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Wellness > Sex + Relationships

I’m Going Through A Breakup During Cuffing Season, & I’m OK With That

At the start of fall, I was in a relationship with someone I thought was my person, my soulmate. She and I spent the tail end of summer excitedly talking about our plans for fall and winter — “cuffing season,” as people often call it. We talked about going on pumpkin patch dates, spending Halloween together and having matching costumes, celebrating Thanksgiving as a couple, and seeing Christmas lights together. But, seemingly out of nowhere, my seven-month relationship came crashing down. Never in a million years did I expect us to break up — or that I’d spend this cuffing season alone.

The truth is, I was looking forward to fall and winter more than usual — mainly, because it would be the first time in ages that I was “cuffed” during cuffing season. I felt lucky that I wouldn’t have to spend the season trying to find someone. But three days into October — the start of cuffing season — I found myself single and alone. 

It felt strange to know that all the plans we had made together weren’t happening anymore, and it hurt. Not only had I lost someone I’d spend cuffing season with, but I also lost the person I planned to spend the rest of my life with. Overnight, all of our conversations about getting an apartment together and having a small courthouse wedding didn’t matter anymore: it was all gone. I was heartbroken and couldn’t understand how my future — and a whole world I spent seven months building with this person — disappeared overnight. 

For days after, I did nothing but think and think and think. Going through a breakup is hard enough as is. But experiencing that heartbreak during cuffing season is even harder. Between my friends excitedly telling me about the new person they’re seeing, watching people around me fall in love, and all the cute couple reels I keep getting on Instagram (Instagram, I hate you), how could it not be? It all felt like a cruel reminder of what I lost and what could’ve been. 

Just because I went through a breakup and am spending cuffing season “alone” doesn’t mean I don’t have love in my life.

But after a few days and after a lot of reflection, I realized something: what we had didn’t collapse overnight.  Our relationship ended as a result of a series of little things that became too much for both of us — such as my own mental health struggles as a result of relationship OCD. 

I always thought that being in a relationship would make me happy and things in my life completely OK, but I learned the hard way that that isn’t the case. After we broke up, it hit me. Nothing and nobody can heal or fix me — at the end of the day, it’s up to one person and one person only: myself.

Once I realized that, I finally accepted that I needed help and decided that I wanted to heal. As time goes on, I’m starting to feel more and more OK. It hurt losing the person I thought I’d spend the rest of my life with, but honestly, I now realize it was for the best. People say that time heals, and honestly, I’m starting to believe it.

I never thought I’d be saying this, but so much good has come out of that relationship ending. Since the breakup, I’ve been slowly discovering who I am outside of a relationship and getting treatment for my OCD. The relationship and breakup helped me realize how bad it had gotten, and hitting rock bottom made me realize that this wasn’t something I could handle alone. 

And while I’m “uncuffed,” that doesn’t mean I’ve been experiencing this season alone. I started to push myself out of my comfort zone as a way to do exposure therapy for my OCD, and I’m so glad I did. Even though it was scary at first, I ended up making new friends and finding myself. I also found myself experiencing things I never thought I’d be able to, such as going out with new friends in entirely new places.

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photo by grace tran

A couple of weeks ago, I thought I’d be spending Halloween at my then-girlfriend’s side, dressed as an angel while she was my devil. Now, I’m spending it with my new friends in a small town that I’m starting to feel is mine.  A part of me mourns the fact that I’m not going to have the sweet, sapphic Halloween I had looked forward to for months. But another part of me is super excited to continue cuffing season — the Thanksgiving celebrations, the Christmas lights, and all of the excitement of the season — cuffed to myself. 

For the first time, I’m finally OK with being alone. I don’t have to find someone to spend this season with to make it special. I have someone to do all the things I want to do with: myself. Just because I went through a breakup and am spending cuffing season “alone” doesn’t mean I don’t have love in my life — I very much do. Even if the love around me isn’t romantic, it doesn’t mean it’s any less special.

If you or someone you know is seeking help for LGBTQ+ mental health or safety concerns, call The Trevor Project‘s 24/7 Lifeline at 866-4-U-TREVOR (866-488-7386). You can also reach out for instant message or text message support via TrevorChat and TrevorText, respectively. For additional resources for trans people, call the Trans Lifeline at 877-565-8860. In an emergency, contact the National Suicide Prevention Lifeline at 1-800-273-TALK (8255) or call 911.

Grace Tran is a recent University of Houston graduate, aspiring writer, and passionate storyteller. She believes storytelling has the power to foster connection, challenge stigma, and help people feel seen. Gracie is passionate about mental health advocacy and encourages open, honest conversations about emotional well-being, identity, and the experiences that shape who we are.

Grace aspires to be a queer Asian Carrie Bradshaw. She writes for the wellness vertical and explores relationships, sex, mental health, identity, and the beautifully messy reality of navigating your twenties. She enjoys blending personal reflection with cultural commentary, whether she's unpacking dating trends, discussing self-growth, or examining the nuances of queer life. Her goal is to write articles that resonate with readers while offering representation, comfort, and a fresh perspective.

Grace aspires to build a career as a magazine and digital media writer, creating thoughtful, engaging stories that inform, entertain, and inspire meaningful conversations. She hopes to amplify underrepresented voices, especially within queer and Asian communities, while continuing to write stories that leave readers feeling understood, empowered, and a little less alone.

When she’s not writing, Grace is trying to navigate life as a twenty-something, collecting new experiences, and finding beauty in life's beautifully messy moments.