Rain Phoenix's It Happened To Me: My First Boyfriend Slept With My Second Boyfriend — And I Walked In On Them. I was 16.
It’s strange to even write about it, but it was my first experience of heartbreak in early life. One that would soon be eclipsed by the devastating death of my brother when I was 20.
Hello artists!
I can’t tell you exactly how long I’ve known Rain or how we first met. We have, together, been part of about 16 overlapping and undulating friend circles over the majority of our lives. I lived right upstairs from her for a couple of years in there too, maybe ten years ago, in a funny apartment set-up where some of our walls and some of our floors and ceilings were shared.
The day I launched AJPT (all those many months ago), I made a note to myself (not mental - handwritten on my wrist actually, so I wouldn't forget to do it before it washed off). The note said “Rain contribute.” I wanted that on that fledgling day because I have always loved Rain and her strength and intuition in particular. Her perspectives on so many aspects of life are always unpredictable, yet always consistent. You can count on Rain. Well, lo and behold (because we are deeply connected clearly), Rain texted me that same day saying she wanted to be part of this/you/AJPT.
Last time Rain was in New York, we met up at the apartment she was staying in down in Soho, and after being reminded to take off my shoes (why do I always just start clomping right in and ignore that policy, even when it’s so obvious that shoes are lined up at the door or elevator, and that no one else is wearing any?), we drank lots of cups of tea, maybe three each. We went for it and both had the caffeinated with agave version —this was a special occasion.
We talked and talked and talked, and as we did, she gave me some love advice that was so so different from what anyone else had suggested I do. That’s when Rain and I decided she would become AJPT’s relationship advice columnist, answering your questions and solving your quandaries about all types of relationship issues in her NEW as-yet-untitled column (we are kicking around a few title ideas, like “Q and Rain” and “Rain Theory” but would love to hear your ideas too if you want to share them). And don’t worry that I am all of a sudden becoming secretive about my own life - no way - I will resubmit that question Rain helped me with here, too, so you can see it and her genius answer.
Before launching this sure-to-be-unexpected advice column, I want to give you a little background on what qualifies Rain to be our relationship expert (you know I have never cared about degrees in stuff — just what a person has been through that makes them experienced enough to help other people using what they’ve learned). So Rain sent in this riveting “It Happened To Me” that I love her for so much.
I hope you love this story too, and I hope that her openness and vulnerability in telling it will help you feel instantly comfortable being that exact same way with her and with the relationship questions and topics you are now thinking of and going to send in (to Rain via jane@anotherjaneprattthing.com) or add in the comments here. They can involve anything to do with your friends or lovers (a word I never use out loud myself, but it doesn’t bother me when other people do) or partners (in business or in life) or the always entertaining crushes or flings.
I love you too.
-Jane
PS: Whenever you have a sec, check out this hot new invitation in Jane's phone and tell me if you're in on that plan with me. Xo
By Rain Phoenix
I promise this very clickbaity title is also a true story. I had to trick myself into writing it so it seems fair to trick you into reading it, too. I hope that by sharing this very personal story, it serves as a device to examine heartbreak, loss, and the possibility of transformation. Heartbreak can take many forms. This particular story can be qualified in the context of romantic heartbreak, but since the subject is vast, and has for better or worse touched my life in many ways, you may notice my propensity to find solace in its universality.
I was a teenager in the ‘90s and if you’re a Gen X-er, you know that comparatively the ‘90s were a very different time for teenagers in the sense that we lived in ‘the land before social media and cell phones.’ Heartbreak didn’t hurt any less, but at least we didn’t risk EVERYONE knowing about it. We could suffer it privately or, in my case, process it with my secret-keeping Scorpio best friend (let’s call her “Natasha.”)
If I’m honest, it happened so long ago that it’s kinda strange to even write about it. It no longer carries the same weight, though it sticks out as a pivotal moment—my first experience of heartbreak in early life. One that would soon be eclipsed by the devastating death of my brother when I was 20.
Losing him, for obvious reasons, was a very different kind of heartbreak. I still don’t completely comprehend it and I don’t know that I ever really will. That was a stratospheric loss that broke my heart into a million little pieces. It also secured heartbreak as a lifelong friend.
It led me to contemplate more deeply, adopting a kind of Socratic method when painful experiences arose, asking myself things like, “Did you think you would never experience pain?” "If so, why did you think that?” “Do you think you’re the only one who's in pain?” “Is heartbreak ‘baked in’ to personhood?” “When you see others suffering, does it repel you or make you more compassionate?” This method of asking and answering my own questions has served as a guide toward a deeper understanding of my life’s challenges, the possibility of transcendence, and the heartfelt wish to, when asked, share my findings with others.
Even at 16, I knew boyfriend number one (let’s call him “Jason”) and boyfriend number two (let’s call him “Kevin”) were queer. That didn’t stop me from having full blown crushes on them and so, when they returned the crush I was so happy! They both were just “bi” enough to be the safest boyfriends my inexperienced self could have hoped for.
All the romance, none of the danger.

I met my first boyfriend Jason at ballet class and there were immediate sparks between us. Thinking back on the time we spent together, I can smell the scent of amber resin he wore (to this day the scent I wear), hear the songs of Kate Bush (still one of my all-time favorite artists), and can almost see the Nagel-like women he drew in his notebook while we smoked clove cigarettes and made out. Back then, sexual ambiguity was a kind of armor, and labeling oneself seemed to limit exploration. I mean, we were teenagers. It was too early to “know” your preferences or too dangerous to admit them. Maybe this is true even today? (You’ll have to let me know in the comments.)
In regard to sexuality, I think back on my teenage years respectfully as my ‘research and development’ phase. I absolutely knew I preferred boys over girls but men kind of scared me. I’d had a few fun experiences with girls but sexually ambiguous boys were of more interest. Like most hetero leaning teenage girls, I thought about boys a lot. But hetero boys were unpredictable… or maybe too predictable. I guess I was looking for a somewhat controllable slow build into womanhood. Jason was dreamy, talented, interesting—but, eventually, just making out wasn't enough for me, so he and I parted ways. We remained friends.
Enter Kevin. He was more bi than Jason and that was the perfect balance, since I wasn't quite ready for full-on sex with straight boys. Kevin was a little older and it was fun to play at adulting with someone who could control their hormones. He had long curly black hair, big beautiful lips, an Adonis body, and an ‘up for anything’ disposition. I can still smell the coconut body lotion he used. (He taught me to always moisturize knees and elbows as they are more likely to get dry.)
He was adventurous and sensual. We drank too much coffee, wrote in our journals, watched movies, climbed old oak trees, listened to music, held onto each other tight, and even fooled around. He was crazy about me, and I him.
One evening, I went to pick up my best friend Natasha from the airport which was an hour plus away. She was coming to visit me, something she did pretty often since I moved from the West Coast (where she lived) to the East Coast. She and I loved going to the gay bar near the university (which was lenient on underage entry) to dance the night away. It became a kind of tradition when she came to town. I wanted to introduce her to Kevin and see if he wanted to come along.
Remember, this is the time before cell phones, and while he did know I was picking her up, he wasn’t expecting me. I can assume, now, he probably thought I planned to get some alone time with her on her first night in town. But I was desperate for them to meet and so made the executive decision to stop by Kevin's and invite him to join us.
I should note we were on the clock since I had a curfew. (Without cell phones how else could my parents know I was ok except to hear me come home at midnight?) I told her to wait in the car while I ran in to see if Kevin was still awake and up for dancing.
To paint the picture for what happened next, I'll need you to go ahead and cue your favorite Cocteau Twins record (in your minds…). I entered the apartment and turned my gaze up to the loft space which appeared to be transformed into a “Spandau Ballet” music video — curtains blowing, Cocteau Twins on the record player, candles twinkling —I immediately had a sinking feeling in my stomach.
I called up to him and there was the unmistakable sound of scrambling movements, the record scratching to a halt, and then, to my shocked eyes, Kevin’s face emerged from the gauzy curtains, soon followed by another recognizable face …wait …was that Jason?!
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