How to Ask Someone to Hang Out (Without Making It Weird)

Ever feel both happy and also … a little jealous when a friend shares good news?I experienced this dichotomy the other night, when my friend shared a success. I found myself performing enthusiasm while dealing with conflicted emotions; I wanted that kind of success, too. Did this make me a bad friend for feeling something other than pure joy for her?In this episode I talk about jealousy in friendship: how it happens, for all things big and small; the different ways it might manifest; and how acknowledging it can shift your friendship culture in a deep way.I think the goal is not to have no feelings. It’s to let the feelings tell you something useful – and then bring that information back to your friendship.In this episode you’ll hear about:Envy vs. jealousy in friendships, and processing each through self reflection and honest conversationsHow to avoid the distance and awkwardness that jealousy or envy can provoke in friendshipsThe internal struggle of performing enthusiasm while dealing with conflicting emotionsWhy envying somebody famous feels so different from envying a friendResources & LinksLike what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

While brainstorming episode ideas, I sometimes search Google Analytics to see what people are asking. Here’s what I found this week: How do I ask someone to hang out without making it weird?Turns out, millions of people are feeling anxious about asking someone to join them for coffee! (What do I say? What if they think I’m weird? What if they say no?)Today, we end that cycle. I’ll talk you through how to ask someone to hang out: what to say, how to handle rejection, why it feels hard.Embrace that awkward first encounter! That’s the kind of thing you laugh about later on, years into a friendship.In this episode you’ll hear about:Why asking someone to hang out feels so much harder as an adult than when you’re a kid or teenagerThe value in being specific when asking someone to hang out and suggesting an activity or timeThe importance of not taking rejections personally! Rejection is of the offer, not of the person; others might not be prioritizing connection right now as highly as you areHow to make it easier to ask somebody to hang out by choosing an activity they’re already partaking inResources & LinksListen to Episode 145 about reframing rejection with Tanisha Moody, Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

She used to call herself the shy, awkward kid with one best friend. Now she calls community her superpower. Last year, Alison Kinsey decided to run an experiment: invite 10 interesting people to coffee in one year. The result? New friendships and a complete shift in how she sees herself.And you’d never guess it was a cross-country move to California that encouraged her to become an initiator. From afar, I’ve seen Alison start networking groups, go on blind double dates, host low-effort gatherings, and get deeply involved in her local community.Alison is also one half of the Podcasting for Creatives team (and host of the podcast, Real Time Creator), who I have been working with since this podcast was just an idea. If you have been telling yourself “I’m too introverted” or “I’m just bad at this” —  that story is not permanent. If you keep showing up, you'll look back and realize you're not the same person anymore. In this episode you’ll hear about:How Alison’s move to San Diego triggered her to become more intentional about her friendships, starting with connecting with the organizer of a Meetup groupHow Alison used Instagram as a kind of “friendship dating app” to find and connect with people in her communityReal Time Creator, which documents Alison’s career break from being a high-earning breadwinner to taking a creative sabbaticalAlison’s challenge to have coffee with 10 new people over the course of a year, and her experience organizing low-stakes hangoutsResources & LinksFind Alison on Instagram, LinkedIn, and her podcast Real Time Creator, which documents her layoff from tech and creative sabbatical. Learn more about my podcast editing team, Podcasting for Creatives.Listen to Episode 12 about the Roots framework; Episode 14 about friend groups; Episode 44 about how making friends can help you with the big life choices; Episode 48 about using the internet to find connections; Episode 83 about making friends in different life stages; and Episode 134 about fringe friends.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

This is the second installment in a two-part series about group chat anxiety.If having a massive group chat text chain stresses you out, then I’m going to let you in on a secret: it’s because you CARE about your friendships. But with these chains, we’re also sometimes pouring this caring into the wrong place.In this episode, I talk about auditing these group chats and determining what’s working and what’s draining. How can we use them, not as a primary source of connection, but as a tool to move toward connection that feels fulfilling?With a little effort, hopefully this extra thought will mean we’re texting a little less with the intention of connecting a little more.In this episode you’ll hear about:Looking at how your group chats are functioning: is it to update a large group of friends? Is it a smaller group? What’s the purpose of the group chat?Having conversations with your friends about what the group chats are for; for example, are side conversations okay? Is it okay to add new people to the chat? Etc.Giving yourself permission to set boundaries: you don’t have to be in every chat, you can mute or leave, and you can set response windowsIn my opinion, the wrong kind of group chat work (constantly checking, crafting perfect replies) vs. the right work (auditing chats, investing energy where it matters)Resources & LinksListen to Episode 161 about managing friendship overload and relationship burnout.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

Have you ever picked up your phone and discovered a hundred unread text messages?Likely you’re at the tail end of a group chat, and it kind of feels like walking into a party two hours late. You want to respond but wonder: will people be annoyed at you for backtracking? Maybe you even feel resentful for being added to this chat without consent. Group chats can sometimes feel like you’re operating with one arm behind your back – but if you suffer group chat anxiety, I think it’s important to remember that it’s because you really care about your friendships.This episode is the first segment of a two-part series on anxiety surrounding group chats: today, we’re talking about why group chats can be tricky to navigate, and in the next, what you can actually do about it.In this episode you’ll hear about:Why group chats are often used to satisfy a craving for connection but often fall short of delivering real connection people wantThe richness of in-person connection (Body language! Tone! Shared moments!) vs. the flatness of textingDifferent ways group chats can cause anxiety, from the public nature of having something you said responded to or ignored to lurker guiltThe intensity overload of group chats, plus, different studies about texting and anxietyResources & LinksListen to Episode 12 and learn about my theory about the Roots framework; Episode 100 about the Wheel of Connection; Episode 127 about using data to manage your friendship mental load; Episode 131 about the spectrum of digital connection; and Episode 134 about fringe friends.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

When Michelle Valiukenas lost her daughter Colette after being born at 24 weeks, the grief was devastating – and this grief had real effects on her friendships, both good and bad.In today’s episode, Michelle and I talk about the evolution of relationships through all of life’s ups and downs and the value of showing up imperfectly.Shortly after recording, my own friends lost their son in the NICU, and I felt uncertain how to go about sharing this episode; I decided to release it because my friend told me these kinds of stories provide her comfort and can be hard to find.If you're supporting someone through grief, or if you're in it yourself, I hope that this conversation gives you permission to have the hard conversations. In this episode you’ll hear about:The power in giving our grieving friends the options of whether they want to talk about their loss or not How I used this episode to show up for my own grieving friends, including normalizing talking about the the child they lost, Cam, and being present through hard daysWhy we can’t maintain our friendship peaks forever, just as you can’t sustain race-day conditioning – and that’s OKWhat’s actually helpful for people grieving, from remembering anniversaries to offering concrete help (i.e., don’t ask what they need, offer a service instead)Resources & LinksListen to Episode 12 and learn about my theory about the Roots Framework.Michelle and her husband founded the Colette Louise Tisdahl Foundation, which aims to improve outcomes of pregnancy, childbirth, prematurity and infancy, and help the grieving process. Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

One reason I do this work is I believe all humans deserve to feel safe – but for a lot of us, that’s not a reality right now. Across the country, from Minneapolis to Maine, people, including children, are being kidnapped from their homes under the guise of immigration crackdown. So today’s episode is about leveraging connection as a form of resistance to protect our neighbors. What can you offer, and how do you present yourself as a safe person?You might think the action ideas in this episode are too small. But resistance doesn’t always have to be on the front lines. You can be the neighbor somebody calls in an emergency. You can pay attention and let people who might do harm know you’re watching. It all adds up.In this episode you’ll hear about:Ideas for how to present yourself as a safe person, from hanging rainbow flags or multilingual signs to simply talking about your values in casual conversationThe truth about numbers: when people who help outnumber those who’d harm, it becomes harder for hateful actors to actWhy not all resistance is viral and the real value in small, everyday connections and actions, particularly when crises hitHow to help, from calling congressional representatives to watching for opportunities in which you can show upResources & LinksListen to Episode 120 where I dive into my political beliefs and Episode 126 about how friendship can be a vehicle for radical change.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

Ever feel like, all of a sudden, you have TOO many friendships to juggle?I know – this sounds like the most privileged problem ever! But truly, it’s a common experience, and I think the reason some of us get burnt out is because we feel we need to show up for each person in the same way. My thoughts? Some friends are lifelines; others add color to your life. Both types matter. But you don’t have to show up the same way for everyone. Whether you’re feeling stretched thin by your growing network or just want to be more intentional about how you connect, this episode offers a practical approach to keeping all your many friendships meaningful AND sustainable. In this episode you’ll hear about:Why you don’t have to show up the same way for every friend, and how redefining your relationship roles can save you from burnoutHow your growing list of responsibilities and roles as an adult naturally leads to more connections — and why that’s a good thingGetting clear on your unique strengths in friendships so you can show up where it matters most (and release the guilt of not being everything to everyone)Resources & LinksListen to some of my episodes that challenge the “all-or-nothing” mindset about friendship, including Episode 13 and Episode 33. And be sure to listen to Episode 12 about the different kinds of friendship roots.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

Have I made it sound like it’s easy to keep friendships strong and resilient?If so, let me set the record straight: making changes in friendships, even if they’re for the better, is HARD. A lot of the time, it involves uncomfortable conversations, confrontation, and hard feelings. It’s so tempting to push problems aside to keep relations “peaceful.”I think there’s an expectation to put in work for romantic and familial relationships, but how much work should we be doing for friendships? At what point is it not worth the effort? Here’s my hard truth: If you want friendships where you can grow, change, and share the real stuff, you’re probably going to have to rock the boat. It might be uncomfortable, but it won’t be uncomfortable forever. On the other side, I think you’ll find the work was worth it. In this episode you’ll hear about:The assumption that friendships should always feel good and seamless, with zero challenges as we all move through life’s transitionsDifferent types of work involved in maintaining friendships (and why avoidance is even work, from suppressing urges to withholding details about our lives)Why having those difficult conversations sometimes will not feel good but are important in addressing changes, building resilience, and maintaining connectionHow we feel having hard conversations with partners, family, long-term friendships and new friends; does the label of the relationship impact your investment of effort?Resources & LinksListen to Episode 99 about individualism in friendship with James Richardson; Episode 149 about why we should want our friends to have robust social lives; Episode 153 about friendship break-ups with Meenadchi; and Episode 159 about speed dating for friends.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

Imagine you’re fresh out of college and just moved back to your hometown. Suddenly, making plans with your friends feels hard.Instead of meeting them in the apartment next door or in the dining hall, you’re texting back and forth, trying to get together – but much of the time, it doesn’t pan out, or it’s just not the same. This story is a reality for so many people, including today’s guest.Jason Edmonds is a Seattle resident who decided to make his own solution: Six Degrees, an event-based social experience that matches people through personality quizzes and groups them into activities, helping people in Seattle find their people. In this interview, we talk about vulnerability. We talk about Six Degrees. We talk about the stigma of getting help to find friends. Most of all, we talk about how common this whole experience is. Transitioning from college to adult friendships is hard, and many of us could use a little extra help.In this episode you’ll hear about:The common experience of post-college friendship struggles: in college, socializing was so easy, but as adults it’s more complexSix Degrees, an event-based social experience designed to help people find new friends through intentional activities and personality quizzesThe difference between college and adult friendships and the importance of vulnerability and intentionality in friendshipsUsing social media and technology as a bridge when you meet someone at a meet-up like Six DegreesResources & LinksFollow Six Degrees on Instagram.Listen to Episode 21, which is about that shift in friendship during our mid- to late-20s; Episode 41, about the Liking Gap; Episode 123, about maintaining friendships without proximity; and Episode 145, about reframing rejection. Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!