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Learning to love tough-to-love people.



I'm a writer, author, and online educator who loves helping others build intentional lives through the power of habit and meaningful routines.







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I would love to hear from you about how to love hard-to-love family well…how to love someone with no expectations or feelings of guilt when I feel like I’m “not doing enough” to love them.  
To give context, my relationship with my mom is not the best. There has been a lot of hurt and periods of not engaging with her at all in order for me to set healthy boundaries for myself. I am at the point where I do want a healthy relationship with her, but feel like I am the only one putting in work. Or, when I don’t put in work/time/effort, I feel guilty – like I should be doing MORE to re-build my relationship with her. It all comes back to healthy boundaries & loving out of LOVE instead of out of guilt.  

Some wisdom and encouragement would be life-giving 

Happy Monday! 


Dear M,

When you wrote this email to me, all I could think about was a roommate I had years ago. She wasn’t blood-related to me but we spent a lot of time together and it was expected, throughout the time we lived together, that we would treat one another like family. This was anything but easy. I found myself never being able to predict her moods. One day she would be so kind to me and the next morning she wouldn’t even look at me, scowling as she poured her coffee and went back into her room. I couldn’t figure out what mood I’d be met with. She’d often say unkind things to me, wrapping them with a tone of sarcasm or “oh, don’t get your feelings hurt so easily.”  As a result, I started to avoid the issue. I began avoiding her. I tried to shield myself from her unkind words. I took solace in talking about her with my other roommates, hoping they would commiserate with me and I’d be in the right. 

I’ve learned a ton about talking badly about other people in the last years of my life. I’ve learned it’s not hope-filled and it’s not life-giving. Even if I am angry or want to feel justified, I really have to step back to ask myself: am I making myself or anyone better by saying these things? I think it is important to process wounds and frustrations with other people. The vulnerability in that is important. But if your words function more like missiles than white flags, you may need to look deeper to find what is hurting you so badly and why you are taking it out on another person. 

Things never became perfect with my roommate and I. I really felt like I was justified for a long time when I vented to other people but I can look back and say: my unkind words were no better than her scowls and snarky comments. In that situation, we were no different– I was just saying my words behind a closed door. 

It probably took a good six months for me to confront her. I still remember where we were sitting and how the energy in the room shifted as I started to be honest with her and just tell her that I really didn’t like being around her, not because I didn’t like her but because I was afraid of being hurt. Our conversation was raw and real. We came to agreements. We set up boundaries. We dug deeper and I learned things I would have never known about her if I hadn’t just held my courage and proceeded into a dialogue. That day was a tiny victory in the name of love. I still remember it. 

M, I’m going to speak a little broader about this topic knowing that some people have “tough” roommates and “tough” friends. Some people aren’t at the stage of investing totally in a family. Some people feel a lack of family. I know I still have a long way to go so please take my words lightly. I’m no expert. 

There are just a few things I’ve learned *and am learning about the tough-to-love people (and that definitely includes me as one of them):

Start with what you’ve got.

Guilt is tough to wrestle to the ground. And you’re very right, you really can’t build a loving relationship on a foundation of guilt. The house will crumble. You’re not going to want to build a house on anything but love. Love must be the sure foundation and that means you’ve got to be willing to give yourself some regular check-ups. Ask the hard questions: Am I doing this out of guilt? If that’s the case then step back. Am I doing this out of fear? Again, maybe step back. Try to do things out of a heart of love as much as you possibly can. 

Pray often.

I’ve got people who are tough to love in my life and I honestly have to say so many breath prayers just to be around some of them. I pray things like: God, just be with me for this hour. God, help me to say the kinder thing. God, hold me to a higher standard. These are all not the most-fun prayers to pray but they actually work. Loving someone who is unkind to you or has a tendency to ghost you a little too often isn’t the easy road, let me tell you. A lot of people would likely tell you to just walk away. But I know my God. I know he equips me to handle the tough stuff. I know he covers me in the moments where I definitely don’t act as becoming as I should. I can tell you this: I won’t fight to love people well without God. I cannot even try on my own strength. 

As hard as it is, I would invite you to the pray for the person who upsets you. Yes, you are right, these will never be easy prayers to utter or inscribe. I honestly type up my hard-to-say prayers and print them out so that I can read them out loud in the morning and the evening. Is there always heart behind them? Sadly not. But I am honest when I say to God, “Hey, I really don’t feel like praying for this person but I am going to do it anyway. I am going to stop being a brat and just consider that this person might need more the prayers more than I need the comfort.” 

Watch your words.

I think it’s really important to become accountable to the words coming out of our own mouth when we talk about that hard-to-love person. Are we whining all the time? Are we complaining? Are we fumbling towards forgiveness or are we brewing ourselves a stiff mug of bitterness? Boundaries are key because people are constantly not hitting the expectations we set in our minds for them. We are constantly disappointed as a result. Brene Brown writes, “When we fail to set boundaries and hold people accountable, we feel used and mistreated. This is why we sometimes attack who they are, which is far more hurtful than addressing a behavior or a choice.” Be mindful of where you vent and you vent to. Be mindful of the words coming out of your mouth: are they hope-filled or filled with venom? 

Honesty hour.

Sometimes you just have to have an honest conversation (or a few dozen). Air out the room. I am not saying this is always an available option but, if you’ve got an open door to talk about it, I would say you should really try to be honest with the difficult person. Sometimes, it’s a matter of trying to understand what is making them so tough to love. What’s going on there? Is there something deeper rooted that makes them angry, harsh, mean or retaliative? Sometimes the best thing we can tell ourselves is, “I don’t know everything about this person. I don’t know what they might be holding back.” 

In this uncomfortable situation, lead with love. Confront with kind words like, “Hey, I really care about you” or “Hey, I really have to be honest that my feelings are getting hurt.” 

Encourage, even when they don’t receive positive feedback.

You will never go wrong with kindness. You just won’t. It’s how you take the high road. You pick kindness over and over again when it would be easier to match their meanness or just stop being there for them. The world of social media actually makes it easier to encourage one another in a way that’s harder to do in person. I’m not telling you to flee to a life lived only on a screen but little things like “liking” a photo or commenting on a story actually go a long way to other people. They feel affirmed. They feel seen. Even if they don’t say anything, your kindness is rewarded just by picking the better route. 

You’re tough to love too.

Really, we all are pretty tough to love. I am an expert at pointing out Lane’s flaws. He could say the same about me. The thing about love is that it was likely never designed to not be tough. Love is an endurance challenge. It’s an everpresent battle. It’s a fight that requires strength, stamina, and courage. Some years will beat you up, other years will give you more life than you can possibly imagine. I think there is something completely beautiful about living in 2018 and becoming the kind of people who don’t give up on someone when they get tough to love. 

Healthy boundaries.

Make no mistake, I am not proposing you hurl yourself at toxic people. I’m not telling you to show up at their house all the time and put yourself in the line of fire in the name of love. Boundaries are essential. Loving someone might mean you spend time praying for them. Loving someone might mean you spend time away from them, knowing you are not going to make them or yourself any bit better by being with them at this time. Loving someone might mean you stop initiating the text conversations and wait for them to come to you. It’s essential to protect yourself from people who hurt you. It’s like my friend Nate told me last year, “If you smell smoke in the kitchen, then get out of the kitchen. Otherwise, you’ll start smelling like smoke.” I think he was referencing something really true about us as people: we become more like the people we spend the most time with. If that person takes a real toll on your wellbeing, and you’ve got the space to distance yourself, then I would recommend doing so. 

Also, I recommend writing down the boundaries. Tweak them as you go. Look long and hard at them. Share them with a safe person who can help you tweak, adjust, and stay accountable. 

What are you learning?

I am a big believer that there is purpose in everything. We don’t just naturally see the purpose in everything. We have to work pretty hard to see it. We have to adjust our vision. I am a pretty reflective person and, when I encounter tough people and tough situations, I am always sure to walk away and reflect on what just happened: What did I learn? How did I handle that situation well? How could I have handled it better? What might God be trying to teach me? Do I need more patience? What’s one thing I can do to be kind tomorrow?

Self-reflection is crucial. God hardly ever uses the pretty and perfect moments to teach us something. It’s usually in the mud, in the trenches with people we’d rather not be left alone with on a stranded island. Take heart when you face challenges, M. Take heart because this was actually a really big victory. You emailed. You asked the hard question. You are seeking a better relationship and I think you are very brave. Write down your little victory somewhere and make the space to celebrate.


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Hi, I'm Hannah

I love writing about all things faith, mental health, discipline + and motherhood. Let's be penpals!


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