Maybe You Shouldn’t Ask This Person Questions: How to Approach Toxic Relationships

I spend a lot of time talking about connection and impermanence.


Even the title of the “Questions You’ll Wish You Asked” journals implies the urgency with which I think we should consider our own fragility and that of our loved ones.


And yet, even while I ask you to zoom forward to the future and consider what you’ll wish you did in the present, I also don’t think you should trade your own peace in order to have a relationship with someone toxic, family or not.


I believe in working through issues and recognizing our life minutes as precious; in forging connections and also in having fierce boundaries: boundaries around your time, your heart, and anyone whose presence leaves feeling deflated, discounted, or small.


Yes, we’ll all be dead someday, so we should connect with each other now.

Yes, we’ll all be dead someday, so protect your energy now.

Both can be true.


Only you can decide who to let into the garden of your life: which relationships to nourish, which are worth toiling the soil of true intimacy, and which to keep just outside the garden gate.


My own imperfect family, which had branches that didn’t speak for years…

I believe that, as Arthur Shopenheur said, humans trying to love each other are like porcupines huddling together for warmth, inevitably inflicting accidental harm while we struggle to draw near. But I also believe that there are some porcupines who are particularly worth it, and some that are just prodding, painful, and harmful.

Even as someone with dead parents who’s constantly urging others to consider impermanence, my mission has never been “mend and connect above all else.” My mission is to help you live a true and meaningful life, one where you appreciate the sacred fleetingness of it all and savor the imperfect moments.


Some people have to do that from a distance with their families, and that’s okay.


So, dear reader, if you’re uncertain about approaching a toxic family member or navigating another tricky relationship, remember that there is no “should”; only you get to decide who is worth the porcupine prodding of love. And if you need a little help navigating this, I’ve included some questions to ask (yourself) about this person below.


Reminding you to tend to your own soil today. It’s precious. It matters.


~Melissa


Some questions to ask yourself when uncertain about a relationship in life:


How do I feel when I think about this person, or leave their presence?

How does this person make my nervous system feel when I’m with them?

What does this person’s presence in my life bring me?

Is there a boundary that can allow me to better care for myself within this relationship?

How do I think my future self would want me to treat this relationship?

PS: Do you know who the longest and most meaningful relationship you’ll ever have is with? YOURSELF. Consider spending time knowing, trusting, and loving that self a little more today. Here’s the journal I made for you to do so.

If it feels safe and good, consider writing down answers for your kids or asking questions of your family members in the Questions You’ll Wish You Asked journals. Find them here.

Do you know a motherless pregnant mom? I made a pregnancy journal just for her. It’s got all the thoughtful parts of a pregnancy log, but with the motherless mother in mind. Learn more here.