I want to tell you something that might make you feel a lot better about yourself.
Millions of people are sitting alone behind their phones and laptops right now, typing some version of the same question into a search bar: how do I ask someone to hang out without making it weird?
Millions.
So if you’ve ever had a great conversation with someone at pickup or at work or at a party, thought “I really like this person,” and then… done absolutely nothing about it? You are not broken. You are not socially inept. You are just a person living in a time when nobody taught us how to do this.
That’s what this episode is about. How to ask someone to hang out, what to say, how to handle rejection, and why the awkwardness you feel when you finally DO make the ask is not a sign that something is wrong. It’s actually the best part.
Why Making Friends as an Adult Is Actually Hard (It’s Not Just You)
Before we get into the practical stuff, I want to spend a minute on the “why.” Because I think a lot of us are walking around with this low-grade shame about the fact that making new friends feels so HARD, and we’re quietly convinced that everyone else has figured it out.
They haven’t.
When we were kids, we had proximity working for us constantly. Same school, same soccer team, same neighborhood. We saw the same people over and over without doing anything to make it happen. And beyond proximity, someone else was handling much of the relationship admin. Our parents planned the playdates. Our teachers helped us navigate the conflict on the playground. Our coaches built the team culture. We were just… showing up.
And then we grew up.
Now, think about how many relationships you’re actually responsible for maintaining as an adult. A partner, maybe. Your parents. Siblings. Your kids. Old friends from high school and college. New friends you’ve made in your adult life. Coworkers. Neighbors. Gym friends. Book club people. Friends of friends. Every single one of those connections requires YOU to put in some kind of effort to keep it alive.
And here’s the part nobody talks about: we’re doing all of this without the proximity safety net, without the built-in guidance, and often without even the cultural permission to say “I want more friends.” We’ve been told, at various points in our lives, that the MOST important relationship is the parental one, then the friendship one, then the romantic one, then the family one… and everyone’s arguing about which one deserves the top spot.
Meanwhile, I’m just sitting here thinking: what if they all mattered? What if, instead of ranking them, we actually learned how to manage them all at once?
That’s a bigger conversation. But I bring it up because if you’re wondering why it’s so hard to make friends as an adult, I want you to understand it’s not a personal failing. It’s a structural one. Most of us were never taught how to do this. (And I didn’t even get into the infrastructure problems, like the lack of third spaces or walkable neighborhoods. I have whole episodes on those.)
You can listen to the full episode for the complete breakdown of why adult friendship feels so much harder than it should, and why that has almost nothing to do with you personally.
The Actual Ask: How to Do It
Okay. Practical stuff. Let’s go.
First: in person or over text?
Honestly? It depends. If you see this person regularly, like at school drop-off or in the office, an in-person ask is great. But if you have so much anxiety about it that you’re worried you’ll fumble your words or say something weird, then do it over text. The BEST method is whatever one actually gets you to make the ask. That’s it. That’s the whole answer.
Second: be specific.
This is the one I really want you to hear. Before you walk up to someone or send that message, have an idea ready. Not “we should hang out sometime.” An actual thing. A place, an activity, a time.
I know what you’re thinking: “But I don’t know what they’re into.” Pick something anyway. Here’s why.
If you ask me to go to Zumba, I’m going to say no. Not because I don’t like you, but because I am genuinely terrible at Zumba. I’m the person who goes right when everyone goes left. I once had two of my closest friends literally flank me on either side in a Zumba class in college to try to insulate the rest of the room from me. It didn’t fully work.
So if you ask me to Zumba and I say no, what happens next? I probably tell you that story. You learn something about me. Maybe you say, “Okay, what about spin?” And I tell you I still can’t follow choreography but at least I won’t run into anyone. And then maybe I say, honestly, a walk would be so much easier. And now you know: I’m uncoordinated, I’d do spin, but my preference is a walk.
You learned ALL of that just because you offered something specific instead of saying, “I don’t know, what do you want to do?” A specific ask creates a real conversation. It gives the other person something to react to, and it gives you something to learn from.
Third: get it on the calendar.
Don’t let the conversation end with “yeah, we should totally do that.” Keep going. What day? What time? Where are you meeting? Who’s confirming?
The faster you can nail down the who, what, where, and when, the less room there is for it to dissolve into a string of texts that goes nowhere, and the less ambiguity about who’s actually responsible for following up.
When They Say No (And They Might)
Here is the reframe I want you to carry with you: when someone says no, they are rejecting your offer. Not you.
I know. In the moment, when your nervous system is convinced you’re being chased by a cheetah because someone turned down your Zumba invite, that distinction feels impossible to hold onto. But it’s real.
Think about it. You don’t really know this person yet. They don’t really know you. We let strangers into our orbit all the time, at the coffee shop, at the farmer’s market, at school pickup. It doesn’t take much. So if someone is saying no to a hangout, it is far more likely that something in THEIR life is making it hard to say yes than that they’ve decided they don’t like you.
Maybe they’re in survival mode and can’t add a single thing to their plate. Maybe they’re quietly dealing with something you don’t know about. Maybe they’re someone who’s scared to open up to new people, and your ask caught them off guard. Maybe you asked them to get drinks, and they’re working on their relationship with alcohol, and that has nothing to do with you at all.
So how many times do you try? There’s no perfect answer. A lot of people use three as a benchmark. Three rejected offers, and if you haven’t gotten anything back, you let it go. Some people reset the count if the other person initiates something in between, even if you couldn’t make it. Whatever feels right to you. But please try more than once. Because “no” very often just means “not now.”
And if you do eventually let it go? That’s okay too. It doesn’t mean they dislike you. It might mean that making new connections just isn’t their priority right now, and that’s a completely separate thing from how they feel about you as a person.
If rejection is the thing that’s been holding you back from making friends as an adult, go listen to Episode 145, Reframing Rejection with Tanesha Moody. It will shift how you think about this in a real way.
What If They Cancel? What If They Ghost?
You did everything right. You made the specific ask. You got it on the calendar. And then Tuesday at 5pm rolls around, and they cancel.
That genuinely stinks. I’m sorry.
First question: Did they try to reschedule? If they offered a new time, take that seriously. That’s a good sign. If they didn’t reschedule and just… disappeared, here’s the thing to remember: this person is someone you barely know yet. They don’t have the same roots with you that a decade-long friend would have. That also means they’re more likely to cancel when life gets overwhelming, because the connection isn’t yet a huge priority for them. It’s not about you. It’s about where they are.
Ghosting is a different kind of sting. My suggestion: reach out once. Just once. If they respond, approach it with genuine curiosity. You don’t know them well enough yet to know how they handle hard or awkward situations. Maybe they’re someone who goes quiet when things get complicated. If they don’t respond at all, let it go. You may never know why. And that’s one of the genuinely hard parts of this whole process.
But here’s what I want you to hold onto: rejection, cancellation, ghosting… all of it is a normal part of what happens when you try something new. It’s not evidence that you’re doing it wrong. It’s just evidence that you’re doing it.
Tune into the full episode for more on how to handle each of these scenarios, including what to do when someone gives you an ambivalent “yes” and you can’t tell if they actually want to hang out.
When Connection Is Your Priority But Not Theirs
This one doesn’t get talked about enough.
You’re here. You’re listening to a podcast about friendship. You are INTENTIONAL about this. But the person you just asked to hang out? Maybe they haven’t thought about making new friends in years. Maybe they closed that door a long time ago and assumed it wasn’t really an option anymore. Maybe they know connection is possible, but their brain is completely consumed by something else right now, like getting their finances in order, or a health thing they haven’t told anyone about, or a caregiving situation that’s quietly eating all their capacity.
When someone gives you a weird yes, or a hesitant yes, or keeps saying no but also says “keep asking,” it doesn’t always mean they don’t like you. It might just mean that you’re operating on different priority levels right now.
One thing you can try: instead of asking them to carve out new time, see if you can join something they’re already doing. They take their kid to the neighborhood park every Saturday? Ask if you can meet them there. They’re going to the school fundraiser anyway? Can you find each other when you’re both there? This removes the ask of “make space for me” and replaces it with “I’ll come to where you already are.” If they’re hesitant even about THAT, it might be a sign to redirect your energy. But even then, it’s not a foolproof read. You don’t always know what’s happening on their end.
And if you’re always the one initiating? That’s worth noticing. It might mean connection is your priority and not theirs, but they’re willing to show up when you make it easy. It might also just mean that this person has never learned how to be an initiator, and they show up in other ways once you’re actually in the friendship. I have friends like that. One of them is a terrible initiator but an incredible planner. Once I get her on the calendar, she comes up with the most fun, spontaneous ideas. That works for me. It might not work for you. But it’s worth getting curious about before you write someone off.
Taking a Friendship Deeper (Yes, This Applies Too)
Real quick, because I think this comes up a lot: what about asking a friend you already HAVE to hang out in a new way?
The gym friend you want to actually get coffee with. The work friend you want to invite to your birthday dinner. The neighbor you’ve chatted with a hundred times but never actually made plans with. How do you take someone from “friend in context” to just… friend?
It’s going to feel a lot like asking someone brand new. A little awkward. A little vulnerable. And that’s okay. The difference is that you already know things about this person. You know what they’re into, what makes them laugh, what their schedule looks like. So you can make a more informed, specific ask. And if they say no, you have enough of a foundation to say “okay, what WOULD work?” and actually figure it out together.
The goal is just to find one new way to connect outside the context you already share. That’s it. One thing. And yes, it might be a little awkward the first time. That’s fine. Keep reading.
The Awkwardness Is Actually the Point
Here’s the thing I really want to leave you with.
When you make the ask, and they say yes, and you actually show up for that walk or that coffee or that Zumba class you both agreed to try even though neither of you is good at it… it might be a little awkward. That’s okay. It doesn’t mean you’re not compatible. It doesn’t mean you made a mistake. It just means it’s new.
And here’s what I’ve noticed: when people talk about their oldest, closest friendships, the stories they tell with the MOST warmth are almost always from the beginning. The weird first hangout. The thing that didn’t go as planned. The moment when someone said something awkward, and you both laughed about it for years.
We spend so much energy trying to skip that phase. But you can’t. And honestly? You shouldn’t want to. Because the awkwardness is the first chapter of the story you’re going to be telling for years.
So here’s your challenge this week: ask one person to hang out. Pick something specific. Get it on the calendar. And if it’s a little weird when you actually show up? Good. That means you’re doing it right.
If any of this resonated, listen to the full episode at friendshipirl.com/episode167 for everything we covered, including how to read the signals when someone’s yes doesn’t quite feel like a yes, and why “no” almost never means what you think it means.
Resources Mentioned
