Dating While Grieving: Unlearning What I Thought Love Was Supposed to Look Like
The year was 2021, and my world collapsed in the span of two months. My divorce was finalized, then two months later I lost my mom and my brother. When I returned home from the funeral, I was consumed with grief like a weight I couldn't shake. For months, I couldn't find the energy to get out of bed, let alone imagine a future where I might feel whole again.
But by the end of that year, something shifted. Maybe it was exhaustion from the heaviness, or maybe it was a desperate need to remember what it felt like to be alive. I decided I wanted to try dating, not because I was ready for love, but because I needed to get my mind off everything that was falling apart around me. I thought dating would be a step toward having fun and seeing life differently.
At 34, I was essentially starting over. My conservative upbringing had given me a very specific script for how marriages were supposed to work, but not dating. I was never taught how to date, only how to be a submissive wife. I had married young, in my early twenties, to the first person I'd ever been in a serious relationship with. Now, suddenly single and grieving, I assumed I was supposed to date like a wife-in-training. I thought I needed to be godly, agreeable, and celibate until marriage. I was looking for a man who would sit with me in my grief while I proved myself worthy of being chosen again.
I was putting in more effort than I even realized. I paid for myself and sometimes for both of us. I carried conversations, asked thoughtful questions, made sure things didn’t go quiet too fast. I juggled talking to multiple men because I thought that’s what you’re supposed to do. I cooked. I brought little gifts. I tried to be accommodating, soft, sexy, nonjudgmental, whatever I thought would make me more desirable. In hindsight, I was auditioning. Constantly. Trying to prove I was worth choosing. And it was exhausting.
When Everything I Thought I Knew Fell Apart
One of the first people I met seemed exactly like what I was looking for. He was kind, genuine, and thoughtful. On our first date, we sat in a restaurant and had the kind of deep conversation that made me feel seen. He felt safe, which was everything I thought I needed after the chaos of the previous months. We dated for a few months, taking things slow, really getting to know each other. This was exactly the way I'd been taught relationships should unfold.
When I decided to become intimate with the man who had been so kind and sweet to me, it wasn’t an easy decision. I wrestled with the thought of it because I was raised to believe that I should be celibate until marriage. But deep down, I didn’t believe that men would wait. I felt like I kind of had to — like it was expected — but even more than that, I was angry. I was still grieving. I had lost my mom. I had lost my brother. And the guilt that crept in was overshadowed by my rage with God. I didn’t want to think too hard about what was “right” or “holy” in that moment. I was tired of trying to follow the rules when the rules had never protected me from heartbreak or loss. I just wanted to feel something good. Something soft. Something that reminded me I was alive.
But when we finally became intimate, reality hit me like a slap. We were simply not sexually compatible. And I don't mean in some abstract, emotional way. I mean physically, our bodies did not work together. “It” was really small. I'll just say that as a plus size woman with curves, we were fundamentally mismatched in a way that left me feeling absolutely nothing during intimacy.
This isn't about judgment or shame; everyone deserves to find someone they're truly compatible with. But I also felt confused about why a man would pursue a relationship with me knowing our bodies were so obviously incompatible. More than that, I realized something that shattered everything I'd been taught about waiting: what happens when you do everything "right," when you wait until you're deeply invested, and then discover this fundamental mismatch?
I had already experienced terrible sex in my marriage. I was not willing to gamble on that again.
Turning Point
Ending that relationship, despite his kindness, forced me to reevaluate my entire approach to dating. That moment shifted something in me. I realized I was no longer interested in dating with celibacy or the idea of being a "godly woman" at the forefront. What I had really been craving, though I didn’t have the language for it yet, was a relationship where I could feel safe letting go of control. I was exhausted from always being the strong one, the planner, the leader. So I started dating from a different place, with the intention of understanding what it could look like to not always be in charge. That led me to explore relationships with traditional men. Not just out of curiosity, but because I wanted to experience a kind of balance I hadn’t known before, one where I could rest in my femininity and not carry everything on my own.
Part of the reason I sought out traditional masculinity was because of what I lacked in my marriage. I was married to someone who wasn’t a leader. I was the one managing the house, paying the bills, and making the decisions. And I kept wishing he would step up, that he would take charge in a way that made me feel safe and cared for. But every time I gave him the space to lead, he disappointed me. So when I started dating again, I was looking for the complete opposite. I wanted a “real man”, or at least what I thought that meant at the time. Someone who could fix things around the house, pay bills, take control of situations without me needing to spell it all out. I thought maybe a dominant man could give me that.
I tried dating apps hoping to find men who were my idea of traditional men. But what I found instead were men who were controlling, impatient, and entitled. They thought they could take up space in my life without earning it. They felt they had the right to tell me what to do before even getting to know me.
I would date men who would all of a sudden start calling me their girlfriend. Who would talk about marriage and wanting children. To other women that might be great, but I realized I didn't want that. They never asked my consent, just gave us a title that I didn't agree to. My needs weren't being met, and they really didn't care about my wants and desires. It didn't feel like love, it felt like possession. Dating seemed the same as looking for a new owner. And I hated the way that felt. But even that shift wasn't enough. Something deeper was still off.
The Exhaustion of Performing
Through all of this I realized I was putting in enormous emotional labor. I was being open and honest about what I was going through, sharing my grief and my hopes, trying to be the kind of woman I thought men wanted. But I wasn't getting much back. And I realized how much work was involved when I was cooking and cleaning, trying to be a good hostess; but I never got that same energy when I visited a man's house.
I learned to stop giving so much. I started quietly observing instead of constantly offering. I stopped leading with questions and let them carry conversations. They were not carried at all. Interactions became one-sided, with no questions or genuine curiosity about me. And I learned everything I needed to learn about a man without saying anything about myself. This next man I met proved exactly that.
Breakfast with a Stranger
One day I met this man on the app and it was early morning. Since our conversation seemed to be going well I asked him to meet me for breakfast. He warned me that his looks were a 5 and that his personality is a 10. He definitely used filters in his photos but I said why not just meet and see if we connect.
We go to a popular breakfast spot and he shows up in a wrinkled t shirt and swim shorts. He definitely didn't look like his pictures at all. While we sit there eating he's telling me he's in school to be a therapist, he runs his own business as a mobile bartender. He even showed me his banking statements so that I could see how much money was in his account. He told me his life story, abuse and neglect from his parents, and the struggles with self love. I was shown pictures of his house, filled with bottles of liquor. He laughed as he told me how he was recently drunk driving and woke up in a field with no recollection of how he got there. This man was 43. This was behavior that he should have outgrown by now. He was obviously an alcoholic yet in pursuit of becoming a therapist. None of this was funny to me.
I kid you not, this man did not ask one single question about me. I called him out on it and he said, “we change every minute of every day. Why get to know you in this minute when you will change in the next?” He then proceeded to keep talking about himself.
And then came the most surreal moment of all. He randomly told me how big his penis was. I definitely didn't ask. He then pulled out his phone and showed me a video of it. In the restaurant. In front of my plate of eggs and bacon. With children around. I was disgusted and embarrassed by the direction the conversation was going.
His followup calls and texts later that day were him saying that we were now together, he had bought me a few gifts, and couldn't wait to put all his focus on me. How that man could buy me gifts without any knowledge of what I liked will always baffle me. But I realized this was a full circle moment. Though he was physically different from the man in the beginning of the story, he did not provide the same level of safety, emotional availability and care.
I walked away from that breakfast not just baffled, but heartbroken in a quiet way. Because for all the chaos and absurdity, what stuck with me most was how little he cared to know me. It confirmed what I was starting to suspect: when I stopped giving and just observed, I wasn’t even a person to some of these men. I was a prop. They liked that I performed as a wife-in-training, but could care less about who I was at my core. And I was done performing for people who never even saw me.
The Ending of Performance
When I started this dating journey, I was a grieving woman trying to follow a script written by other people. Be godly, be submissive, prove your worth, wait for marriage, find an alpha male to lead you. I was performing femininity instead of living it, auditioning for love instead of expecting to be valued for who I already was.
I'm at a different place now, where I have deconstructed patriarchy and now I look back on these years and realize that was the problem. I believed that I was less than a man, and that I was a woman in need of a leader. My intuition was telling me that something was wrong and I couldn't figure out why. I'm now a liberated woman, but it took me years to get there. This was the beginning of realizing patriarchy doesn't serve me, and it really doesn't serve anyone else.
This is the beginning of a longer story about unlearning everything I thought I knew about love, sex, and what it means to be a woman looking for connection. Stay tuned for what happened when I stopped trying to date like a wife and started dating like myself. That changed everything.
Thank you for reading. If you’re enjoying these stories, I’d love for you to subscribe to my Substack. I share a new post every Sunday, and I can’t wait to take you further on this journey with me.
See you next Sunday,
Stacie