Conversation with Jack Brennan

Belt talks to Jack Brennan, author of Football Sissy: A Crossdressing Memoir

You write with clarity in the book of an inner self-knowledge and shamelessness that goes back to childhood, even as it had to press against societal norms. "I’ve never suffered acute guilt or shame about sometimes wanting to feel like a girl... I’ve never felt 'wrong to the core.'" Unfortunately, we do see many moments where shaming comes from external sources. What does pride look like for you?

Pride looks like pushing yourself to show the world the side of you where your intellect rules, where you know with calm assurance that shame is undeserved and imposed bullshit. External sources are going to get you down sometimes; they are culturally so formidable. But you accept that as part of your non-perfect life – you don’t let yourself get blind-sided – and you resolve that you have plenty of power, derived from what’s right, to battle your way through those instances with your head high.   

In your preface, you use the words "embarrassing revelation" to describe the possibility that your colleagues might find out about your crossdressing. Has your interpretation changed?

The process of losing fear of “revelations” has been decades-long and glacially gradual. Yes, my interpretation has changed. I wound up creating the revelations myself with the Athletic article. The many years of reducing fear had given me enough confidence to believe that my colleagues’ reactions would be positive, and of course the amazing level of their support has changed my interpretation further. Give it up, people, to sportswriters and others in the sports media biz. They’re quite a wonderful group. The sportswriters in particular are my people.

But I think I remain right that coming out while still on the job could have been messy in many respects and ultimately embarrassing in some. I don’t harbor many regrets over waiting until retirement. I just was not up to the challenge before that. 

Let's talk about the book's title. One of my favorite lines in your text is this: "I have always called myself a sissy, perhaps as a way of taking on society’s scorn and finding that I can stand it." Will you expand on that?

For a white boy growing up in 1950s Texas, “sissy” was the most devastating epithet one could face. Boys were derided and sometimes utterly dismissed for any show of speech or behavior that was deemed to be “like a girl.” I didn’t face that horror myself, as my outward self has always been adequately and comfortably masculine. But my secret of course was wanting to sometimes dress and act like the girliest girl in the room. So, by definition of my culture, I absolutely was a sissy. 

And by calling myself one privately, I accepted reality and took away some of culture’s power to hurt and humiliate. I often have used it sardonically or sarcastically, just in daily life. My favorite restaurant was unexpectedly closed? “Tough luck for Sis,” I might say with a rueful chuckle. I’ve referred to myself as “Sissy, Sis or Sissy Girl” countless thousands of times, for all manner of reasons. Makes me a little tougher, ironically.  

This memoir is interwoven with pithy reflections in what feels like a cross-dressed voice. Will you tell me about those?

I can’t take credit for the “CD Life” inserts – a very helpful editor suggested those a ways back – but I liked the idea right away. They allow me to wax enthusiastically about “the process” at some length without getting in the way of the main narrative. They are a fun break from it, I think.

Why write a cross-dressing memoir now?

Of course I want to do my small part in joining those who have helped spike the overall shame factor by coming out. Queers do that when we’re able, and I totally hope my book can help some folks feel better about themselves. 

Altruism is not the whole story, however. I don’t know what other memoir writers feel about whether their brave and painfully told stories will achieve a “higher good” than just a successful book, but I bet I’ve got plenty of company when I say I recognize writing as one of my talents, and that I’ve been strongly motivated to use that talent to write a damn good book. A book that only I could write, and a book that’s compelling and praiseworthy for its execution as well as its message. Not so much to my credit, but I can lap up praise like a puppy, all day long and all day tomorrow.   

This book is almost as much about your beautiful, many-decades-long marriage and its growth alongside you as it is about your experience of queerness. What role has your relationship with Valerie played in your relationship to yourself?

Valerie gives me the inestimable human affirmation of knowing that I’m loved unconditionally, and no doubt my cross-dressing has imposed some difficult and troublesome “conditions.” A couple of times in the book I note with wonder that not one time did she ever even hint that she might break up with me over it. Valerie makes me feel good about myself, and isn’t that what spouses ideally do? So yeah, my relationship with her has played an absolutely pivotal role in, as you phrase it here, my “relationship to myself.”

Only six percent of marriages reach 50 years, as ours has, and I know there are many people out there with regrets over never having found a true soul mate. I try not to take it for granted that I am one of the lucky ones in this.