About This Script
Two couples. Two Matts. Two Jens. One ring. Old Matt (38) has been with Old Jen for nine years and has no intention of proposing — he’s a flannel-wearing, Cubs-loving Chicago guy who works his family’s bar across from Wrigley and believes life ends the moment you say I do. Young Matt (27) is a rising lawyer who has been dating Young Jen for six months and believes life ends if you wait too long. He drops his grandmother’s heirloom ring during a botched jumbotron proposal. Old Matt picks it up. The camera finds Old Matt on one knee. Fifty thousand people watch Old Jen say yes.
Now Old Matt is engaged to a woman he loves but isn’t ready to marry, Young Matt needs his grandmother’s ring back, and both men are completely in over their heads. Their plan: Young Jen — a wedding planner — will handle Old Matt and Old Jen’s wedding while Old Matt plays Groomzilla to drag out the planning indefinitely. In return, Old Matt will use a family connection to land Young Jen the career-making client she needs to finally say yes to Young Matt. Two men. Opposite problems. One spectacularly bad plan.
Set against the backdrop of Wrigley Field, O’Connor’s Pub, and the Chicago lakefront, The Engage-meant is a double love story about four people who all want the same thing — to get it right — and are each going about it completely wrong.
Theme
“Loving someone and being loved back is the most amazing experience. Don’t run from it — run to it.”
Four Sides of the Same Equation
Every character represents a different fear of commitment.
Old Matt, 38 — Cubs fan, family bar owner, nine years with Jen. Believes marriage ends dreams. His own father gave up pro baseball when Old Matt was born — or so he thinks.
Young Matt, 27 — Lawyer, six months in, already has grandma’s ring. His father died at 35. He’s in a race against a clock only he can hear.
Old Jen, 38 — Marine biologist at the Shedd Aquarium. Warm, patient, quietly running out of time. Everyone tells her to leave. She can’t.
Young Jen, 27 — Wedding planner with a checklist for love. Her parents’ divorce taught her that commitment is a promise men break. She won’t rely on anyone.
The Inciting Incident
Chicago Cubs playoff game. Young Matt drops the ring — it rolls three rows down and lands under Old Matt’s seat. Old Matt picks it up. The jumbotron finds him on one knee. Fifty thousand people see Old Jen say yes. Young Matt watches from four rows up.
Why It Sells
- High-concept premise pitches itself in one sentence — no setup required
- Double love story with four fully realized characters — strong ensemble casting potential
- Wrigley Field / Chicago setting is visually iconic and commercially distinctive
- Commitment-phobia as theme is universally relatable — broad demographic appeal
Script Details
Format: Feature Film
Genre: Romantic Comedy
Setting: Chicago — Wrigley Field, O’Connor’s Pub, Lincoln Park, the Shedd Aquarium
Target: Wide release / Studio
Comps: He’s Just Not That Into You · The Proposal
Status: Treatment