“That ship has sailed.”

There’s an age-old expression that goes, “That ship has sailed.” You’ve all heard it and you’ve all probably used it. But what does it actually mean? You’ve known the phrase since you were a child, but never really thought about it. Personally, I think it’s something that you only begin to understand as you get older.

In a literal sense, it means that the boat has taken off, and even if you wanted to catch it, you couldn’t. Because it’s already gone.

In a metaphorical sense, the phrase refers to missed opportunities. Or, it could also refer to something that you once had, but is now long gone. It has to be there in the first place to be able to sail away.

For example, your childhood. If you want to rekindle some aspects of your childhood, like your youthful exuberance, or your excess amount of energy, you couldn’t, because you’re not a child anymore. It’s over, and thus, that ship has sailed. It once was there, but not anymore.

Life is pretty long. Over the course of many, many years, a lot of things will change. Things will come and things will go. One day, you might feel one thing, another day, you’ll feel something else.

It’s almost sad when you wake up one day, and realize that something you used to care about deeply, suddenly doesn’t really matter to you anymore. It no longer stirs the emotions that it once did. In some respects, it could be a good thing. Maybe it was something you needed to get over. On the other hand, it could also be disappointing to know that you care about one less thing in this world.

I personally like the phrase because it’s very appropriate to many facets in life.

When the ship has sailed away, it’s long gone. It’s thousands of miles away floating somewhere in the sea, and it’s impossible to get to.

Whereas when you just know that feeling you once had is long gone, you also know it’s never coming back. No matter how hard you try. Maybe it was somebody’s fault, and maybe it was your own, or maybe it was just a matter of time.

I’m almost surprised that this phrase has never serves as the climactic quote of a dramatic romantic film. Picture the scene:

A really nice guy is in love with an absolutely beautiful girl. She’s a nice person herself, but she’s had an easy road in life because of her beauty, and every other man in the world thinks she is equally as beautiful.

The really nice guy asks the beautiful girl out dozens of times over the course of several years, but gets rejected every time. However, he stays optimistic, and is certain in his own naive way that the two will end up together.

Meanwhile, the beautiful girl dates asshole after asshole, choosing looks over personality, and continually gets used and mistreated. Finally, after being broken up with by another asshole, the really nice guy makes one more final attempt to ask her out. Not only does she reject him, but she becomes irate with him. She takes out all of her anger of all those assholes onto the really nice guy, and she embarrasses him and humiliates him, telling her to leave her alone, once and for all.

The really nice guy is devastated. His world is shaken, and for the first time in his life, he doesn’t believe that the beautiful girl is the one for him. What began as the final rejection, turns into the first day he begins to get over her.

Flash forward six months later. Finally putting the beautiful girl behind him, the really nice guy meets a girl. She’s decent looking, definitely not beautiful, but most importantly, she treats him well. He’s fairly happy, but deep down, he knows that something is still missing in this relationship.

One day, the really nice guy and his average-looking girlfriend run into the beautiful girl and her latest asshole boyfriend at a party. The beautiful girl sees the really nice guy with his girlfriend, and becomes kind of jealous, although she has no idea why. She flirts with him, but to her surprise, he reacts indifferently and wants none of it.

In the coming weeks, the beautiful girl thinks back to all the good times she had with the really nice guy while they were friends. She remembers the good memories, all the laughs, and all of the times he was there for her when she needed some one. With those thoughts, she comes to the sudden realization that she truly loves the really nice guy. She’s always loved him, but she never realized. So she approaches him and she says so.

“I love you,” says the beautiful girl. “I always have. I’m sorry I’ve treated you so poorly.” She kisses him. It’s a quick kiss, and the really nice guy lets her do it for a moment, but then pulls away.

“Listen, beautiful girl,” he says. “I’m sorry. I used to love you. More than anything. But I don’t anymore. That ship has sailed.” And then he walks away.

A montage with upsetting music plays and shows the beautiful girl in a state of sadness, crying while looking out the window. On the same night, the really nice guy is with his average looking girlfriend. She’s talking to him, but he’s not listening to a word. Instead, he’s staring off into the distance, thinking about the beautiful girl.

Two weeks later, the beautiful girl comes up with a plan that shows that she would go through extraordinary lengths to win back the really nice guy. She gets her friends in on it, maybe even some of the really nice guy’s friends, and implements the plan. It doesn’t matter what the plan is, but the point is, it shows how genuine her love truly is for him.

It all culminates in one final scene, in the rain, where the beautiful girl is standing face-to-face with the really nice guy.

“Why are you doing this?” says the really nice guy. “After all these years, why now? I’m with my average-looking girlfriend now. I’m happy! I don’t need you!”

“Are you happy?” She says. “If you say you’re happy, I’ll leave you alone forever. But just be honest with me. Are you happy?”

The really nice guy thinks long and hard, and several seconds pass. Finally, he lets out a whisper. “No. I’m not happy.”

The beautiful girl smiles and cries.

“I’ve never been happy,” the really nice guy continues. “Not unless I’m with you.”

The beautiful girl smiles even wider, and the two embrace in an ultimate, climactic kiss, with happy music blasting, and the camera spinning around them. They stop, and the beautiful girl speaks again.

“I thought you said ‘the ship has sailed?'”

“No, it’s hasn’t,” the really nice guy responds. “It never even left the dock.”


Wow. That was a lot longer than I meant it to be.

But next time you use that phrase, I want you to think about the context in which you use it.

Sure, the ship may have sailed, but remember, they have anchors for a reason.


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