The Break-Up(2006)

Brook (Jennifer Aniston) dates other guys to make Gary (Vince Vaughn) jealous.  It doesn’t work.  By the time he realizes that she’s the one for him, it’s too late because she tells him she doesn’t feel the same way.  They sell the condo.  He expands his family business and she travels. 

Months later, they run into each other and greet each other but gaze at each other like they “miss” each other.  They say hello, compliment each other and agree to not let so much time pass on before keeping in touch.  As they walk in opposite directions, they both look back.  Gary winks at Brook and she smiles back