Stuck in Layover Hell: Why I Needed This Space

Stuck in Layover Hell: Why I Needed This Space

If dating after 40 is like travel, then I’ve been living in layover hell. You know the kind: you’re exhausted, you’ve already missed your connection, and no one will give you a straight answer on when—or if—you’re actually getting to your destination. That’s where I’ve been in love: circling the gates, no real clarity, plenty of delays, and just enough false hope to keep me sitting at the terminal.

I was married for almost 25 years to a man who was, let’s just say… not the easiest travel companion. I won’t go deep into that chapter, because frankly it’s not the story I want to tell. What matters is that after two long-term relationships (one marriage, one partnership that didn’t end in disaster but didn’t go the distance either), I was left in a place where I had to rebuild my confidence, my identity, and my sense of worth.

And let me tell you, doing that while dipping your toes back into the dating pool? Whew. It’s like trying to pack a carry-on after years of overpacking—you suddenly realize you’ve forgotten the essentials, and everyone else seems to have a secret hack you don’t know.

The App Phase (a.k.a. My Terminal B Experience)

Like many women, I started with dating apps. Not because I believed Prince Charming was lurking on Bumble, but because… well, where else do you meet people these days? I had kids at home at the time, so I was careful—trying to keep my personal life separate from motherhood, sparing my boys the awkwardness of “Who’s Mom texting now?”

The apps, though, were a trip. I quickly realized that swiping was less about connection and more about endurance. Unavailable men came out of the woodwork. And the supposedly “single” ones? Half of them lived two states (or a continent) away and wanted to “just see where it goes.” I would hear, “Let’s not make it too complicated.”

Sure, Brad. I’ll hop on a flight for a man who can’t even spell my name correctly (or give me his).

Heading out on A Date, Contemplating Life

It was exhausting, disheartening, and honestly funny in a “cry-laugh on your couch with wine” kind of way.

The Truth I Didn’t Want to Admit

Here’s the thing: I thought I was just looking for companionship. A dinner date. A partner in crime. Someone educated, funny, nice-looking, maybe even adventurous like me. And yet, every time I got close, I felt myself pulling back.

Why? Because those long relationships—the ones I don’t want to live in anymore—left me with baggage. (See? Travel metaphors work everywhere.)

• I’m wary of commitment.

• I still have to remind myself daily that I am worthy of love.

• I’ve yet to feel like I get straight answers or honest connections from most men.

It’s not that I don’t believe love exists. I do. I just don’t know why it feels like it’s hiding at a gate in another terminal, and I don’t have the boarding pass to get there.

Stuck in Looping Pattern

I’ve worked hard to be independent, adventurous, and pretty damn fun. I’ve been told I’m reasonably pretty. I’m a giver, a pleaser, a woman who loves adventure. So tell me—why is it harder to find and genuinely connect with a good, kind, funny, educated man than it is to get bumped to first class on a fully booked flight?

The Laughable Truth

Here’s the part that actually makes me laugh (because if we don’t laugh, we’ll cry, right?):

It’s not that I’ve had no successes. There have been some bright spots. A few good dates. A connection here and there. Some wonderful stories I’ll share (names changed, of course). But after the initial start-up, there is an aborted take-off. The relationship goes nowhere, and worse yet, the man becomes a ghost.

But the overwhelming reality is this: dating at this age is full of contradictions. Men tell me they want a confident, adventurous woman, but then they get intimidated when I don’t orbit around them. They say they want honesty, yet I can’t get a straight answer about something as simple as, “Are you actually available?”

It’s maddening. And it’s funny. And it’s painful. And it’s real.

Why I’m Writing This

This is why I needed to create this space. Not to wallow. Not to bash men. But to tell the truth about what it’s like to try to find connection after 40 (or 50). To laugh about the absurdity. To share the failures and the successes (yes, there are a few). To remind myself—and maybe you—that we’re not alone in this.

In a Lounge, Somewhere in the World, Waiting for my Plane (or Train, actually)

Because if I feel like I’m stuck in layover hell, I know other women are sitting in the same terminal, staring at the departures board, wondering when their number will be called.

So here it is: the lounge. The gathering spot. The place where we get to share our stories, sip a metaphorical glass of wine, and remind each other that even if the flights keep getting delayed, we’re still in this together.

Your Boarding Pass

So here’s my invitation: Share your own “layover hell” story. Or share a success. Or just introduce yourself and tell me where in the world you’d rather be waiting for love to show up.

Because this journey isn’t just about whether we find “him.” It’s about whether we can find ourselves, laugh in the chaos, and maybe—just maybe—enjoy the layover along the way.