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 teenager
• The value in being specific when asking someone to hang out and suggesting an activity or time
• The 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 are
• How to make it easier to ask somebody to hang out by choosing an activity they’re already partaking in

Resources & Links

Listen 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 group
• How Alison used Instagram as a kind of “friendship dating app” to find and connect with people in her community
• Real Time Creator, which documents Alison’s career break from being a high-earning breadwinner to taking a creative sabbatical
• Alison’s challenge to have coffee with 10 new people over the course of a year, and her experience organizing low-stakes hangouts

Resources & Links

Find 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 windows
• In 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 & Links

Listen 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!