Is Meeting Your Ex a Good Idea? Handling Past Relationships and Nostalgia

Last week, while sipping my morning coffee, I received a message that took me back 30 years: my college sweetheart had found me on social media. Suddenly, memories of moonlit walks and late-night laughter flooded in. I’ll admit, my heart skipped a beat.

For many of us in midlife, the idea of reconnecting with an ex can stir up emotions and memories we thought were long behind us: it’s something worth thinking about carefully. If we do, how do we handle past relationships, manage nostalgia, and make empowered choices without getting lost in old feelings?

Why We Feel Nostalgic About Past Relationships

Nostalgia has a unique way of painting the past in warm hues. For many women over 50, reconnecting with an ex feels like peeking into a window where we were younger, freer, and full of possibilities.

I sometimes catch myself longing for that fearless version of me, the one who believed life stretched endlessly ahead. Meeting an ex can awaken those feelings, making us crave not only the relationship but the younger selves we were at that time.

But let’s be honest: nostalgia can blur why things ended in the first place. Before saying yes to coffee with an old flame, ask yourself: Am I truly seeking closure, a genuine friendship, or am I hoping to relive something that belongs in the past?

Look at the recent movie the Netflix Film Mother of the Bride, starring Benjamin Bratt and Brooke Shields. It beautifully captures that moment of surprise and emotional turbulence when a mother faces a former flame during a wedding celebration. Watching it, I couldn’t help but think of how even decades later, old relationships still hold power.

In my opinion, a real-life example that resonates just as much is Nancy Meyers’s Modern Love essay in The New York Times. At age 69, she reconnected with her ex-husband after 20 years, not to rekindle romance, but to rediscover a supportive, platonic friendship.

It’s a wonderful reminder that meeting an ex doesn’t always have to be about reopening old wounds or restarting old flames. Sometimes, it’s about healing, closure, and even a new kind of companionship that reflects who we are today.

How Can I Tell If I’m Ready to See My Ex?

In my experience and from talking to friends, reunions can either be healing or they can reopen old wounds. If you’re still carrying unresolved pain, it might not be the right time.

But if you’ve genuinely moved on, meeting an ex could feel like catching up with an old classmate—comfortable and drama-free. Be honest with yourself about where you stand emotionally before saying yes.

One of the great gifts of midlife is knowing your worth. If you decide to meet, be upfront about your intentions. I always recommend setting emotional boundaries, whether you want closure, curiosity satisfied, or simply to reminisce without reigniting romance. Boundaries keep your heart safe and your present life intact.

Revisit the Past or Keep Moving Forward?

Meeting your ex isn’t always right or wrong, it’s deeply personal. If you feel grounded and curious, it could be positive and healing and sometimes it can show you just how far you’ve traveled, emotionally, personally, and spiritually.

Even if the relationship ended badly, it shaped who you are today. I find it empowering to look back and think, “Wow, I survived that, and I’ve built a beautiful life since then”. That perspective is priceless.

But if you sense old feelings would outweigh any closure, it might be best to keep that chapter closed and cherish the memories from a safe distance. Sometimes, in my opinion, the bravest thing we can do is decide not to look back at all and instead keep pouring our energy into the vibrant, full life we’ve created for ourselves today.

Have you ever reconnected with an ex? What did you discover about yourself in the process?

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