On a cold winter's day in New York, an American man and a British woman reach for the same pair
of black gloves, in a department store. On seeing that it is the last remaining pair,
they both politely offer it to each other. While trying to decide who gets it, an elderly man
comes from behind and snatches the gloves for himself. Startled by this, the duo stops him
and asks that he returns the glove. He refuses at first, but they concoct a story on the spot,
which persuades him to return it. Feeling happy at their accomplishment,
the lady offers to treat him to brunch at her favorite restaurant, down the street, named
"Serendipity." On arriving there, the man gets a milkshake and is impressed by the taste, prompting
him to ask how she found the place. She explains that she was captivated by the restaurant's name,
which is one of her favorite words- "Serendipity," which means 'a fortunate accident'.
While conversing, they learn that they are both in relationships,
and try hard to mask their mutual disappointment on hearing the news. When they're done having
their meal, the duo leaves the restaurant and make their way downtown, where the American
introduces himself to her as Jonathan. He asks for her name and phone number in return,
but her only response is a peck on the cheek. After which, she enters a cab and speeds off.
Disappointed Jonathan walks around town before returning to the restaurant,
when he discovers that he left his winter scarf on the restaurant's table.
He goes back to look for it, only to run into the mystery woman from earlier,
who apparently also forgot something there. Seeing this as a second chance,
he asks that they spend the remainder of the night together. Luckily, she accepts the offer,
and the duo soon after heads over to a nearby ice rink to skate for some time,
while relishing in each other's company. Later that night, the woman agrees to give
him her number and writes it down on a piece of paper. However, as she's about to give it to him,
a truck drives past and blows the paper right off her hands. The British lady believes that,
that is a clear sign that they are not supposed to be together, but Jonathan
refuses and asks for another chance. After repeated pleas, she obliges and asks
him to write his number down on a dollar bill, which she uses to buy a mint at a nearby kiosk.
On returning to him, she explains that if they are meant to be together, fate would
ultimately lead the dollar bill back to her. Thus, giving her the chance of reaching him again.
Instantly, Jonathan voices out how unfair it is that he's the only one who wrote his number down,
and asks that she return the favor. After some thought, she agrees and spontaneously comes up
with a plan. She shows him a book and writes her number on it, explaining that she would sell it
at an undisclosed book store the next morning. Hence, also giving him a chance at finding her.
For the final fate test, she takes him to a hotel and makes them enter separate elevators,
opposite one another. She asks that he pick a random floor while she does the same, explaining
that if they both pick the same floor, it would mean that it's their destiny to be together.
Before the elevator doors close, the mystery lady finally reveals her name to him as Sara, while he
watches as the doors of her elevator get shut. Coincidentally, they both push the button for
the 23rd floor, but Jonathan's ascend is greatly delayed when multiple people get in the elevator
and make numerous stops at many floors. Getting to the 23rd floor,
Sara waits for him for a long while before ultimately giving up as she assumes he picked
a wrong floor. Sadly, Jonathan arrives just a few seconds later and narrowly misses her.
A few years after that night, Jonathan is at his engagement party with his best friend,
Dean, who gives an embarrassing speech as the attendees raise their glasses for a toast.
After the party ends, Jonathan kisses his fiancé goodnight and heads on home for the night.
While walking down the street, he stops by a bookseller stand on the sidewalk. There,
he spots and checks out the same novel that Sara showed him many years ago, but is disappointed to
find no writing inside and walks away. Coincidentally, on that same night, Sara,
who had since relocated to San Francisco, is proposed to by her long-time boyfriend.
She awkwardly accepts his proposal as he excitedly places a ring on her finger.
The next morning, Jonathan is haunted throughout the day, by ghosts of the past as he runs into
multiple women named Sara. Thus, reminding him of that short but magical night he had years ago. He
takes it as a sign from the universe, asking him to search for her one last time. Hence, he quickly
heads over to Dean's office to enlist his help. Later that night, Jonathan returns home to find
his fiancée decluttering his closet in preparation for their honeymoon.
While going through the pile of clothes, he finds one hand of the gloves he and Sara got from the
department store some years back, and for the first time ever, he looks inside it and is
shocked to find a piece of paper there. He unwraps the crumbled paper and discovers it to be an old
receipt that contains an account number. He takes the receipt and rushes to the store,
in a bid to trace Sara using the newly obtained account number. On arrival, Jonathan repeatedly
pleads with a salesman to check their records for her full name or contact details. The employee
is initially reluctant but only agrees to search her up on the system, if Jonathan
buys a bunch of clothes from the store. Desperate Jonathan obliges but becomes furious,
when the personnel ultimately checks the system and discovers that the account is closed.
Sympathetic towards his plight, the salesman volunteers to search for her details at their
storage unit, which houses hard copies of every account ever made with them.
Dean tags along and helps in searching the storage unit for her files. After a long search,
the group eventually finds it but can only make out the address on it, as the rest of the writings
appear smudged. They write down the address and immediately head over to the leasing company
incharge of the apartment, for more leads. Meanwhile, over at San Francisco,
Sara spends her day reminiscing on the spellbinding night she had with Jonathan
many years ago. She eventually decides to take a trip to New York to search for him,
in a quest to find closure. She tells her fiancé that she'd be going on a trip to the busy city,
while keeping the reason for her travel as vague as possible, and also invites
her best friend, Eve to tag along. On arriving in New York, the two friends
lodge in a hotel and go on to explore the city with hopes of running into Jonathan.
After a long day of futilely running around town, the duo settles for a meal at Serendipity.
While enjoying their meal, Eve convinces Sara to give up on finding Jonathan,
stating that life is much more than chasing baseless signs in hopes of finding some magical
ending. A downcast Sara takes the advice as a wake-up call and agrees to drop the quest.
The duo proceeds to leave the store as Eve grabs her change from atop the diner table.
However, unbeknownst to Sara, the exact bill Eve picked up, was the same one
from years ago with Jonathan's number. The ladies make it to the sidewalk and enter
a cab back to their hotel. Unluckily, Jonathan and Dean, who are still chasing their lead arrive
at the exact location mere moments after the cab leaves. They run into yet another dead end
which leaves Jonathan feeling disappointed. A depleted Jonathan, who spent the entire day
chasing dead-end leads, gives up his search and resigns to marry Halley as he heads to the hotel,
where they scheduled their wedding rehearsal. During the rehearsal dinner, Jonathan appears
distant and borderline lackadaisical throughout the event, much to Halley's dismay. After the
service, she confronts him about it and asks that he put whatever is troubling his mind to rest.
Wanting to please her, he accepts and apologizes for his recent behavior.
After resolving their light squabble, Halley hands him his wedding present.
Curious Jonathan enthusiastically opens it, and is shocked to see a copy of the novel
Sara showed him on that night, many years ago. Halley explains that she always saw him check out
that book in every store they went to. Hence, she decided to get a first edition copy for him as a
gift. A teary-eyed Jonathan opens the book, and receives the shock of his life on seeing Sara's
name and number on the novel's first page. He quickly sprints out of the building and
meets up with Dean, who is waiting outside to accompany the former to his bachelor party.
Jonathan immediately cancels the party, and quickly fills Dean in on the crazy
coincidence which just happened. An astonished Dean eventually regains
his composure, and manages to get Sara's address in San Francisco, from a tech-savvy
coworker who finds her contact info. The duo immediately catches the first flight they can
to San Francisco, hoping to get the chance to meet her before Jonathan's wedding tomorrow.
On getting to the address, they spot Sara's sister and her boyfriend having romantic moments.
However, Jonathan confuses her for Sara and is left severely heartbroken. Deciding that
pursuing her any further is useless, Jonathan heads back to New York for his wedding.
Meanwhile, the following morning, Sara gets on a plane heading back to San Francisco.
On the aircraft, she realizes that she mistakenly switched purses with Eve.
On checking the contents of the purse, she finds Jonathan's full name and number are
on one of the dollar bills in the purse. Seeing this, she races out of the aircraft
and quickly enters a cab to get to Jonathan, whose address she found via his phone number.
On getting to his apartment complex, she learns of his wedding, scheduled to hold that same morning.
Now convinced that they are destined to be together, Sara runs to the wedding location,
hoping to get there in time. However, on arriving, she finds the janitor
packing up the chairs. Thinking the wedding was already concluded, she instantly feels downcast.
But this is short-lived as the janitor soon informs her that the wedding never held,
as Jonathan called it off early that morning. A relieved Sara returns to her hotel room and
says farewell to Eve, who was returning to San Francisco that afternoon.
Meanwhile, Dean tries his best to cheer Jonathan up, as the former delivers an inspirational speech
while they stroll around town. Later that evening, Jonathan heads out alone to the skating rink,
where he took Sara on that eventful night. He sits on the bench and finds a leather jacket
there before making his way to the rink and lying in the center of it,
under the blistering snow. Meanwhile, Sara, who also visited the rink earlier,
remembers that she dropped her jacket on the nearby bench, and heads there to retrieve it.
On arrival, she instantly spots Jonathan lying on the snow,
who also notices her approaching. He stands up and the two simultaneously walk towards each other.
The reunited couple reintroduces themselves, and the movie ends as they ultimately, share a kiss.