Ask Kai’s greatest hits

This week’s Ask Kai is Kai Cheng Thom’s 100th—and final—advice column. Kai isn’t going anywhere: she’ll still be contributing regularly to Xtra, as a columnist and feature writer, bringing her signature blend of wit, compassion and insight to a variety of topics. But after more than four years of giving advice, it felt like the right time for a change. 

I had the pleasure of editing Kai’s columns for many of those years. Here, I’ve collected some of the most noteworthy columns from over the years. 

How do I hire a sex worker?

This story, the most-read Ask Kai column of all time, helped establish Kai as a go-to source for information people had always wanted to know but were too afraid to ask. 

I’m a cis guy looking to date a trans woman. How do I start?

Dating and having sex with trans people—or as trans people—came up in columns a lot over the past four years. From how to start dating trans people as a cis person to questions from trans people about how to navigate complicated dynamics during sex, Kai’s column became a much-needed source of sex and relationship advice for trans folks and the people who love them. 

I’m an old, out and proud lesbian. Am I transphobic if I don’t want to have sex with trans women?

This column caused a stir online when it was first published—mostly among angry, anti-trans posters who appeared to have only read the headline and not explored further. But Kai’s take on this sensitive topic is smart, compassionate and timely. Among those who did take time to sit with the piece, it just may have been mind-changing. 

I have herpes. Do I have to tell every single partner about it? 

From debunking some sexual health misconceptions to exploring sexual ethics, this much-read column provided nuanced advice on a frequently Googled topic.

My friend has been lying about being poor for years. How can I ever trust them again?

Not all Ask Kai columns were related to gender or sexuality. Readers also frequently wrote in about friendship and community. Sometimes the questions—like this one—felt all too real.  

How much space should white-passing people take up in the antiracist movement? 

Ask Kai columns often acknowledged and explored the ways power manifests within queer and trans communities and how intersectionality plays into the ways we experience—and are treated by—each other and the rest of the world. 

My friend detransitioned and has started to become transphobic. What should I do?

Kai’s column often felt topical. This column, written as detransition discourse started to gain steam online, added an important trans perspective to a conversation in which the loudest voices are still largely cis and anti-trans. 

I see myself as different from cis women. Does that make me a “bad” trans woman? 

Some of my favourite Ask Kai columns were those that spoke directly to trans people, answering questions in ways that weren’t at all geared toward cis audiences. The above question from a trans woman navigating her identity comes to mind, as does one from a trans man who questioned whether not wanting to socially or medically transition just yet meant he was letting his community down.