20 Questions to Ask Your Friends

If you were on death row, and were about to eat your last meal, what would you want to eat?

Follow-up: Why would you be on death row?

How do you give and receive love?

What are you asking God for?

What are words that you want to be true of you?

Follow-up: What needs to change for that to be true?

What’s saving your life right now?

How do you know that I really love you?

How do you most experience God? (In community, in worship, in nature, etc.)

What are five things that are always in your fridge?

What’s one of your favorites? (Favorite anything.)

If you won the lottery, what’s the first place you would shop?

Next year looks better because…

I’m most like my mom/dad because…

What’s the best news you’ve heard this week?

If you would have one meal with any person dead or alive, who would it be?

What did you want to be when you grew up?

What would you super power be?

I want to be taken more serious in the following area…

What do you dream of doing?

What would your best friend say about you?

What’s a great story that best defines who you are or who you want to be?

Vacationing With Your Friends

I come by my love of both friendship and vacation honestly. Growing up overseas in a tight-knit expat community, almost every vacation we took were taken with other families. Not only did we vacation together, but we went to school with and lived in the same apartment building as most of my parents’ best friends. In a 31 floor apartment building, we didn’t have to travel far to spend time with one another.

In so many ways, it was like being in college, with late nights and the intimate friendships that you can only build when you see each other multiple times a week and often without make-up on. Once you add in the way that a shared expat experience bonds families together because you literally don’t have anyone else to lean on, my friendship expectations were doomed to be unrealistic.

But truly one of my favorite parts of living in Japan was traveling with other families. I cannot remember my family’s time in Malaysia, Indonesia, Guam or Saipan without remember the other families who we traveled with. The people who brought my family meals after my dad’s open heart surgery were our “Japan Friends.” Traveling with others does something special to a friendship that can rarely be replicated in real life. It creates a bond that’s stronger than you dreamed it could be. 

I saw this happen with my family’s friends, but I’ve also seen it happen with my friends.

Two years out of college, a group of us invited quite a few friends who we knew from school on a week long vacation. That first year, eleven people stayed in a Florida beach house as we started a new tradition.

We had themed dinners, dance parties in the kitchen, wore our matching t-shirts, had a star contest and made sure we were all tagging our photos with a pre-determined hashtag. But, more important were the conversations around the breakfast table and the sharing that happened at our Monday morning “Family Time” where each person talked about what they were walking through, and we prayed for them individually.

Friendcation, as it’s come to be known, has truly changed us. There’s no escaping each other now, we’ve vacationed together. We know what happens when someone doesn’t get enough sleep, who is most likely to get sunburnt on the first day (me!), and who makes sure the coffee pot never stops brewing coffee in the morning. There’s a true vulnerability is sharing a house with friends for a whole week. 

You can bring your best self to a weekend getaway, but it’s harder to fake it for a whole week. Vacation removes the filters of busyness, social media and the comfort of home. You have no choice but to be authentic around people who you’re sharing a kitchen and bathroom with. 

Our vacationing together has given us the gift of being known not just who we were in college, or who we are right now, but who we hope to become. It’s so special to have these friends know me so intimately that they call me to be a better person when I forget what I’m working towards. They anchor me in who I am and remind me who I hope to become. They bear witness to my life. 


Favorite Podcasts on Friendship

I like listening to podcasts almost as much as I love reading! I listen to podcasts with subjects similar to what I read – story-based non-fiction, news related, and faith-based stuff. Over the years that I’ve been listening to podcasts, I’ve got some favorites, especially related to friendship. Each one is a little bit different. Some tell stories of friendship, where others can give instructions for how to make a friend or what friendship can look like. If you’re anything like me, and love learning about and seeing friendship, you should take a listen to these podcasts!

Sorta Awesome, episode 54, Ten Friends Every Woman Needs is one that I recommend most frequently. There’s a myth in our culture that you need a best friend. A singular best friend who meets all your needs. Depending on your season of life, that “best friend” is going to look a little differently. This podcast episode challenged the best friend myth, and reminded me of the importance of having a diversity of friends. Not even just a close knit friend group, but friends who meet a variety of needs, and who may not even know each other.

For The Love with Jen Hatmaker, episode 3, Girlfriends Can Save the World with Shasta Nelson, reminded me why I think friendship is not just important, but vital for our lives. Shasta has done significant research on how to develop intimate friendships and what happens when we don’t have them. I’ve since picked up her book, Frientimacy, because of how much I loved listening to her talk on the podcast. Chances are, if you’ve seen me since August, I haven’t been able to shut up about how destructive loneliness is, and that’s a topic I learned all about on this podcast. I’m more committed than ever to be a person who saves my friends from loneliness.

For The Love with Jen Hatmaker, episode 5, Real Girlfriend Stories from the Tribe brought me to tears. For The Love is a podcast that my best friend and I both listen to, and after we both listened to this episode, we started crying talking about it to one another. It’s a real story of what blood and guts friendship looks like. After listening to it, I wanted to be a better friend – to love deeper and more sacrificially for the people I’m closest to.

Happy Hour #144 with Sarah Harmeyer was one of my favorite episodes of the Happy Hour with Jamie Ivey, and I’ve listened to almost all of them. I highly recommend the Happy Hour in general because it’s always good; even the episodes that I’m less interested in are GREAT! This episode was a special one for me because of the concept of The Neighbor’s Table that Sarah Harmeyer introduced and how she’s lived out community in her own life.

I’d love to hear what podcast recommendations you have on friendship and your favorite topics! I’m always looking to learn and listen to stories while I run or drive.

Personalities & Friendship

I can quite get enough of personality tests. I’m obsessed. I could talk about Enneagram and Myers Briggs until I’m blue in the face. Chances are, I’ve tried to figure out your Myers Briggs letters in our first couple interactions.

There has been a lot of research done about the role that our personalities play in our relationships – romantic and otherwise. Smart people have all types of theories about which types are most compatible.

I believe that personality tests have their place in helping us understand ourselves. I wouldn’t be obsessed with them if I didn’t. Knowing my personality type (ENFP & Ennegram 7) has helped me better know how I’m wired, and why I respond the way I do to certain situations. But, I also think we can use our personality to let us off the hook for developing meaningful relationships.

Introverts need companionship just as much as extroverts do. Humans are relational beings, and desire interaction with others. An introvert may leave a social gathering tired and in need of alone time, but that does not mean that he should avoid attending parties. It simply means that he needs to be aware of how he recharges — alone time — and plan accordingly.

Extroverts should also be cognizant of how much time they spend with others. Quality time to connect with friends is not the same as spending a lot of time with them. While the temptation may be to have all your favorite people in one place — I speak from personal experience — having them all in one room doesn’t mean that you’ve actually deepened the relationship. It may serve an extrovert’s friendships better to devote time to coffee dates or smaller gatherings.

Personality types can be key in self-development, but they should never be an excuse for unintentional relationships.

We have to be so careful that we don’t allow our personality type or even our preferences prevent us from making new friends and deepening existing friendships.

How to Make the Most of Living With Roommates

I’ve lived with over a hundred women. No, I’m not the worst roommate who sends others running for the hills, nor do I move frequently. I’m actually a fairly normal twenty-something. I lived with one hundred other female students in a sorority house for two years in college, and then shared a picturesque college town house with four of the same sorority sisters. I then moved into an apartment with two roommates right after I graduated. They were both engaged within a year, so two new women moved in. I now live in an adorable bungalow with three other friends.  

My roommates have seen a side of me that few other friends have seen. They know that my purple fleece pants are my favorite item of clothing for laying on the couch, that I’d rather not speak to anyone until at least nine in the morning, that I don’t love to work-out with other people and that nothing sounds better to me after going to the gym than eating Chick Fil-A.

I’m far from a perfect roommate. I’m pretty messy, I am a verbal processor, I can keep weird hours and I covet alone time, but I like to think that I’ve learned some important lessons along the way. While others have worked towards living alone, I’ve grown to see the benefits of living with others.

Choose When to Speak Up

I currently live with three other girls. While we care about each other, one small annoyance about Roommate A expressed to Roommate B can turn ugly quickly. Unfortunately, that’s the nature of gossip. Some annoyances are good to speak up about, but others will be quickly forgotten. It’s important to know the difference. When I’m frustrated it helps to remind myself that if I don’t want to confront a roommate about something directly, then I need to drop it and move on. 

Learn What Each Roommate Values

I spent months worrying that the messy bathroom upset my roommate, but did not think twice about leaving my cereal bowl in the sink. Then after asking her, I found out that the dirty bathroom didn’t bother her, but keeping the kitchen clean was of the highest importance. It’s been a win, win situation because I can focus my efforts on what matters most to her, and worry less about toothpaste residue in the sink.  

Learning what a roommate values goes beyond knowing that she likes a clean kitchen. Like you would with a good friend, seek to learn what your roommates like after a hard day at the office – coming home to quiet or going out for dinner. Nothing shuts me down quicker than voicing my frustrations and a roommate responding with advice. When I’m frustrated, I don’t want someone telling me what to do; I either want empathy or silence. Getting to know your roommates, asking intentional questions and observing their reactions to different situations will help you better care for them.

Communicate Your Expectations

Home should be a safe space; a place where your needs are met, and where you can experience rest. This cannot happen unless you are open with your roommates about personal space, cleanliness standards and boundaries when it comes to sharing food. Some roommates set ground rules at the beginning of living together to clearly set out rules or expectations. Depending on your home’s need for structure, it may be helpful to write out these rules and post them in a public place.

The following topics should be discussed either leading up to moving in together or in the first month: overnight visitors, noise levels, cleaning responsibilities and paying bills.

Ask For Forgiveness

You will inevitably break a wine glass, shrink a favorite shirt, forget to take the trash out or hurt a roommate’s feelings. Believe me, I’ve done all of the above. Be quick to apologize. Some apologies are easier than others. Our homes are where we are able to live out grace, to apologize and to forgive. If you learn to practice forgiveness with those closest to you, this practice will follow into other areas of your life.

Seek To Out Love One Another

It’s human nature to want to make household responsibilities fair. In every living situation I’ve been in, during a hard week, someone starts keeping score. It sounds something like this:

 “I’ve taken the trash out the past four weeks.”

“No one else ever empties the dishwasher.”

“Roommate A always leaves her dirty dishes on the coffee table.”

Full disclosure: that someone who keeps score is often me. Unless your roommate is the worst, chances are, he or she is doing things that you are unaware of. No one wins when you keep score. Instead, make it your goal to serve more, love bigger.  Like forgiveness, servant-heartedness will follow you into your office and into your church.

If enjoying the roommate experience sounds a lot like being a good friend, that’s because it is! Hopefully you like spending time with the person who you are living with so it is fun, and you are able to build a friendship. Whether it’s a short-term or long-term experience, living with a roommate can be a great experience when you adopt the correct attitude and desire to make the most of it.


Last spring, I messed up pretty publicly. It was the kind of mess up that you you wake up the next morning full of conviction and maybe even some shame. It didn’t help that it was at a wedding with so many of my college friends. Everyone saw me in one of my lowest moments. I was a train wreck that no one could look away from.

I spent the whole next day crying because I was embarrassed, and sad. I had no one to blame but myself. This mess up was something that used to be a pattern in my life, but I thought that I had moved past it. Truly, it rattled me to my core.

I remember the conversations in the couple of days after this public mess-up. I called my best friend, apologized for my behavior and asked her who else I needed to apologize to. I confessed to my roommates what I had done. It was almost as if I wanted everyone to know what happened so I could move on and forget it. I continued to be shocked by the responses of each of my close friends.

In my self-condemnation haze, I couldn’t remember what was true of me. I felt as though I was a sum total of the mess-up.

Yet with each person, I was met with grace.

Grace that I didn’t feel worthy of because of my mess-up. Grace that acknowledged what I did was wrong, but didn’t permit me to continue on in my shame. Grace that restored me back to what’s true of my identity.

One of my roommates spoke the sweetest words over me as I shared what I did and how I was feeling about it. Standing in my kitchen, she said, “Caitlin, God is pleased that you confessed this to Him. You are forgiven already. He just wanted you to come to Him.”

I’ve mostly broken myself of my perfectionist tendencies. But every once in a while they rear their ugly head. Usually it’s when I mess up. I often live my life in a way that says I believe that grace gets me 99% of the way to the finish line, but the last 1% is all me. So when I mess up, I cannot finish. I failed. My mistakes, especially the public ones, can damage my heart on a deep level.

Thankfully, I have incredible friends who continue to be my friend even when I mess-up, and restore me back to my right place. When I feel defined by my behavior, they remind that my identity is much deeper than one night’s mistake.

But the restoration can only come when we’re aware that we need to be restored, and when we ask for it. When I’ve felt the most disappointed in friendships, it’s when I’ve been the least vulnerable. Thankfully, last spring when I needed my friends to remind me of who I was, I was open enough to confess the mistake so that they could be part of the restoring.

Grace is freely available, but you do have to ask for it. Friendship can be part of the restoration process, but you do have to be open about your need.

Friends Who Shift Our Focus

Each summer, some of my college friends spend a weekend at a lake in Northern Indiana. It’s come to be known as Lake Weekend, and usually falls towards the end of the summer. Each year it’s a blast, and an amazing time to reconnect with people I only see a couple of times a year and a good change of scenery even for friends I see on a day-to-day basis.

As with any tradition, the first year we had the smallest group. There were nine of us in this beautiful lake house for the weekend. I was almost a year into my job, one full year out of college, and still wrestling with my life not looking like I wanted it to look. There were some periods where I was working thirteen days in a row, both my roommates were either engaged or almost engaged, and it felt like everyone else had things figured out. I walked into the weekend pretty drained. Worse, I didn’t have hope that things were going to get better.

Saturday night after dinner, all nine of us jumped on one of the boats. All it took was one question, “How are you doing?” to begin a time of sharing. I’m usually the first to share. I like to set the tone, and I’m a verbal processor, so no matter how much time I have to think about something, it will usually come out the same way. But this night was different. In the midst of all of my friends who seemed to be thriving, I didn’t want to be the one who was uncertain.

When it was finally my turn to share, I’m sure I fumbled through an answer about how discontent I felt at my job. I remember saying something about how I wasn’t experiencing joy regularly, too. In my mind, these two things were inner-connected. Being unhappy at my job was clearly preventing me from experiencing joy in my life. A friend responded with a question that shifted everything. He asked, “Caitlin, when have you experienced joy in the past year?”

I probably answered something in the moment about community, but the question triggered more than an immediate response. That next week, I went home and wrote down all the things that brought me joy. Reading, writing, cooking, running, and throwing parties all made their way onto the list.

I took that list and looked critically at my weekly schedule. Even though I was working almost sixty hours a week between both of my jobs, I tried to incorporate some of these joy-giving activities into my weekly schedule.

At my healthiest, I’m a big picture kind of girl. I dream, I plan, I create. But, when I’m overwhelmed, I get tunnel vision, and can’t seem to see past the struggle of the day. The simple question asked by a friend, was the act of lifting my chin. It forced my eyes from my feet to the road in front of me.

Even more than shifting my gaze, my friend’s question helped me see my life more holistically. I could still struggle with feeling unfulfilled at my job, but experience joy in relationships, through reading books and trying new recipes.

That was three years ago. We’ve returned to the lake three more time since then. Of that original nine people, three have gotten married (two to each other), we’ve welcomed two babies, celebrated two graduations, with one more to come, bought two houses and a lot of us have gotten new jobs. Today I love my job, truly, even though I’ve gone through seasons more recently when I haven’t. But I’ll always come back to that simple question asked by a dear friend as defining moment that changed me. 

Friendship has this unique ability to force us to see beyond what’s right in front of us. Community allows us to dream bigger, create better and live more fulfilled lives, if we let it.


My Favorite Books on Friendship

I’m an avid reader. I do read more in some seasons and less in others, but if you see me with a book, it’s most likely a non-fiction book. I love real life stuff. No escapism here in my reading material… only in my Grey’s Anatomy watching. So, in honor of my month on friendship, I’ve decided to share with you my favorite books on the topic.

All of Shauna Niequist’s books have essays about friendship. I really could have picked any of them as a favorite book, too. But, Bread and Wine is the most fitting because it’s her love letter to life around the table, and for Shauna, the table is where she meets with her people. The book contains recipes, stories and practical application for how to build community. I was encouraged to love better and live more authentically after reading Bread and Wine. (If you’re looking for another book by Shauna Niequist about friendship, both Bittersweet and Present Over Perfect are must-reads. Both are full of essays that challenged me into deeper relationships with those closest to me.)

Living into Community by Christine Pohl was an important read for me last year. The author focuses most of the book on four practices to cultivate and live into community. Gratefulness, promise keeping, truthfulness and hospitality are the four practices that Pohl highlights. This book is a true gift because of it’s deeply biblically based ideas and practical application points. A year after reading the book, I’m still struck with the idea of Jesus giving thanks in the context of community, and how grace is tied to gratefulness.

Deepening Community by Paul Born is a timely book about finding joy together. It’s a secular view of how community is formed and deepened. Born’s look at community examines how people develop a sense of belonging to one another, starting with a shared story and eventually joining together towards a common purpose. His work and stories challenged me to think about how my own friendships could be deepened, namely, what narrative do we share with one another, and what are we working towards as friends.

Frientimacy by Shasta Nelson is a recent favorite book on friendship. I “met” the author on a podcast and I couldn’t stop thinking about the way she talked about intimacy, specifically intimacy in friendship. She talks about how loneliness is an epidemic facing our culture today, and that in fixing loneliness (through friendship), we see our overall health improve. She has a very fascinating question that she asks women, and I’ve started asking my own friends, “On a scale from one to ten, how lonely are you?” It’s helped me better understand how I can be a better friend and what their needs are.

No list of friendship books would be complete without Dietrich Bonhoeffer’s Life Together. This short book packs endless wisdom and biblical truth into about 100 pages. Much like Paul’s letters written to churches who were experiencing suffering, Bonhoeffer gets right to the point in the very beginning of his friendship narrative by saying, “It is not simply to be taken for granted that the Christian has the privilege of living among other Christians.” He goes on to say, “It is grace, nothing but grace that we are allowed to live in community with Christian brethren.” Bonhoeffer lived in a time when the cost of following Christ was especially high. In times of oppression, the importance of Christian fellowship is heightened.

Friendship & Singleness

I’m twenty-six years old and unmarried. In Christian circles, my empty left ring finger and I stand out, and even if we’re not noticed right away, we usually make ourselves known in the first couple minutes of a conversation. I’ve mastered the question progression. It usually sounds something like this:

“What do you do?”

“Do you have kids?”

“Are you married?”

We’re working through it, my empty ring finger and I. We’re trying to let our guard down quicker, and be vulnerable even when we wish we could just stand there are talk all about where our kids go to school. Some days are easier than others. Some seasons are easier than others. But I also know that God is only good, and can use my experience in the lives of others.

And He truly has. Last fall, I wrote significantly on being single. Even just reading the words now brings tears to my eyes. I felt so hopeless that I could feel a part of community or that I would be seen as someone who had something to bring to the table. In the past year, I’ve watched God use my loneliness to comfort others. I’ve watched God use my free time to enable me to pour into the lives of others. I’ve watched God put me in places where my unique experience has been valued.

But, I still think the application points I shared last fall about living life alongside others who in other seasons of life is vital. When Jesus called us to live in community with one another, and when we look at how the early church lived, it’s clear they didn’t segregate themselves by season of life.

Here are some starting points:

  • Reach out to someone who is in a different stage of life than you. Maybe before you reach out to them, say a prayer and ask God to share with you some truth about them that you can pass on. Maybe it sounds like this, “God put you on my heart this morning, and whatever you’re walking through, remember, He hasn’t forgotten you. He sees you, knows you, and loves you.”
  • Enter into the celebration and the mourning. It feels like a non brainer that when a spouse is out of town, the other spouse needs help with the kids, and may need help with meals. But traveling is hard on singles, too. So is loss. Remember birthdays and anniversaries, if you can remember to send a card, even better. Celebrate promotions and steps of faith. Communicate your needs to people so they know how they can come alongside you. Keep showing up.
  • When you ask questions of someone, ask about them as an individual. Don’t ask first about their kids or their spouse, begin with them. How are they doing? What are they feeling? How can you be praying for them?
  • Start by being vulnerable in your own responses. If the real answer to the question of how you’re doing is lonely, say it. I think you’ll find that your vulnerability, however painful, gives someone else the gift being vulnerable, too. If you’re the mom or the wife, avoid making how you’re doing about someone else. I want to hear about your kids, but I asked about you. Let’s start there. It’s discouraging to a single person when they’re vulnerable on a heart level and it’s met with an anecdote about your child.
  • Be unafraid of the awkwardness. I’d rather be a fifth wheel a hundred times than not be invited because of how it may make me feel. And I think my married friends would say that they’d rather be invited knowing they’d be the only married couple in the room than be excluded. Keep inviting the new parents; let them decide for themselves if they can come.

Did I miss some important stuff? Probably. So I’d love to hear where your starting points are. Maybe you’re not single, but you’re the first married couple in your friend group; how do you feel cared for and included? Maybe you have been well cared for by friends in a different season of life. What has that looked like?

The stakes are too high for us to keep getting this wrong. Let’s lean in, friends. Let’s shoulder this kingdom responsibility side by side regardless of if there’s a ring on your left hand.

Jesus & Peter

Redemption. It may be one of my favorite parts of being a follower of Christ. I know it’s definitely one of the things that gives me hope. As a Christian, I firmly believe nothing is too bad to be forgiven. Nothing.

We get a picture of this in Jesus’ resurrection from the dead, but also in how He interacts with Peter.

Let me introduce you to Peter. When we first meet him, he’s catching fish. Then Peter meets Jesus, and Peter immediately begins to follow Him. He’s pretty impulsive, Peter. Throughout Jesus’ ministry, Peter seems to get himself in trouble by opening his mouth and at times failing to see the bigger picture. (Are you realizing why Peter is my favorite?)

At the end of Jesus’ life, after traveling around with him, and being part of his inner circle for years, Peter betrays Jesus. In fulfillment of prophesy. But also because he’s afraid. Most times we hurt people, it’s out of fear, right?

So Jesus dies, rises again, and Peter goes back to fishing. Yes, he returns to his original life. Probably out of shame and uncertainty; he tries to go back to the life he was living before. Even though he know’s there’s a better life for him. At this point, you’re probably wondering why this is a in a series on friendship. Hold on, I’m going to get there.

Jesus, back from the dead, meets Peter and some of the disciples on the shore. Remember Peter was back to being a fisherman. Performing yet another miracle, Jesus provides those on the boat “an amount of fish so great that they couldn’t haul in their nets,” (John 21:6). They head back to land and eat fish with Jesus.

Then Jesus does something special for Peter. He says to Peter, “Peter, do you love me?” Peter responds, “Yes, Lord, you know that I do.” Jesus proceeds to ask the question three more times. Which is the exact number of times that Peter denied Him earlier in the story. In essence, Jesus gives Peter a re-do.

Jesus comes back from the dead, to demonstrate that God has power over the dead, and while He’s at it, He restores Peter to right relationship with Him.

But He doesn’t stop there. Jesus gives Peter a mission to feed His sheep. The subtext in this command is Jesus saying to Peter, “Remember I changed your life? Don’t go back to fishing. I called you to care for my people. So do it!”

There’s a whole lot more going on in this story that I love, and I’ve written about it before, but truly, it’s a story of forgiveness, restoration and redemption through relationship.

Peter has abandoned Jesus. Peter went back to doing what he was doing before.
Jesus comes to Peter right where he’s at, even though it’s in a place of disobedience.

Jesus gives Peter the opportunity to make the situation right again.

Jesus reminds Peter of who he is. Jesus puts Peter back on mission.

Peter went on to be a major player in early Christianity. He is the author of several books in the New Testament including 1 Peter, a letter written to Christian exiles who were experiencing persecution. He was eventually crucified for his faith. His words and life have inspired countless people to persevere in their faith, especially in seasons of oppression. 

All because his friend (and Lord) Jesus called him to something more. More than fishing. Again and again. Even when Peter failed to live up to the calling, and betrayed Him; Jesus restored him.

Jesus calls all to come and follow Him. He invites us all onto His mission in unique ways, specific to who we are. Just like Peter, He promises that by the time He’s done with us, we’ll be different people with a new calling.

This is the power of friendship. To meet people in their darkest moments, to wade into their shame, remind them of who they are, and set them back on mission.