“Mystery in the History”: Should You Revisit a Past Love?
The other night, I was out catching up with a friend over hookah and a drink. We were people-watching—something I love to do, especially when I’m not in matchmaker mode—and we noticed an older couple sitting nearby. They weren’t being loud or flashy, just… present with each other. Holding hands. Sharing quiet laughter. The kind of scene that makes you pause.
Courtesy of Netflix
My friend leaned in and said, “Do you think they’re married?” I said, “Either that, or they’re having an affair.” We both laughed.
Eventually, curiosity got the best of us, and we struck up a conversation. Turns out—they were married, but only for just two years. But here’s the twist: they were high school sweethearts who had reconnected at their 20-year reunion. Life had taken them in separate directions: college, jobs, marriages. But the connection had never really faded. And when they found each other again, the timing finally made sense.
It immediately reminded me of something Aleeza Ben Shalom, the matchmaker from Jewish Matchmaking on Netflix, says often: “Is there a mystery in your history?” She encourages clients to look at past relationships—especially ones that didn’t end in flames, but maybe just faded due to timing—and ask, “Is there still a ‘there’ there?”
I’ve started incorporating that very question into my own client interviews at Single to Shaadi. When reviewing past relationships, I don’t just want to know what went wrong—I want to know what almost went right. Because sometimes, that missed connection wasn’t a failure. It was a preview. And maybe, just maybe, it’s time for a sequel.
Timing Is Everything—And That Includes Desi Dating
In Desi culture, we’re taught to move on quickly from relationships that didn’t result in shaadi because we’re always fighting against that invisible clock and “log kya kahenge” mentality. Many South Asians who come to me later in life—either post-divorce, or after years of chasing the “perfect partner”—realize they once had a connection that was deep, meaningful, and aligned... but life pulled them in different directions. Oftentimes, this past relationship is holding them back from moving forward with someone new—not just because of lingering feelings, but because they're comparing every new prospect to an idealized version of their ex. They might even find themselves mentally measuring new matches against the warmth, familiarity, or emotional safety they once felt. This kind of emotional comparison—often subconscious—can make truly opening up to someone new almost impossible.
This is especially common for those who dated in college, during internships, or right before a big move. At the time, we’re prioritizing ambition, visa status, or family expectations. That sweet, stable, kind person may not have fit your vision board, but they sure felt like home.
Now, with more life experience (and hopefully, emotional maturity), you might see those past loves through a new lens.
So, Should You Reach Out?
The question of whether to revisit an ex is complicated. And no, I’m not saying you should text your toxic ex who made you cry every other week.
But if there’s someone in your past who was kind, who brought out the best in you, and where the breakup wasn’t messy—just mistimed—it might be worth reaching out. Especially if you're "still friends" or follow each other on social media—that's a natural on-ramp to re-acquaint yourselves with each other’s current lives. These quiet check-ins, the occasional story view or birthday message, can act as soft openings to something more intentional. Social media, for all its faults, can be a gentle reminder that someone is still out there, still growing, and maybe even still open to love. As one Redditor in r/love put it: “Sometimes, it’s not that the love died. It just went dormant.”
Of course, proceed with wisdom. Here’s a framework I use with my clients:
Ask yourself: Was it the right person, wrong time? Or the wrong person altogether?
Would reconnecting open a door or just reopen a wound? Sometimes we romanticize the past simply because it’s familiar, not because it’s functional. Make sure your curiosity isn’t being driven by loneliness or nostalgia alone.
Are you both in a new life stage where a relationship would make sense? Have the circumstances that pulled you apart changed? Have you changed? If you're both in a healthier, more grounded place—and your goals are aligned this time—it could be the right time for the relationship to truly work.
Real Talk: Desi Parents Love a Good Rekindling
You know who loves a rekindled love story? Desi parents. Once they get over the shock of “Wait, him again?”, they usually love the idea of marrying someone they already know (and possibly liked back then). Bonus points if your ex has a stable job and no recent scandals. Maybe the families had met and there was an explicit endorsement from both to go ahead and move forward.
Riteish and Genelia Deshmukh
In Bollywood, rekindled romances have long been a beloved trope—think of Kajol and Shah Rukh Khan in Kabhi Alvida Naa Kehna or even more recently, the real-life union of Riteish and Genelia Deshmukh, who continue to be a beloved Bollywood couple after decades together. Their enduring bond—rooted in friendship, mutual respect, and shared values—is a reminder that sometimes the most powerful love stories aren’t the flashiest, but the most consistent. While they never actually split, their love story, which began on the set of their debut film, showcases how deep, long-term connections can continue to grow stronger over time. It’s a compelling example of how a youthful spark, when nurtured with time and maturity, can evolve into a lifelong flame. And across the ocean, we have Bennifer—Jennifer Lopez and Ben Affleck—who rekindled their early-2000s romance almost two decades later. It wasn’t just nostalgia; it was timing. Grown-up versions of themselves recognized the potential they had once left behind.
Final Thought: Could You Already Have Met Your Person?
We live in a culture obsessed with “the next.” The next swipe. The next event. The next match. But what if the person you’re meant to build a life with is someone you’ve already met? What if your love story isn’t a brand-new beginning—but a beautiful reunion?
So this week, I invite you to reflect: Is there someone in your past who deserves a second look? And if so, what’s stopping you from saying hello again?
