that boundary that you were so fierce with having absolutely disintegrates because you had all these different people pretty much telling you to ignore the boundary. And so that's why when you're gonna give a boundary, you've got to know that people are habitual line steppers, they don't like boundaries, so they will keep finding all the different ways to make you not have that boundary because it's in it's uncomfortable and inconvenient for them. It's uncomfortable for them to have to back you up with grandpa saying stuff. It's unconvenient and uncomfortable for them to have to say something when they've never said something and they've let him just say whatever he's wanted for years. And people don't want that. So they're gonna stop you because they don't want to do that. So when you're gonna set boundaries, I need you just to be prepared for all your family members to try and stop you from having that boundary. But you, my friend, can do it. Well, friends, that's it for this episode of Five with Fry. Your dose of five insights, ideas, and inspiration. If you love what you heard, don't forget to head over to where podcasts are played to subscribe, share, and leave a review. Got a topic you want us to tackle? Drop us a message. We love to hear from you. You can come follow me on IG, Twitter, the TikTok, at Genfry Talks, or join me on LinkedIn. Look for me at Dr. Genfry. Until next time, stay curious, stay bold, and keep the conversation going. See you on the next Five with Fry.