The QLP Questionnaire: Kara Westerman
"I generally don’t feel queer enough. I’ve had relationships with men and women my whole life. And I married a trans man. But my family didn’t know about his identity until after he died."
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I live and work in East Hampton, New York, where I am collaborating on book with my late husband about his life as a trans man, our lives together, death, resurrection, transformation, and waking up. You can find serialized chapters on my Substack.
Kara runs a daily writing accountability group called Writers Daily Dive. They meet on Zoom from 1-2 p.m. EST. The group writes together in silence on Zoom after a brief chat Monday-Thursday. On Fridays, the group reads aloud and offers feedback. It’s open to everyone, with a suggested monthly subscription to support the space. You can find more information here.
What is your age, where in the world do you primarily live, where did you grow up?
I am 63. I grew up in California, have lived in New York, Los Angeles, Savannah, Georgia, Berlin, Germany, and I am hoping to move to Italy.
How do you define yourself on the LGBTQ+ spectrum?
Bisexual; married to a trans man; widowed.
What is your relationship status?
My husband died in 2020, and I’m still getting through that. No dates, just a book collaboration between me and my late love.
Do you have an “ideal” relationship status?
Nope.
What is the biggest misconception about being single or in a relationship?
That you have work at it, and the the harder you work the more successful it will be. Until my husband and I found each other, we didn’t know that happy relationships were actually quite easy.
When was your first intimate moment? Was it with someone you liked? Did you feel pressured into it?
I was in love with the Artful Dodger when I was seven, and it was downhill from there. I think first kisses were mostly scary in 1970s California. It was always interwoven with pot and alcohol and paranoia. Of course the horrible forced intimacy that stand out was when we move in with my mother’s boyfriend and later my stepfather. When his drunken father came to visit, he took me up to my room, bolted the door, and shoved his tongue down my mouth. An awful secret. Turns out he had being doing this and much worse to all the girls in the family, including his daughter.
How would you define love? Is it the thing you work at for a long period of time? Or is it the strong feeling you feel for someone right from the beginning for no reason?
There are so many kinds of love! That unbelievable feeling you get from mutual attraction is such a strong indicator, but mostly with me it has been disastrous. When my husband and I fell in love, it developed so slowly that we didn’t realize it.
We went from friendship into love, and then falling in love. All of those states, including a strong erotic connection, which started to wane when he was diagnosed with cancer.
Taking care of him in his last years was amazing as our love grew even more. I never knew that it could be boundless. When he decided to die, and go into hospice, we were married. And I got into his hospital bed with him and stayed for five days. That love that just kept growing has not even stopped with his death. We are collaborating on a book together!
Does the relationship fill your deepest needs for closeness with a person? Or do you prefer not to share every part of yourself?
My relationship did, but it never had with anyone in the past—probably because I went for attraction rather than shared interests.
When did you come out to family, friends and others for the first time?
I never did. I generally don’t feel queer enough. I’ve had relationships with men and women my whole life, so my family know. And I married a trans man. But they didn’t know about his identity until after he died.
Did you have any LGBTQ+ role models as a child or teenager? What do you remember about images of same-gender or queer relationships or messages you gleaned?
BOWIE!!!! John Cameron Mitchell’s creation, Hedwig. She is in my pantheon of gods. I often ask myself: What would Hedwig do?
Are there any pivotal pop culture moments that you credit for teaching about love and/or relationships?
BOWIE!!! HEDWIG AND THE ANGRY INCH!
Do you have a “found family” or “chosen family”?
I do, because I have been in AA for 24 years and, between old friends and AA friends and Substack friends, I have a lot!
What is your relationship with your biological family (if any)?
We are pretty close.
What do you (did you) like about dating as a LGBTQ person? What do/did you dislike?
I don’t lead with that identity and neither did my husband. I guess I have always had the luxury of just being me.
Have you had any difficulties dating or finding/keeping a relationship?
Not until now at 63. I guess I am more sober, more picky, and tired!
What’s the most surprising thing you have learned about relationships from your perspective?
That you keep having versions of the same dynamic until you are so bored that you change.
Let me share how I met my husband: We were friends, and then really dear friends. I asked him to be the subject of an oral history interview that I was conducting for a course where we would cut the interviews together into radio pieces. He was very private and asked that I not reveal his name at the time. I know he wouldn’t be bothered at all now, but at the time, he hadn’t ever told his whole life story to anyone in depth.
We sat for two two-hour sessions. When I replayed the taped interviews, I realized that we were totally in love with each other. I was like, “Ohhh, FUCK!” I could hear it in the interviews. Nick was married to a friend of mine at the time. I decided to stop interviewing him and stop seeing him, but eventually he got it out of me. We had fallen deeply in love without letting ourselves really know it. These interviews and transcripts are some of my most prized possessions, and they are all included in the book we are working on together.
Have you experienced heartbreak?
Always and forever. Dating men and women who were generally addicts and drunks was an experience of 40 years of heartbreak. Even when I got sober at 40, I still had years of crazy affairs before I met my husband in AA. And then the biggest heartbreak was and is his death in 2020 at 65. That changed me and my heart forever.
How would you term your sexual relationship with your primary partner? Has that changed over time?
Our sexual relationship was wonderful and passionate, and then it changed when he got sick. But our love kept growing!
Are there any things that standard heterosexual relationships have that you feel are out of reach or that you wish you had or could achieve?
No, I don’t think there is really any difference for me. But for people who want to have children the old-fashioned, biological way, I guess that might be important. It has never been something that I wanted.
Have you ever been in a polyamorous relationship or would you like to be in a situation that doesn’t involve just two people?
I’ve had threesomes, but they were silly and full of angst, and I don’t think it was anything but boring.
Are you married? Have you ever wanted to be? Whatever the response, explain why and what your hopes, dreams and journey has been like.
I married my husband in the hospital about five days before he died. We were worried about my ability to inherit his family home. Otherwise, I don’t think we cared about marriage.
Have you had a difficult time navigating the “roles” you should play in a relationship?
No. But I did hate cooking three nights a week when my husband insisted we divvy up that duty.
What is your philosophy about relationships?
There actually is a right person out there to make your life something worth living. You might have to go through a lot of trouble along the way, but don’t stay if it’s miserable. It’s jut not going to get better.
Any advice you’d give to someone younger than you who thinks it’s impossible to find love?
I would repeat what I said before: “There actually is a right person out there to make your life something worth living. You might have to go through a lot of trouble along the way, but don’t stay if it’s miserable. It’s jut not going to get better.
BONUS:
We all need more inspiration. Recommend something that influenced or helped shape you significantly that you’d recommend to someone else.
Books: Anything by Nabokov, Evelyn Waugh, Edward Albee, poetry by Hafiz.
Movies: Hedwig and the Angry Inch, All of Us Strangers, Jules et Jim, Dog Day Afternoon.









I am so happy to be in this good company. Thank you, @Jerry Portwood !
Love this. You've had a fascinating life, Kara. And thanks, Jerry, for bringing us her story.