When Old Boyfriends Come Back Knocking — The Modern Advice Column Tackles The Ghosts Of Relationships Past Trying to Rekindle

Editor’s Note: Welcome to the second edition of Wit & Wisdom, the advice column that knows life’s questions rarely come with easy answers — but they could all use a sprinkle of sass and a dash of reality. Think of this as your regular dose of real talk, a nudge in the right direction or just the honest advice you’d get from that one auntie who’s seen it all.

If you’ve lived a good story, you’ve likely got a mental vault full of memories — some sweet, some bitter, some that’ll always stay on the shelf. But every so often, it’s fun to open it up, dust off a few old moments and reminisce. Who hasn’t heard that song (you know the one) and found themselves transported to the back seat of their high school sweetheart’s Toyota Corolla past curfew? Who hasn’t heard that name (oh, you know who) they haven’t said out loud in years and felt a flicker of something they can’t quite place? It’s normal and it’s harmless. It reminds us that we lived and we loved.

But what happens when someone drags those memories into the present? When they’ve lived entire lives, and now they want to flirt with what might’ve been — with you? Suddenly, the past isn’t just a memory. It’s an invitation.

That’s what this month’s letter writer wants to know.

Dear Wit & Wisdom,

Why is it that men only seem to appreciate me years too late? I’ve had more than a few old flames, former crushes and even men who never made a move back then resurface out of nowhere. They flirt with me, tell me how amazing I am — sometimes they even take it too far and make things overtly sexual. But these revelations always come long after they broke up with me, chose other people or built entire lives and families with someone else.

While a small part of me feels flattered, mostly I just feel annoyed — and, honestly, a little devalued. It’s like I’m only seen as “dream girl material” after they’ve built their lives elsewhere. It makes me feel like an afterthought, as if I’m suddenly an appealing option now that their lives are settled.

Why do men only seem to realize my worth when it’s too late? And how do I handle these belated flirtations without feeling like second place — or losing my patience or self-respect?

— Not Your Nostalgia Fix

Dear Nostalgia,

Move over, Ghosts of Christmas Past and Present. If only Dickens were around today to regale us with tales of the Ghosts of Paramours Past and Present — haunting our inboxes, reappearing in our DMs and delivering unsolicited confessions instead of festive moral lessons.

It’s an age-old conundrum, as Joni Mitchell famously put it: You don’t know what you’ve got ’til it’s gone. Or, in this case, what you could’ve had. What you think you could’ve had. Or the fantasy you’ve built in your head of what you could’ve had. Truly, a tale as old as time.

But why does this keep happening? Why didn’t they choose you when they had the chance?

Here’s the thing: it’s not really about you. Not in the way it should be, anyway. This was never about you not being enough. These bumbling boys didn’t secretly anticipate that they’d come crawling back years later as moored men with a well-timed, “Hey stranger, it’s been awhile.” This was always about them — their state of mind, their priorities, perhaps even their immaturity. Maybe these men weren’t the kind who could recognize your worth in those days. Not because you weren’t worthy, but because they weren’t ready to see the woman you are.

But also, hear me out: maybe they weren’t the only ones making the decisions back then. Maybe you were drawn to the unavailable — perhaps you were emotionally unavailable yourself. Or maybe, deep down, the longing was all you wanted at the time.

Not to get all psychologist-y on you (disclaimer: I am not one), but think about it: Were you truly open to a deep, emotional connection? Or did you, on some level, associate longing with love? Was it more about the struggle to get the guy than the guy himself?

And really, does anyone really know what the hell they’re doing when the options feel endless and we think we’re invincible with unlimited time?

But let’s be real — whatever the past was, we’re talking about the present now.

Those Old Flame Emails

When these old flames and long-lost admirers wheedle their way into your inbox, it’s not because they suddenly had an epiphany about how incredible and amazing you are (even though you are). It’s about them — their nostalgia, their restlessness, their sudden urge to romanticize the past. They’re not reaching out because they’ve come to the conclusion that you were their perfect match all along. They’re reaching out because life has settled down, there are no more highs to chase and the excitement of youth has given way to the reality of routine.

Lamenting the path not taken is a hell of a lot easier than reckoning with their own choices.

Instead of looking forward, they’re looking back. They don’t want to build something new; they want to revisit something familiar, something that lets them imagine a version of their lives where they “Got it right.”

To them, in hindsight, you’re a missed opportunity. The missed opportunity. The road never traveled. The fruit never tasted.

It’s selfish, really. They made their beds, they rolled around in them, drank all the champagne in the mini fridge and now? They want to sleep in a new room and wake up to a new view.

But you’re not a box on their midlife regrets checklist, nor are you not some long-forgotten treasure they get to unearth at their convenience. You’re not some fantasy for them to indulge in. You were (and are) always worth choosing. And guess what? You’re no consolation prize for a man who has woken up to what he really needs and wants now.

Too little, too late, boys.

So how do you handle these late-stage revelations? It depends. If their attempts to rekindle the spark entertain you, enjoy the flattery and smugly bask in the knowledge that this is who you are to them now. If they annoy you, don’t respond. (We women are frustratingly taught to be accommodating, but you do not owe anyone anything, including a response to a man who is using you to stave off his own midlife crisis.)

And if Mr. Man crosses a personal boundary? Shut it down. “It’s too bad you realized these things too late. Take care and good luck!” should nip it in the bud right quick.

My girl, you were always worth dating. You were always the first choice. The people that recognize your value won’t need years, regret or hindsight to figure that out.

Until next time, be wise and wonderful,
W&W

You’re always worthy to me, and so is your nostalgia, your restlessness and your sudden urge to romanticize the past. Slide into my inbox at witwisdomadvice@gmail.com and check a box off your own midlife crisis list.