Tempted to Call Your Ex This Holiday Season? Read This First

Two things stand out about Lindsay Lohan's new Christmas movie, "Our Little Secret." First, Lohan's hair is flawless, almost compensating for the lack of chemistry with costar Ian Harding. Second, the plot unveils an often-overlooked dating strategy that unfairly gets a bad rap.

The holiday flick follows Avery (Lohan) unexpectedly encountering her ex, Logan (Harding), while celebrating the holidays a decade after their breakup. The kicker? They're at the house of the family of their new partners, whom they learn are siblings. Naturally, rather than laugh about the coincidence and carry on, they decide to keep it a secret at all costs.

Obvious spoiler alert: the film ends with them falling back in love. However, I'm here neither to criticize cinema nor to rant about the glorious nature of Lohan's comeback into the zeitgeist. She's like a Brat version of Marilyn Monroe, but I digress.

Although dating folklore preaches avoiding returning to exes, no two relationships — or breakups — are the same. So, while sayings like "an ex is an ex for a reason" have merit, so does the fact that many relationships don't work solely because they happened at the wrong place or the wrong time. As a professional proposal planner, I've witnessed it firsthand: some clients need the second time around to be confident enough to commit.

Experts Featured in This Article

Jason Robert is the founder of the matchmaking service The Hitchmen.

Alexa Andre is a sexologist and host of the podcast "In Bed With Alexa."

Time doesn't just make the heart grow wiser and fonder; circumstance plays a more significant role in dating than many of us care to admit. In "Our Little Secret," Avery had initially broken up with Logan to pursue a job opportunity. Naturally, choosing a paycheck over your heart doesn't sound sexy, but neither does giving up your career for a person who can still wake up one day and leave. There are all sorts of reasons why rekindling with an ex could lead to your fairy-tale romance — like if you broke up to attend different colleges and are now living in the same city as adults, or if you needed to experience the fish in the sea to realize you already caught the most compatible one.

In fact, I went on national television to discuss how turning 30 made me want to reach out to four men I dated in my 20s. My logic was that I had been fortunate to encounter many lovely guys, but I wasn't quite ready to seriously date them the way I would be today. If married folks can evolve away from each other and get a divorce, why isn't it possible to grow toward one another? (Of course, in the same interview, I also shared the story of when I got naked at the wrong apartment for an online hookup, so my risk tolerance might be higher than yours.)

Reopening your heart to failed former romances comes with inherent risks: an old wound can quickly reemerge, or you might face the reality that your ex isn't as eager to pick up where things left off. Still, if you ask Jason Robert, founder of the matchmaking service The Hitchmen, he suggests examining your past to better gauge your future. Part of his strategy with new clients is having them write down details from former relationships, including what they liked about that person and, more importantly, what they didn't. "I've had clients who broke up with their partner and then suddenly realize that they were actually amazing and had all the qualities they were looking for, but they weren't in the right mental state," Robert tells PS.

Robert utilizes his sports background to instill the importance of accountability in his clients. When reexamining past relationships, he instructs clients to question their role in why it didn't work out in the first place. "It's about really understanding who you are and what you are looking for in a relationship, and facing hard truths," he says. Time apart can serve as a vital opportunity for reflection and earnest dialogue.

However, sexologist Alexa Andre says that while things like sexual compatibility can be practiced and improved over time, you can't force a happy ending. Many factors come into play, such as who broke up with whom and questioning whether you're doing it because this person is suddenly all you can think about, rather than trying it like a trend or because you read this article. "Sometimes, we're really selfish," she says, "so try to think if they would be open to receiving whatever you're bringing to the table and if you're potentially playing with their feelings."

In other words, when reaching for stones left unturned, tread carefully, lead with your most honest intentions, and be willing to accept the different plausible outcomes.

When I decided to knock on the door of past flings, I was happy they were quick to open them, even if it was only to welcome me into their bedrooms. One man manifested as if god sculpted his body and personality exclusively for me: I couldn't figure out why we weren't together. There's a 10-year age gap between us, which nearly sent us into an existential crisis. Being 40 and 30 now seemed more sensible than when we were 30 and 20.

But life and romance weren't as simple as a moment — his masterful ability to dodge any commitment beyond a good time reminded me why I had moved on to more serious pursuits. I learned that a rock turned over was still a rock, and being older and wiser didn't give me the power to change anyone.

Jamie Valentino is a Colombian-born freelance journalist and romance columnist published in the Chicago Tribune, the Houston Chronicle, Men's Journal, Reader's Digest UK, Vice, and more. Jamie has worked as a travel correspondent, covering the 2022 World Cup from Argentina, siesta culture in Barcelona, and the underground nightlife scene in Milan.