In the movie Groundhog Day, weatherman Phil Connors is forced to relive the same day over and over again, in the same town, with the same people, until he suffers a complete mental breakdown resulting in numerous successful suicide attempts.

His salvation begins when he comes clean with his producer, and romantic obsession, Rita. For the first time in his life, Phil Connors manages to achieve through honesty what he couldn’t achieve through cynical manipulation, and he devotes his time thereafter to philanthropy and self-improvement.

Then it happens. After pulling off the perfect day, culminating in a longed-for night with Rita, Phil wakes up on February 3rd. “Today is tomorrow. It happened.”

That’s Groundhog Day’s happy ending.

Except it’s not the end for Phil Connors — it’s the beginning of a whole new nightmare consisting of these crushing disappointments.

Heartbreak

Most of the items on this list are based on inference and guesswork, but we actually get to watch Phil Connors making his first big mistake in the closing moments of the film.

As Phil and Rita venture out into the snow, Phil says, “Let’s live here”.

Uh-oh.

To understand the gravity of this remark we need to put ourselves in Rita’s shoes. As far as she’s concerned, Phil Connors is a self-centred, demanding colleague who managed to behave himself for exactly one day. He may have spent decades* harvesting information about her likes, dislikes, and personal history without her knowledge, but as far as she’s concerned he’s practically a stranger.

So imagine her horror as Phil invites her to move in with him, many miles from her workplace, friends, and support network.

The relationship that Phil Connors spent half a lifetime preparing for is probably over before the credits finish.

Anticlimax

Even if Rita were to take Phil up on his offer, there’s no way Phil should move to Punxsutawney. In fact, he should never set foot there again.

Why? Because he’ll never manage to live up to the impossibly high standard he set on February 2nd, when he saved the life of a mayor, played virtuoso piano in front of a crowd of partygoers, and won the hearts of an entire town through a series of slickly executed acts of kindness and heroism.

As they wake up to a new day on February 3rd, the citizens of Punxsutawney have every right to expect Phil Connors to be the person he was the night before: a generous and charming visitor with a supernatural gift for anticipating crises and fulfilling private aspirations.

But that’s not who they’re going to get. On the day after Groundhog Day, Phil Connors will be useless. Children will fall out of trees, civic leaders will choke to death, tyres will remain flat, brides will pull out of weddings, and chaos will reign in Punxsutawney.

Unemployment

It’s true that Phil Connors should stay away from Punxsutawney, but he won’t find much solace in his resident city of Pittsburgh.

Not only will this teeming urban environment be overwhelming for a man accustomed to the predictable charms of rural life, but it’s likely that Phil Connors won’t be able to earn a living as a weatherman when he returns.

The job of a TV meteorologist is made up of two components: being on TV, and predicting the weather. To give him his due, Phil Connors has maintained his live performing skills, honing his delivery to the extent that, on the morning of his final Groundhog Day, he causes rival broadcasters to shelve their own reports and take in his monologue instead.

But there’s absolutely no chance that Phil Connors still remembers how to interpret meteorological data after a career break lasting up to 40 years.

Insolvency

For the duration of his Groundhog Day adventure Phil Connors has never had to worry about how much he spends.

He splashes out on coffees and pastries for his colleagues, buys Wrestlemania tickets for two youngsters he hardly knows, and signs up for a comprehensive life insurance package from his old acquaintance Ned Ryerson. He also pays an inflated fee for expedited piano lessons.

These are relatively small expenditures, but they all add up, and they embody a troubling attitude to money. With no job and no sense of financial prudence, Phil Connors is on the fast train to ruin.

Estrangement

Imagine not seeing your friends or family for decades. Unless Phil Connors was a hermit back in Pittsburgh, that’s exactly what he has experienced — total estrangement from everybody he knows other than Larry, Rita, and, weirdly, Ned Ryerson.

He hasn’t seen the sister that Ned hit on for nearly half a century.

During that time, Phil Connors has changed beyond all recognition, becoming empathetic, principled, and sincere instead of cynical and mean. He has also lost the knack of being with his closest friends, as anybody would after a long absence.

Phil Connors’s transformation is positive, but his new values and demeanour are bound to unsettle the people who know him best, and who, as far as they’re concerned, only saw him yesterday.

No relationship can survive the complete transformation of one party overnight. Phil Connors is doomed to a lonely existence, or at least a long ordeal of building a new network and putting down fresh roots.

Remorse

In several of the Groundhog Days that Phil Connors lives through, he takes it upon himself to rescue an ailing homeless man whom he finds keeled over in an alley. He tries keeping the man warm, feeding him soup, and arranging medical treatment for him. None of it works. In every instance, the old man dies.

So Phil Connors gives up. On his final day, and presumably countless days leading up to it, he chooses to spend his time showing off at the big Groundhog Day party and sealing the deal with Rita. Helping the old man to pass on in a warm place with a full belly no longer serves his needs.

This approach clearly pays off for Phil Connors. The universe rewards his decision to let nature take its course. But, having helped so many, isn’t it reasonable to suppose that Phil Connors will be seized by remorse — like Oskar Schindler at the factory gates — at not having done all he could to ensure that the old man’s final hours were as comfortable as possible?

Answer: very reasonable indeed.

Death

Before Phil Connors arrived in Punxsutawney, he was a man of advancing years. But his years stopped advancing on February 2nd, and he spent many decades not having to consider his own mortality.

Not only was he unconcerned with the passing of time, but he knew for a stone cold fact that death simply wasn’t possible for him. No matter how many times he tried to kill himself, no matter how elaborate the method, he always woke up in one piece, listening to Sonny & Cher.

The only real contact that Phil Connors has with death during his ordeal is the tragically unavoidable passing of the old man. This is a grounding event, but it’s still happening to somebody else. Phil Connors is immortal.

Until, that is, he finds himself back on the merciless conveyor belt of time.

Bill Murray was 43 when Groundhog Day came out in February 1993, which means he was probably 42 during filming. Assuming Phil Connors is the same age, that puts him right on the cusp of a mid-life crisis just as he’s facing unemployment, poverty, probable weight gain, romantic catastrophe, social alienation, and madness.

God help him.

*Estimates vary, but director Harold Ramis put the duration of Phil Connors’s stay in Punxsutawney at 30–40 years, so let’s go with that.