“How does everyone have so many more friends than I do?”

In lonely and dull moments, we have all wondered what happened to our girl clan or bro squad, our couple-friend-groups, our ride-or-dies, and our just-stopping-by-to-say-hey pals.

I remember when I moved to Austin, I geared myself up to feel intensely lonely for the first 3-6 months. As an extrovert, my cup for connection is pretty big. I spent lots of time on the phone and at networking events, but I still hit moments of emotional famine without local friends who knew me well.

After moving to three cities solo in my life, I’ve built a very clear strategy to make connections starting with exactly what to do at social events. Once you get the flow of connection with strangers, it’s easy to enjoy the rest of the event… and these are the ground rules to get there.

1. Just make 1 new connection.

Though the idea of “working a room” seems glamorous, it’s only a natural outcome for people who know most people in the room. When the event is one full of strangers and vague acquaintances, it’s a huge waste of time and energy to try to meet and talk to more than four people in one evening.

If you want connection, you’ll need to connect with a few people, which takes time and attention.

If you can have one deeper conversation, the evening will be a success.

So how do we initiate a deep conversation from an awkward hello?

2. Relieve everyone else by introducing yourself.

If you’re in a standing-around situation (pre-dinner mingling, a house party, a bar), you have 2 options. You can step up to an existing conversation (of two people) and ask if you can join it. Or, you can introduce yourself to a person close to you or to a person who looks interesting to you.

Remember, most people are wondering what to do with their arms and looking around for people they know. Introducing yourself kindly is a welcome relief to most people.

From there, you ask a question.

Don’t pick a dead-end question, okay?

3. Ask about feelings and stories, not facts.

The idea is to start a deeper conversation, not to fill the silence. I still haven’t met the person who likes small talk (everyone hates on them?). No. One. Likes. Small. Talk.

The simple way out is to ask about stories and feelings:

❌ Are you from Austin? ✅ What do you like about Austin?

❌ What do you do? ✅ What’s been the best part of your week/weekend?

❌ Cool hat. ✅ Is there a story behind this cool hat?

If the other person leads with a ‘facts’ question, follow up with a feel/story question. How do they feel about xyz? Or, share your similar connection, but add how you feel about it. “I’m from New York too! I loved the energy.”

Bonus: Let go of needing to throw out lots of info about yourself, unless you have something obvious in common. Build affinity first, so they get that you want to talk to them and aren’t just ‘being nice.’ That’s how you work through that initial awkward wall and get to the good stuff.

4. Don’t miss free information.

People usually give away a lot of free information when they’re talking about feelings and stories rather than facts. Free information is all of the unique details about their world that show what they’re into.

Most people just wait for a piece of free information that directly relates to them.
Don’t do that.

For example, someone could share a fantastic story about finding their cool hat in their grandmother’s dress-up closet in New Orleans, and you go “I’ve been to New Orleans,” instead of picking up the much deeper thread about their relationship with their grandmother. The easy route (sharing facts) will run the conversation into the ground much faster.

If you’re actually paying attention, you can find the free information that leads to real connection: stories and feelings, relationships and dreams.

Bonus: If you listen between the lines of their story, you can pick up what they value or what they’re good at. There is no faster way to build connection and affinity than pointing out those deeper things you notice and asking about them.

For example, when someone tells their story of moving on their own, you could go back to facts about where they live now (boooriiing), or, you could notice that they must have been really brave and determined to take a risk like that (I totally WAS brave, thank you to all of you who said so!).

If you’re not sure, then ask, “What was that like for you?”

The goal is for them to feel seen and interesting, which is the best gift you can give to anyone.

5. Navigate logistics in group settings purposefully.

This last point is for talking to multiple people instead of just one.

• At a table of 8+ people, don’t sit in the middle. It’s tempting to want to be ‘in the middle of things,’ but you’ll end up in the middle of two conversations and struggling to hear either.
• Recognize A-B conversations, when there are two people talking and one or more is just listening. Don’t feel bad about asking the person next to you a question directly and starting your own A-B conversation.
• If there’s a lull in your group, ask a group question. “Who had the most exciting thing happen to them this past week?” “What’s the best advice you’ve heard recently?” etc.

Proximity (not personality) builds familiarity.

You don’t have to bring the biggest personality to a gathering to have the best time. In fact, the more listening you do, the more likely you are to make a lasting connection.

Even if it takes 3 events to find someone you really like, it’s worth the time if you can follow up with that one person and see them again within two weeks.

That’s why it was so easy to make friends in gradeschool and college – we would see someone 15 times before we thought of them as a friend.

My strategy for building community in a new city works for any situation where it’s time to make some new relationships. Ask story/feeling questions, listen, follow up, and get in your reps to grow familiarity.

No matter how awkward you feel, it will be worth the 20 seconds of weird to grow the most important part of sustainable happiness – meaningful relationships.