It's late at night, and your mind starts to wander. Back to times that seemed better. Back to memories of an old flame. A person you used to speak to every day is now just a trace of an outline in your memory.

Maybe you put on "Heat Waves" by Glass Animals to really set the mood as you reflect.

Sadly, this person is no longer in your life because of a mistake you made. You gave up on them too soon, and now, as you check their social media to see how they're doing, you realize just how big of a blunder you made.

They have the job they were working toward when you were together. Their profile photo is of them standing on a beach with their happy, healthy family. That could have been you, but you lost patience. You gave up.

This happens in the NHL all the time. A general manager or team drafts a player, only to get frustrated by their development—or lack thereof. So they move on, dealing the skater away to another organization that sees some promise.

A year or two later, they're contributing at the level they were supposed to, and the original team is left wondering how they whiffed on their own internal player assessment.

Valentine's Day seems like the perfect time to look back and examine times when NHL teams or general managers pulled the plug on their relationship with a player just a bit too soon. Perhaps, unsurprisingly, some of the league's bottom-dwellers show up on this list more than once, signaling why they can't climb out of the basement.

Which one of these do you think stings the most as their O.G. club looks on as their former player succeeds elsewhere? Who has your favorite team given up on that you regret the most? Sound off in the comments and let us know.

Now on to the heartbreak.

And a shoutout to Lyle Richardson and Lyle Fitzsimmons for contributing some of these ideas to this column.

Anthony Duclair

He's not the biggest name on this list, but Anthony Duclair is the genesis of this story idea. And it's amazing what the right fit can do for a player's career. Five NHL teams gave up on the former third-round draft pick before he clicked in a top-six role for the Florida Panthers.

To be fair, skating alongside two of the most creative players in the sport has helped boost Duclair's production. Yet you can't ignore the fact that he's 100 percent jelled with Jonathan Huberdeau and Aleksander Barkov.

He's not the one driving that bus, but man has he made the most of the opportunity to be a passenger. The right wing bounced between five franchises within the first six seasons of his career and was a target for criticism during several of those stops.

His time with the Arizona Coyotes and Columbus Blue Jackets was particularly tumultuous. Duclair requested to be traded out of the desert after becoming frustrated with his role, and while in Columbus, then-head coach John Tortorella had unpleasant things to say about the forward.

Florida took a chance on him in 2020, and Duclair has rewarded the team with steady production since. His first season with the Panthers earned him a three-year extension, and this seems like the perfect fit for the once-wayward scorer.

Filip Forsberg

It's important to consider the context when examining the Washington Capitals' decision to trade Filip Forsberg for Martin Erat back in 2013 at the trade deadline. The team was struggling to do much damage in the playoffs during that portion of the Alex Ovechkin era and badly wanted to add some win-now talent.

Then-general manager George McPhee was frank when discussing the trade.

"You're here to win. We've been in that mode for a while. This is six years of trying to win a Cup," McPhee said, according to Katie Carrera of the Washington Post. "We had our rebuild phase, we sort of rebuilt things on the fly here, but we'd like to continue to make the playoffs while we're doing it."

Erat appeared in nine regular-season games for the Capitals and scored just one goal. Washington then lost in the first round to the New York Rangers via a soul-crushing 5-0 Game 7 loss. Erat appeared in four of those contests, scoring no points and accumulating four PIMs.