Sobriety exposed how I treated my past partners. I’m ready to date again, but do I even deserve to find love?

Dear Kai,

I’m a single white trans guy in my mid 20s looking to date for the first time in a couple of years. The reason I stopped dating is because I used to be a heavy drinker, and I did some really embarrassing, awful things to the people I dated (mostly cis queer women). Finally, one of my partners told me I was being abusive and broke up with me. I went into a sobriety program, stopped drinking and managed to work things out with all the people I hurt. I never got called out publicly, and I’m still a part of the queer community where I live (though I don’t have the greatest reputation, understandably). I know this has to do with my privilege as a white dude. I know I’ve been given more chances that I deserve, and I feel really ashamed of myself. I’m worried that if I start dating again, I’ll fuck it up and hurt somebody. What can I do? Do I even deserve to date again? Would it be better to just stay single forever?

Repentant White Trans Dude

Dear Repentant,

How do we forgive ourselves for crossing lines that seem unforgivable? How can we trust ourselves, knowing that we have betrayed our loved ones’ trust? These are age-old questions with no small amount of personal pain and struggle behind them, and I can hear them echoing as I read your letter.

If you’re familiar with my column, Repentant, then you will know by now that I don’t give straight-up answers to questions like yours. I do, however, start with the assumption that everyone—everyone, no matter who they are or what they have done—is worthy of love and capable of loving.

This foundational belief is, to me, the very basis of a politic rooted in love and transformative justice, which is the notion that harm cannot be effectively addressed through means of punishment and disposability. Love politic and transformative justice hold that we must transform the conditions that have led to harm, as well as the people who have perpetrated harm.

This doesn’t mean letting harm doers (including ourselves) “off the hook,” however. On the contrary, one of the most beautiful and radical acts of love is holding someone in both compassion and accountability at the same time.


Here, I will make a bold suggestion, Repentant, if I may: I believe that one of the most important aspects of your work as an individual who has hurt people in the past is to learn how to responsibly love and forgive yourself. In doing so, you will improve your own life, and you will also create greater capacity for safety and healing in your relationships and your community.

Queer communities already know so much about abuse, shame, trauma and isolation. We know so little about healing, forgiveness, or coming back into safe-enough relationships through a journey of redemption.

Here is where your privilege as a white man—which I think you accurately name as part of the reason you haven’t been exiled or ostracized by your community—might be used for good, Repentant. The “white man’s burden” is a colonial idea that has traditionally encouraged white men to see themselves as conquering saviours. The inverse of that is simply working on yourself to be a better person. Because of your privilege, you’ve been granted an experience of mercy that not everyone in our community receives. Instead of staying in self-imposed isolation, you can be brave and show the people around you what having humility, working on yourself and taking responsibility look like.

The idea of self-compassion and self-forgiveness as a pathway to greater integrity and better relationships is not unique to me, or to transformative justice—indeed, it is an ancient notion that can be found in many communities and contexts. The meditation teacher and psychologist Tara Brach asserts that: “Feeling compassion for ourselves in no way releases us from responsibility for our actions. Rather, it releases us from the self-hatred that prevents us from responding to our life with clarity and balance.”

I love this statement because it speaks powerfully to our responsibility to work towards self-compassion. There is such a thing as healthy guilt and shame, and these emotions exist for a reason; they help us learn and protect us from humanity’s worst instincts. But feelings of guilt and shame that fester become trauma and self-hatred, and self-hatred does not, in fact, protect anyone. Nor does it turn us into better people.

On the contrary, I suspect that self-hatred prevents us from reaching our full potential for kindness and goodness to others because self-hatred is an emotion that keeps us looking inward. Being good to others, on the other hand, requires our full capacity for being present and connecting with the world outside of ourselves.

All this to say, Repentant: you are allowed to heal, to work toward self-forgiveness and to date again. We become loving and lovable people through practising love, on ourselves and with others. If we all wait to date until we are perfect, we will all be waiting forever—and we can’t improve without practise.

This is all well and good, but perhaps it doesn’t address your fear that you might harm others as you start to reopen your dating life. Abuse and harm are slippery things—caught in the spiral of our own crises, we often do not recognize when we are being harmful, or how to stop, until it is too late. This is why being told when we are acting abusively can be one of the greatest gifts we ever receive from the people in our lives. When we are aware of our actions, we become capable of changing them.

In practical terms, Repentant, I would suggest making full use of whatever healing, self-help and support resources are available to you—perhaps the sobriety program you mentioned has follow-up groups or counselling available. As you probably know, most cities and towns have chapters of Alcoholics Anonymous and other mutual aid groups for folks recovering from heavy drinking. Addiction recovery coaching and counselling can also be powerful supports, if you have access to them.

As you make contact with these resources, I suggest asking explicitly for help with growing healthy relationships; there are so many people in this world who have struggled with causing harm and making amends as the result of heavy substance use. Many of them are devoted to supporting others moving through that same journey. You do not have to do this alone.

Indeed, Transformative Justice teaches us that the process of redemption—becoming trustworthy in the sense of being worthy of trust—is not necessarily something that happens in imposed isolation, as the prison-industrial complex suggests. Rather, one of the most powerful ways of making amends is to live and be in community as someone who is capable of owning their mistakes. By honestly and authentically living in your truth and building safe new relationships, you are showing your former partners and your community (as well as yourself!) that they no longer need to fear you.

Abusive patterns thrive in isolation, Repentant. When we hide ourselves in shame and shut ourselves away from the world, we run the risk of losing perspective and falling back on hurtful coping mechanisms. Our best selves shine when we can see ourselves reflected—for better and for worse—in the loving gaze of others.

You can also set up harm reduction practices to ensure that your dating partners have greater access to safety. One common strategy I have seen a lot of folks use is simply being upfront about their relationship history: You can tell your prospective partners that you have committed harm in the past and let them decide for themselves whether or not they feel comfortable moving deeper into intimacy with you.

Note, however, that this strategy should be applied with care and nuance—you don’t necessarily need to overwhelm people with an intense story about your past right away. Beware as well of turning such disclosures into covert requests for emotional labour from new partners, as this can make for some truly terrible first dates!

If you are trying to gauge how to balance appropriate honesty with good boundaries, I would suggest that it’s often enough to casually mention very early on (before or during the first date) that you used to be a heavy drinker, that you’re in recovery now and you are working on being a better date/partner. It’s relatively easy to work this into first-date conversations because you have to pick a place to meet up, and you can say something like “I’d love to hang out/go out/have fun with you somewhere, though I should mention I can’t do alcohol because I used to be a heavy drinker and ______.” Keep it simple and short, at least at first. The other person’s response will let you know whether they need/want to know more.

Another harm reduction strategy is to set up an accountability pod beforehand. I’m constantly talking about “pods” in this column, and I don’t intend to stop any time soon because they are a fantastic strategy for creating safer communities. Originated by the Bay Area Transformative Justice Collective, an accountability pod is essentially a small group—say, two to five people—you trust who have consented to support you in a particular area of your life.

You might, for example, ask a pod to do regular check-ins with you to help you keep track of how you are acting in new relationships. You could also ask a pod to take on the responsibility of holding you accountable if you were to do anything harmful (this is a big ask, so consider it carefully). With their consent, you can give your pod folks’ contact info, and an explanation of their role, to new partners when the time is right—I’d suggest as relationships start to heat up or enter more serious territory, which is when most abusive patterns start to emerge.

Finally, Repentant, I would invite you to go slowly, following the pace of your own comfort, pleasure and recovery. Intimacy is a wonderful thing, but it can also be powerful and triggering, and I would advise anticipating strong feelings coming up in response to new intimate experiences. The more aware you are of your own needs and boundaries, the less likely you are to make mistakes or harmful decisions. Haste is often the enemy of wisdom, so let yourself move with care.

Finding our own goodness—becoming the people we want to be—takes hands-on practise, which can be frightening. It can also be thrilling. Be as gentle and kind with yourself as you want to be with your partners because this will help you to be a better partner! Developing healthy intimacy is like panning for gold: It takes time, patience, a sharp eye and a deft hand. It also takes faith that you will find it; the goodness in you, the goodness in others. The gold in the shame and the silt of our souls. Keep looking, Repentant. Let yourself shine.

Need advice in a hurry? In our new video series “Ask Kai: Quick Tips for the Apocalypse,” Xtra columnist and author Kai Cheng Thom offers concrete suggestions to help keep your relationship happy and healthy in these harrowing times. Watch the episode below.

Kai Cheng Thom is no longer a registered or practicing mental health professional. The opinions expressed in this column are not intended or implied to be a substitute for professional medical advice, diagnosis or treatment. All content in this column, including, but not limited to, all text, graphics, videos and images, is for general information purposes only. This column, its author, Xtra (including its parent and affiliated companies, as well as their directors, officers, employees, successors and assigns) and any guest authors are not responsible for the accuracy of the information contained in this column or the outcome of following any information provided directly or indirectly from it.

Kai Cheng Thom is a writer, performer, and social worker who divides her heart between Montreal and Toronto, unceded Indigenous territories. She is the author of the Lambda Award-nominated novel Fierce Femmes and Notorious Liars: A Dangerous Trans Girl's Confabulous Memoir (Metonymy Press), as well as the poetry collection a place called No Homeland (Arsenal Pulp Press). Her latest book, Falling Back in Love with Being Human, a collection of letters and poetry, is out now from Penguin Random House Canada.

Keep Reading

In the midst of despair, how do you find the will to go on?

“We have a calling, here in this decaying world, and that is to live and to serve life with every precious breath that is gifted to us”

I’ve met someone amazing, but I can’t stand the way he smells. How do I talk to him about it? 

Kai weighs in on how to have a “scentsitive” conversation with a new date 

Queer and trans families are intentional. They take the shape of what you and your loved ones need most

In the nine-part series Queering Family, Xtra guest editor Stéphanie Verge introduces us to people who are redefining what it means to build and sustain a family

Valentine’s Day gifts for every queer in your life

Shower every love in your life with gifts galore this Valentine's Day