As Annie and Jake return to their apartment in Chicago from a romantic two-week island holiday, they're about to reach a tricky-to-negotiate relationship crossroads.

Casey WilsonAnnie

Ken MarinoJake

John GemberlingGil

Sarah WrightDennah

Tymberlee HillKay

Tim MeadowsKevin One

Dan BucatinskyKevin Two

Deanna ChengWaitress

JoBeth WilliamsMyrna

Walter TabayoyongJamie The Singing Waiter

Jessica St. ClairJulie

Becky FeldmanCustomer

Colby SeveranceBoy

Mallory LowSinging Waiter number 4

Jerry O'ConnellDaniel

Riley LioQuinn

Leslie David BakerJake’s Boss

Danielle SchneiderCassie

Kimmy RobertsonHostess

Steve WiebeDaniel

Mark ProkschChad

Mike HagertyOfficer Stackhouse

Nick PeineSinging Waiter

Malcolm DevineSinging Waiter

Gabrielle SanalitroSinging Waiter

Jet JurgensmeyerMason

Roger MarksMan

Mike O'GormanLiam

Hana Mae LeeFantasia Yang

Raff AnoushianMaintenance Man

Tracy MeyerWaiter

Wesley ScottMounted Cop

Neil CaseyFred

Corey Allen KotlerMover

Alden RaySecurity Guard

Michael J. SielaffSecurity Guard

Mo GaffneyDawn

Andrea BordeauxWaitress

Cazzey Louis CereghinoBiker

Michael GainesGuy

Nat FaxonScooby

Jordan FullerBoy

Paul YenLo Fang

Bernardo VerdugoBusboy

Lawrence Wayne CurryCheering Waiter

Jason GallowayCheering Waiter

Tamika Katon-DonegalCheering Waiter

Chelsea LevyYoung Annie

Rob HuebelWes

Briana VenskusLinda

John Ross BowieWhat's-His-Name

Crista FlanaganLibby

Vinoj ZachariaWaiter

Kevin AshworthMike Berman

Travis GubaSecurity Guard

Kristen LapariMeredith

Jackie MahReceptionist

Rob RiggleGary Thick

Natasha LeggeroLaguna Matata

Tyler PeckGuy

Steve LittleGut Boy

Brandon JohnsonMatthew

Mike RadGus

Alfred Rubin ThompsonEdgar

Paul ChiricoJurgen

Ana OrtizHailey

Mel CowanAtlas

Thomas W. AshworthGeorge

Gregory A. ThompsonBenny

Albert MalafronteOld Board Member

Matthew Del NegroPeter

Brad GrunbergLomax

John MaholmFireman

Greg Romero WilsonLester

Marcus FolmarGordy

Bryan CoffeeRestaurant Employee

Michaela WatkinsJanet

Sam LloydHank

Elizabeth HoBrianna

Matt McConkeyHR Guy

Silvio CuadraCo-Worker

Julie BristerCo-Worker

Brennan FeonixCo-Worker

Christopher Charles BakerWaiter