It was my mother’s idea to go on a double date. “Wouldn’t it be fun?” she asked, her eyes bright with excitement. I hesitated, picturing how strange it might feel to be sitting at a dinner table with my mother, her boyfriend, and my boyfriend all together, like some unorthodox Diwali dinner. But she was insistent, so I caved. We found a cozy restaurant with dim lighting and soft music, and the four of us settled into the evening. It was surprisingly enjoyable, filled with easy laughter, shared stories, and the kind of warmth that comes from a sense of being among people who understand you.
But later that night, when the evening was over, my boyfriend pulled me aside. “Your mom deserves better than that guy,” he said bluntly, concern etched across his face. I blinked, caught off guard, unsure of how to respond. Then, my mother called me later to report a similar conversation. Her boyfriend had told her, with an air of pity, that I deserved better. We laughed about it the next morning, but there was an unspoken understanding between us. We never went out with both of them together again. It was one thing to navigate the confusing world of love on our own; it was another to see the mirror reflected back at us so clearly.
I’m in my 20s, and my mother, in her 50s, is freshly separated, wading back into the dating world after decades of marriage. It’s odd to think of her on a date, wearing a dress she hasn’t touched in years, sitting across from a man she’s just met at a café. It’s even stranger that we’re both navigating this romantic landscape at the same time, in parallel worlds that somehow keep converging.
As strange as it is to say, my mother and I have become each other’s biggest critics and champions in our romantic lives. Just last month, she demanded my boyfriend come over for dinner to meet her properly. “If he's going to be a part of your life, I need to know what he’s like,” she insisted. Meanwhile, I was making similar demands of her. “You’re going on holiday with this guy? Not until he comes over and wins my approval,” I declared, crossing my arms in a way that I knew she recognized — it was the same way she used to stand when she was firm with me.
Our roles had reversed, but we were playing the same game. We’ve both been trying to act as gatekeepers for each other, as if by some strange twist of fate, the mother-daughter bond now came with a two-way approval process for love interests. It’s a ridiculous dance we do, but one that shows just how deeply we care about each other’s happiness.
Not long ago, she was the one offering advice while I dissected every tiny detail of my love life, from crushes to heartbreaks. She had a knowing way about her, a confidence that made it seem like she had love all figured out. Now, though, it’s as if she’s back in her teenage years, uncertain and excited, trying to decode the language of modern dating. I never thought I’d be coaching my mother on what a 'thirst trap' is or helping her craft the perfect reply.
Two years ago, she came to me, hesitant and anxious. (It was usually me on the back foot, trying to convince her to let me take the car out.) We were sitting at the dining table, the aroma of freshly brewed coffee filling the air between us. She took a deep breath, her fingers tracing the rim of her cup. "I think it's time I put myself out there," she said softly, her eyes searching mine for a reaction. For a moment, I was silent, processing the weight of her words. This was the woman who had been my pillar through every scrape, now revealing a vulnerability I hadn't seen before. A mix of emotions swelled within me — excitement, concern, and a subtle shift as I realized our roles were beginning to blur. "I'm glad you're ready," I finally replied, reaching out to squeeze her hand. "We're going to have a lot of fun."
Soon after, she met someone. As she talked about him, I felt a twinge of something I couldn’t quite place. Was it jealousy? Amusement? Or was it the unsettling realization that we were now living out strangely similar lives?
The more she told me about him, the more I couldn’t help but see myself reflected in her story. The way she overanalyzed every text, wondered if she was coming on too strong or not strong enough. I recognized the hope in her eyes, a hope that I had once carried for someone, and maybe still do. “Do you think he’s interested, or just being polite?” she asked me, her voice carrying the kind of nervousness that I thought was reserved for people my age. It was then I realized how love, no matter your age, is always a bit of a mess.
Sometimes it’s hilarious. Like when I catch her trying to decipher the meaning behind a heart emoji or agonizing over whether to use a smiley face or just a plain period at the end of her message. Other times, it’s surreal. There was this moment when we were both getting ready for separate dates, standing side by side in front of the mirror, scrutinizing our reflections. She turned to me, holding a pair of earrings up to her ears. “What do you think? Too much?” she asked. I laughed and shook my head. “Nope, they’re perfect,” I said, feeling a wave of pride mixed with a bit of something bittersweet. We were two women, in different stages of life, preparing for a night that held the promise of new beginnings.
But it’s not always fun and games. There are the late-night conversations where the laughter fades, and we talk about the hard stuff. Like when she tells me how strange it feels to be putting herself out there again, the anxiety of hoping she can still find someone to grow old with. “I thought it would be easier at this age,” she admits one night. I nod, understanding more than I care to admit. “It never really gets easier, does it?” I say, thinking back to my own relationships that fizzled out or exploded spectacularly. The awkwardness of first dates, the thrill of connection, the sting of rejection — it’s all still there, no matter how many years have passed.
Despite our efforts to protect one another, we can’t seem to escape our own patterns. We started sharing our dating experiences, comparing notes like we were cramming for an exam, swapping stories about our latest fights with our boyfriends. As she recounted hers and I told mine, it hit us both at the same time. “Wait a minute,” I said. “You just described me.” She looked at me, eyebrows raised, realizing it too. We had the exact same shortcomings in relationships — hyper-independent, volatile, always keeping them at arm’s length. It was like looking into a mirror.
The things my boyfriend complained about — how I would blow hot and cold, how wouldn’t open up — were the same things her boyfriend complained to her about. It was both amusing and unsettling. We thought we were so different, my mother and I, each unique in our approach. But here we were, realizing that our flaws ran deep, echoing through generations.
And then there’s our type in men. We both fall for the same kind, like moths to a flame. We complain to each other about the nice guys — the ones who are stable, kind, the ones who would treat us well. “He’s just so...good,” I’d say, frustration leaking into my voice. My mother would nod sympathetically, understanding something that others couldn’t. Despite knowing these men are the ones who would make us happy, we find ourselves drawn to the ones who are a bit rough around the edges. The ones who keep us guessing, who thrill us but inevitably leave us hurt. We know they’ll mess us up, yet we can’t help but be captivated. When my mother shares her stories of heartbreak, they sound painfully familiar. “He was sweet, but he was just...too available,” she confesses, rolling her eyes. I laugh because it’s the same excuse I’ve used, the same ridiculous logic that makes perfect sense in the heat of the moment.
At times, it’s like living in a sitcom. I hear myself saying things to her that she used to say to me. “He’s not good for you,” I scold, half-meaning it, half-knowing that she’ll ignore me just as I ignored her advice when I was younger. She nods, pretending to listen, and then goes right back to doing what she wants. I do the same. She gives me warnings, tells me to guard my heart, but then watches me fall headfirst into the same traps she did. It's a dance of hypocrisy and understanding, one that binds us together more tightly than ever.
It’s funny and sad and beautifully human, this journey we’re on. For all our efforts to break free from our flaws, to find the ‘right’ kind of love, we seem destined to walk these paths side by side, making the same mistakes and learning the same lessons. In the end, maybe that’s what love really is — a cycle we can’t escape, one that connects us through our shared vulnerabilities and missteps.
And so, we keep going. We sip our smoothies, laugh at our absurdities, and console each other when things don’t work out. We know we’re a mess, but we’re a mess together; navigating love’s minefield one step at a time.
Maybe, just maybe, the apple doesn’t fall far from the tree — not in who we are, but in how we love. And maybe that’s okay. She’s my first love, after all.