How I Ruined my Best Friend’s Wedding is More Than a Rom-Com!

by Gordon Shelly

Nick Kempton, who recently had two screenplays named to the “Best Screenplay Category” as Finalists in the 2020 SoCal Film Awards, was able to take some time away from his busy schedule and discuss his award-winning feature screenplay, How I Ruined my Best Friend’s Wedding.

How I Ruined my Best Friend’s Wedding tells the story of friends Mary and Sam in a romantic comedy finding similarities with movies such as When Harry Met Sally and There’s something about Mary. Of course, Kempton is careful to make this story and his character’s journeys their own, and while there might be some common themes of the genre, the story is, indeed, uniquely its own.

The tale opens with Mary inviting Sam to serve as an usher at her wedding, which he, her best friend, wasn’t even invited to attend except as a plus-one guest. With reticence, he accepts.  Soon, we’re introduced to a variety of colorful characters and through a series of unexpected events, Sam ends up much more involved with the wedding than he had planned. Initially, an uninvited guest, then a key cog in the marriage machine.

As the story progresses, Sam realizes the truth of his feelings for Mary as more than a friend, and he sets out to live up to the screenplay’s title by “ruining” her wedding.

The story plays on some tried and true themes but maintains a freshness as we journey with Sam and Mary and many of the wedding guests through a comedic and heartfelt story, but no spoilers here.

Writer Nick Kempton has previously told INFLUX a bit about his process and where his ideas come from. We asked him, in particular about How I Ruined my Best Friend’s Wedding.

NICK: How I Ruined My Best Friend’s Wedding was conceived as an epic, dramatic, ensemble musical, like the baby of Love, Actually and Moulin Rouge … but better! A bit ambitious, to say the least. I ran into several roadblocks writing this, so I broke it down to the story of what I wanted to tell and how I wanted to tell it. I tried to keep some elements (the ensemble stayed, the musical dropped) and stuck with what I was comfortable writing (comedies, not musicals … well, not yet).

INFLUX: Ambitious indeed! How long did it take you to write this screenplay?

How I Ruined My Best Friend’s Wedding took several years…I started it back in 2013 and didn’t have a readable first draft until maybe 2018? There were several stalling points and stops/starts.

INFLUX: Are your characters entirely fictional or are they based on real people? Care to elaborate?

NICK: Some of them are based on real people…Sam (from How I Ruined My Best Friend’s Wedding) is loosely based on myself, though I haven’t (deliberately) tried to ruin someone’s wedding! Jacob (from How I Ruined My Best Friend’s Wedding) is based on a friend of mine from college; a mutual friend read the screenplay and asked me if Jacob was supposed to be [said person], which made me feel good about capturing his personality.

INFLUX: If How I Ruined my Best Friend’s Wedding were to get produced, who would be on your short list of actors in the main roles in an ideal world?

Good question! I’d love John Boyega to play Sam (he’s got wonderful comedy skills), Vincent Rodriguez III for Dylan (I think he can play the uncomfortable-but-slowly-loosens-up character Dylan becomes), Billie Lourd for Mary (she’d be able to keep the Mary’s exasperation with the hijinks humorous), and Hailee Steinfeld as Kat (she’s a master of the take-no-prisoners attitude and the comedy).

INFLUX: What’s next for Nick Kempton?

Hopefully, more things like this! I’ve got two scripts that I’m working on right now: one is with some friends about our experiences during our study abroad semester in college, and the various misadventures and hijinks that occurred (some names may have been changed to protect the innocent – and the guilty); the other is a medieval fantasy with mages, queens, diabolical plots, thrilling heroics, and epic duels. So, fun things.

INFLUX: Where/how can we follow and keep up with what you’re doing? (Social media, website, etc.):

Follow me on Twitter: @SirNick1942 or on Instagram: @GrumpyOldMan421. Thanks so much!

Read Part I of this Interview Here!