Welcome to Bootleg Therapy: an advice column for wayward hearts. Think of me as your virtual stranger at the bar with a raspy voice and a weird scar on their cheek. The truth is in the worm at the bottom of the mezcal bottle. Submit your questions anonymously on brokebutmoisturized.com for a chance to be featured.
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Wannabe Fiancee
My boyfriend and I have been together for a few years and it’s by far the best relationship I’ve ever been in. We are both very happy and we express our shared happiness every day. However, lately, I’ve been hyper-focused on my desire to get engaged. I recently had to sign for a package that was delivered for him. Moments after the delivery arrived, he called me asking if he got a package and wanted to “make sure it was safe”. The package was an inconspicuous bubble wrapped bag with a small square box inside. I convinced myself it was an engagement ring. I searched the tracking number to figure out where the package came from. I stared at him intently when he came home and opened the package – it was some pomade for his luscious curls. (Why did that require a signature?!???!) My social media feeds are filled with other couples getting engaged, married, announcing pregnancies, etc. Lately I’ve been finding it hard to cherish all the little moments that used to bring me so much joy. Do you have any advice on how to keep the engagement blues at bay? Or just general advice on how to chill the fck out?
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Dear Wannabe Fiancee,
What. a. SCENE.
The tiny box! The required signature! Your eyes, possessed, gauging the degree of calm with which he undoes each little cardboard slot, and BOOM… hair product. A fire bursts in your gut, and you swear to never expect anything from anyone ever again.
For people like you and me, it’s these moments that come to define year two or three of every relationship. Countless times you’ll think someone’s about to drop to one knee and really, they’re just existing in a bubble of blessed oblivion, styling their gorgeous hair.
There’s a chance you wrote to me because I am happily engaged. I don’t exactly shout it from the hilltops that part of the reason we got here is because I applied the pressure. So unfortunately, I can’t honor your request to learn how to chill out because I didn’t chill out myself, nor do I necessarily think you have to. (For the record, I’ve actually never chilled out. Not once in my entire life.) But what I can do is help you discern whether your desire to be engaged is coming from a place of love or insecurity. And then maybe, we can make your case together.
The first thing I want you to do is name three good reasons why you want to get engaged right now. Notice I said “right now,” i.e., your reasons should convey a level of urgency proportional to how often you think about it.
Do you love your boyfriend so fucking much that to merely be his girlfriend cheapens the luxury of waking up beside him? Maybe you want children and your biological clock is more like a cuckoo clock and the noises won’t cease. Perhaps you come up with two reasons and call the last one a secret third thing. I don’t fucking know. All I know is seeing other people’s milestones on social media and feeling left out is a Bad Reason. Like, so bad that it almost negates any good reasons you have. It’s undoubtedly yanking you out of the present, which creates a false sense of urgency in relationships. So choose honestly.
Let me tell you why I wanted to get engaged to Andrew somewhat hastily (other than his being the cherry on top of everything). Three of the people I loved most in this world died around age 30. I now have an intense fear of abandonment. I also have an acute sense of mortality and want to do everything I can in this life ASAP. And of course, I was 30 years old and thinking about my waning fertility.
These reasons felt good to me, like they came from someone who is generally justified in rushing to the altar. But they were masking the ultimate root of my fixation—the one I smashed the deny button on every time I asked him “so, when do you think you’ll be ready?” The voice that told me, ever since I was a teen, that I would never know the feeling of truly being loved until I got engaged.
Yeaaah, well, that ring worked for like, a week before I tumbled from the cloud of short-term elation. And much to my dismay, those demons were not blinded by the light of my diamond. I was right back to questioning his behavior, whether his love would last. So I ask you: are there demons lurking in the shadows of your desire? It’s true, engagement is divine affirmation of love. But it is no medicine for chronic relationship anxiety and feelings of being unlovable. That, my dear, can only come from consistently flexing that trust muscle. Forget the myth that you need to be “healed” or whole to get married. But you should make sure insecurity isn’t the reason you want to.
It’s important you know that I advocate for an egalitarian partnership. One thing I hate about the traditional engagement model is that it betrays compromise. People love to act like having a say in when you get engaged drains some magic from the whole thing. How antiquated and delusional, to believe that love is truly patient and kind. Love is actually pretty self-centered and to get anywhere together, you must seek middle ground. So why should engagement be any different? It’s not forcing someone’s hand to say, “I am ready to take the next step with you.” If you both know you want to get engaged anyway, it’s healthy to share your ideal timelines, and meet halfway. Have you done that? Can you do that? If he meets you with vehement resistance, then we have a whole other problem entirely. Like, you may need to write back to me in that case. I’ll be on standby.
Your relationship will call for compromise after compromise. Use this as an opportunity to set a healthy precedent for big life decisions to come. You get a ring. Celebrations begin. Everyone’s happy.
Isn’t that what life’s all about?
Frozen at the Doorway
I'm a serial monogamist whose last 3 relationships have lasted 3-5 years each with perhaps a 2-month window of single life. My current boyfriend is a sweetheart. He has treated me better than anyone ever has, and I have not always been earning or deserving of that love in who I've been during that time (given I went through my Saturn return while we were together... which included some extremely traumatic, life-or-death-style stuff... cut me some slack). Anyway, despite him being an excellent, supportive partner who spoils the crap out of me, I'm craving adventure and want to live a dynamic life - which I don't feel like he wants. I worry that my independence is going to make him resentful. I sense he wants a house, to talk about kids, to get married - and those things feel like a distant future to me despite us both being very much at the peak age range (if not the latter end) of when these things tend to happen. My question is: how do you break up with someone when "nothing" is fundamentally wrong... except everything? Especially when you've been dating for a long, long time? How do you know when it's time? And what do you say?
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Dear Frozen,
You caught me. I’ll admit it. I don’t know what a “Saturn return” is.
But I do know that we tend to use a lot of unnecessary words to say “I’m bored.”
… what an elegant yawn you have.
You saw your life from a bird’s eye view and triggered that “holy shit, I’ve never been alone” moment and suddenly, everything you haven’t done came into focus. Moroccan medinas. Tea ceremonies in Kyoto. Stoic cowboys with wild, Wyoming hearts. I went through a similar situation in 2016. I can’t tell you how many times I scribbled, “if you want to fly, you’ve got to give up the shit that weighs you down” in my journal. Corny, but it helped. There’s no escaping the Eat, Pray, Love of it all.
You speak highly of how your boyfriend treats you. How someone treats us is only 50% of how they make us feel, the other 50% being who they are—stark naked, no walls. The characteristics and idiosyncrasies that compound to form their unique essence. It seems to me there is something fundamentally wrong here: you’ve either lost sight of that other 50%, or it was never there to begin with. Either way, it’s nothing to be ashamed of. And you needn’t address it when leaving him, because there’s no reason to make him feel worse than he already will.
Timing is sly in its neutrality, i.e., it will never be wrong and it will definitely never be right. It’s one of those things I decided was a non-factor a long time ago, because if we sit around waiting for it to be right, our entire lives will pass us by or whatever. Is that what you want for your hot years? (All years are hot years but let me be emphatic.) To pull the plug on a years-long partnership, you must surrender to time. Its ability to be both all-powerful and completely meaningless; the stretch of it you’ll leave behind and maybe call “wasted” when you leave him; the dreaded moment of actually doing the leaving. Let that shit wash over you like baptism. Because the longer you drag it out while feeling this way, the more you lie. And I may not know what a Saturn return is, but I do know karma and she stays strapped.
It’s always funny when people ask me how to say something. Friends have asked me to help caption their photos or respond to crushes for years and when I pitch my suggestion, they usually shoot me a weird, “thanks, but no thanks” kind of glare. This is because our own voice, no matter how shaky, will always be the one we really trust. And so the easy thing I can tell you is that this man deserves the truth, in your voice. That you’ve reached a personal impasse and if you don’t take this time to be alone and experience life without a partner, you will regret it forever. That it’s not fair to him to be with someone who’s not all in.
But the hard part (as if this whole thing isn’t one big hard part!) is preparing you for his protest. He may promise you the adventure and dynamic life you crave. He may be willing to table the whole kids and a house thing if it means keeping you. He may say he’ll do anything to stay together.
… and he may do it on the spot, or he may wait two weeks and break the radio silence with a heartfelt text. Catch you when you’re feeling his absence, maybe some regret. And it might sound believable, maybe even really appealing. Alas, he has changed! Is that something you’d want? For him to meet those needs? Or are you totally and completely committed to striking out on your own, being a single person in an increasingly lonely world?
If I scared you with that last line, it’s only because I’m practicing serious restraint in not divulging the full cautionary tale of my realizing the grass was only greener because I was looking at it through an Instagram filter. You seem committed to this breakup, and so breakup we shall do. Just prepare for an equal and opposite reckoning that perhaps the greatest adventure is building a life of love with someone who supports your independent needs, even if they don’t share in every crazy experience.
The jury’s still out on whether time is real. But one thing’s for sure: it is yours and yours alone. Now or never. So when you utter those hard words and free-fall into the unknown, just know that you are only better and truer for it.
Bootleg Therapy: An Advice Column #9
Love love the way you write and respond to these questions.
“How antiquated and delusional, to believe that love is truly patient and kind. Love is actually pretty self-centered and to get anywhere together, you must seek middle ground.”
BAR!!!!