How 10 Coffee Dates Changed Her Friendships

Friendship IRL podcast promotional graphic for Episode 166. The top half features a muted teal background with a photo of guest Alison Kinsey, a woman with long red hair and blue eyes wearing a dark floral dress, credited as "@ALISONKINSEY." Curved white text in the upper left reads "Episode #166." The bottom half has a cream background with dark text reading "HOW TO" and bold burnt orange text reading "INVITE NEW FRIENDS FOR COFFEE," above the Friendship IRL logo.

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What if I told you that 10 hours… just 10 intentional coffee dates spread across a year… could completely rewrite your story about friendship?

Not 60 hours. Not 200 hours. Ten.

Alison Kinsey is living proof. For most of her life, she was the shy, awkward kid with one friend. The girl with her nose stuck in a book who never wanted to be seen. Fast forward to today, and she describes her superpower as “building intentional community and curating meaningful friendships.” She organizes events. She reaches out for coffee dates. She brings people together.

But here’s what makes Alison’s story different: she didn’t just wake up one day as a connector. She made small, intentional choices over time that slowly shifted how she saw herself. And in 2025, she set a goal that seemed almost laughably simple—10 coffee dates with interesting people she wanted to know better. That’s it. Ten hours out of 8,760 hours in a year.

The result? She now walks into community events and sees familiar faces. She’s built genuine friendships. She’s created low-stakes hangout groups that other women are excited to attend. And most importantly, she stopped believing the story that she’s “not good at making friends.”

If you’ve been telling yourself a similar story—that you’re too shy, too awkward, too introverted, too ANYTHING to build the connections you want—this episode is for you.


The Myth That’s Keeping You Stuck

You’ve probably heard the stats. It takes 60 hours to make a friend. 200 hours to make a close friend. And if you’re someone who already feels like you’re drowning in responsibilities, those numbers can feel paralyzing.

Alison felt that way, too. After moving back to New Hampshire in 2019, she found herself in one of the loneliest chapters of her life. She’d just started a high-intensity tech sales job that consumed 90% of her energy. By the end of the day, her tank was empty. She had nothing left to give to friendships. Career was getting all her attention. Community was getting maybe 1%.

She knew something had to change. But the idea of spending 60 or 200 hours building friendships? That felt impossible.

So she asked herself a different question: What if I just started somewhere?

In January 2025, she made a list of 15 interesting people she wanted to meet. She reached out with simple, casual messages: “I think you seem really awesome. I think we would connect. Let’s get together.” Out of everyone she contacted, only ONE person said no (and only because their calendar was crazy).

By the end of the year, she’d completed 10 coffee dates. Just 10 hours. And those 10 hours changed everything.

Listen to the full episode to hear exactly how Alison structured these coffee dates and what made them so effective.


How Instagram Became Her Friend-Finding Tool

Before Alison started reaching out for coffee dates, she did something most people don’t think to do: she went “psycho following people” on Instagram.

Her words, not mine.

But here’s what makes her strategy so smart—she wasn’t just randomly following accounts. She was looking for people who were INTEGRATED in her community. People who posted pictures at local coffee shops. People who showed up at local events. People who seemed open to connection.

“To me, Instagram is like a dating app for friends, even though it’s not really built that way,” Alison told me.

She’d look at geo-tagged locations for local businesses and coworking spaces. She’d scroll through follower lists and comment sections. She’d click on hundreds of profiles, looking for people who seemed interesting. And then she’d start engaging—likes, comments, just showing up in their world a little bit.

This wasn’t about building an online presence. It was about RESEARCH. She was figuring out who was already showing up in the rooms she wanted to be in. And then she made it a point to actually meet them.

What I love about this approach: Alison wasn’t waiting for the perfect moment or the perfect person to magically appear in her life. She was actively seeking out people who aligned with what she was looking for. And she was doing it in a way that felt low-pressure and genuine.

If you’re someone who’s been waiting for friendships to just happen, this is your permission to stop waiting. Start seeking.


The Power of Talking to the Connector

When Alison first moved to San Diego years ago, she joined a Meetup group for couples in their 20s and 30s. But instead of just showing up at events and hoping to click with someone, she did something bold: she reached out directly to the organizer.

“Rather than just joining different networking groups and getting into those rooms, I said to myself, I’m going to go talk to the organizer of this meetup and see if we connect,” Alison explained.

She and her husband scheduled a blind double-date happy hour at a Mexican restaurant with the organizer and her partner. They completely hit it off. And suddenly, getting into the events felt so much easier. She already knew someone. That person could introduce her to others. It created a domino effect.

Here’s the takeaway: Look for the connector in the room. The person who naturally brings people together. The one who’s organizing the events or starting the conversations. Connect with THAT person.

And here’s the thing—connectors LIKE connecting. I’m a connector myself, and I get genuine joy not just from meeting people, but from introducing people to each other. So don’t feel weird about being a little shameless in seeking out that person. They’re probably thrilled you reached out.

The full episode dives deeper into how Alison built lasting friendships from that one Meetup group—friendships that continued even after she moved across the country.


When You Have to Start Over (Again)

After seven years in San Diego, Alison and her husband moved back to New Hampshire. They wanted to be closer to family. They wanted to plant roots. But starting over felt HARD.

For a long time, Alison had one foot in New Hampshire and one foot in San Diego. She wasn’t ready to let go of the community she’d built. Within six months of moving back, she took a six-week trip to San Diego because she just couldn’t fully commit to her new life.

“I realized, okay, I can’t do this. I can’t be spending all this money. I can’t be leaving my husband for six weeks. I knew I needed to rebuild,” she said.

And then the pandemic hit. In December 2019, they moved into an apartment in a cute coastal town in New Hampshire. By early 2020, everything shut down. She was stuck at home, working a high-pressure sales job, pouring all her extroverted energy into work. By the end of the day, she had nothing left for friends.

It was one of the loneliest chapters of her life.

But here’s what I want you to notice: Even in that loneliness, even when it felt impossible, Alison didn’t give up. She just waited for the right moment to act. And when she finally did, she started small.


The 10 Coffee Date Experiment

In January 2025, Alison decided to try something simple. She made a list of 15 people she wanted to meet. She reached out with casual messages. And she committed to 10 coffee dates over the course of the year.

That’s it. No grand plan. No huge time commitment. Just 10 hours.

“I realized, like, I need to be really intentional about this,” she said. “And so I started reaching out to people. And out of everyone I reached out to, only one person said no.”

She met up with people at local coffee shops, usually right before work. And the first thing she noticed? How ENERGIZED she felt for the rest of the day. Any day she had a coffee date, it changed the whole tone of her day.

But beyond the immediate boost, something bigger was happening. She was learning things about people she didn’t know from looking at their Instagram. She was building connections that made community events feel less intimidating. She was seeing familiar faces in rooms where she used to feel like an outsider.

And some of those coffee dates turned into repeat hangouts. Into actual friendships.

Here’s what Alison wants you to know: It’s not that 10 coffee dates created some life-changing, crazy impact. But it was an impact that CONTINUED to pay off. Because now she goes into rooms and sees people she knows. She has threads of connection she can pull on. She has friendships that are growing.

“You don’t need the big number. You just need to start somewhere.”


How to Invite Someone (So They Actually Say Yes)

One of the biggest fears people have about reaching out is being rejected. Or worse, they’ll get a polite “yes” that turns into a flaky “sorry, I can’t make it” later.

Alison’s approach? Keep it simple. Keep it genuine. And don’t make it transactional.

When she reached out to people for coffee dates, she’d send a quick DM or email: “I think you seem really awesome. I think we would connect. Let’s get together.”

That’s it. No agenda. No hidden motive. Just genuine curiosity.

And here’s what’s interesting—only ONE person at the end of a coffee date asked her, “So what can I do for you?” And Alison’s response? “I really don’t have anything. I genuinely asked you here to connect.

This is so important. People can FEEL when you’re being transactional. When you’re only reaching out because you want something from them. But when you approach connection from a place of genuine curiosity? People are WAY more likely to say yes.

In the full episode, Alison breaks down exactly how she structures these coffee dates and what makes them feel low-pressure for everyone involved.


Creating the Spaces You Wish Existed

Alison didn’t just wait for the perfect friend group to appear. She created it.

In New Hampshire, she started a group called “Business and Friendship” for women who are building something. Entrepreneurs. Creatives. Business owners. But the goal was never just networking. The goal was FRIENDSHIP.

She organized a business book swap where everyone brought their favorite nonfiction book and talked about how it impacted them. She hosted a pumpkin flower-pressing event. She invited women to a vision board night at her house with wine and snacks.

All low-stakes. All easy to attend. All focused on connection first.

“I truly believe that if the thing you want to join doesn’t exist, create it. Just create the thing and just take the initiative and do it.”

And here’s the ripple effect: One of the women at the pumpkin event invited Alison to learn how to play mahjong with some other women. Another coffee date led to a LinkedIn shoutout that resulted in three more virtual coffee dates with women across the country.

Small actions. Big ripples.


Why Smaller Is Better

One of Alison’s core principles? Keep gatherings small. Eight people or less.

“I feel like eight or less is just a perfect number so that you can truly get to know every single person in the room,” she explained.

And I think this is SO important. When you’re trying to build genuine connections, bigger isn’t always better. Bigger can actually make it harder to go deep. Harder to feel like you really connected with anyone.

Small gatherings let you have real conversations. They let you learn something meaningful about each person. They make it easier to follow up later because you actually REMEMBER who was there and what you talked about.

If you’ve been avoiding hosting because you feel like you need to invite everyone, this is your permission to keep it small. Invite the people you genuinely want to get to know better. Create space for actual connection.


The Identity Shift That Changes Everything

At the beginning of this episode, I told you that Alison used to be the shy, awkward kid who never wanted to be seen. The girl with one friend. The one who always had her nose stuck in a book.

Now she identifies as a connector. A community builder. Someone whose superpower is bringing people together.

That shift didn’t happen overnight. It happened through small, consistent actions over time. Through showing up even when it felt uncomfortable. Through reaching out even when she wasn’t sure people would say yes.

“I really, truly believe that all of these conversations and connections, they will pay off,” Alison said.

And she’s right. They do.

But here’s the thing: The transformation isn’t just about making more friends. It’s about changing how you SEE YOURSELF. It’s about rewriting the story you’ve been telling yourself about who you are and what you’re capable of.

If you’ve been telling yourself that you’re bad at friendship, or you’re too shy, or you’re just not that person—I want you to hear this. That story is not permanent. You can rewrite it.

It might not happen in a month. It might not even happen in a year. But if you keep showing up, keep putting yourself out there in small ways, keep taking small actions, one day you’ll look back and realize you’re not the same person anymore.


Alison’s Advice for Your Past Self

At the end of our conversation, I asked Alison what she would say to herself 20 years ago. To the version of herself she no longer identifies with.

Her answer? “I would tell her to stop caring what other people think. There’s always a reason for that fear of being seen and being visible, and there was a lot of insecurity rooted underneath that. So I would tell her to stop caring what people think. Put yourself out there. Raise your hand. Be confident.”

And that’s exactly what she’s doing now.

She’s putting herself out there in bigger ways than ever before. She started her own podcast called Real Time Creator, where she’s documenting her career break and creative sabbatical in real time. Every week, she’s sharing the identity shifts, the big decisions, the messy middle of choosing herself even when it doesn’t make sense.

If you’re someone who’s been craving a pivot, or you’ve been laid off and just want to feel less alone, go check out her podcast. I’ve linked it in the show notes.


Your Turn: Can You Commit to 10 Hours?

So here’s my challenge for you. Can you commit to 10 hours this year? Ten coffee dates. Ten intentional conversations. Ten small actions that could completely shift how you see yourself.

You don’t need 60 hours. You don’t need 200 hours. You just need to start somewhere.

Make a list of 15 people you’d like to know better. Follow some accounts on Instagram of people who are showing up in your community. Reach out with a simple message: “I think you seem really awesome. Want to grab coffee?”

And if that feels too scary, remember what Alison said: Put on an alter ego. Give yourself a stage name. Embody the up-leveled version of you that IS confident, that DOES reach out, that ISN’T afraid.

Because here’s the truth: The story you’ve been telling yourself about friendship? It’s just a story. And you can rewrite it.

Listen to the full episode for even more insights from Alison about rewriting your connection story and building the community you’ve been craving.

Resources Mentioned

Find Alison Here:

Related Friendship IRL Episodes:

  • ▪️ Episode 12: Digging into the Roots of Connection
  • ▪️ Episode 14: How a Group of Friends Is Actually Made Up of Individual Relationships
  • ▪️ Episode 44: How Making Friends Can Help You Make the Big Life Choices with Daesha Waddup
  • ▪️ Episode 48: Actionable Ways to Build the Connections You Need in Your Community with Michele Reichman
  • ▪️ Episode 83: The Case For Making Friends Who Are In Different Life Stages Than You
  • ▪️ Episode 100: Celebrating 100 Episodes – Plus, an Extensive Look at the Wheel of Connection
  • ▪️ Episode 134: All About Fringe Friends

Book Mentioned:

  • ▪️ The Big Leap – Book about breaking through your own glass ceilings

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Hi. I'm Alex.

I’m obsessed with helping people build the support systems they actually need. Through my book, podcast, and community, I share the frameworks that transformed my life from lonely and overwhelmed to deeply supported.

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Hi. I'm Alex.

I believe everyone deserves a support system that actually holds them.

Friends to call after a rough day, emergency contacts, a neighbor who will grab your mail – I teach you how to create it all.

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