The Family Man (2000)

An investment broker gets a chance to see what life would have been like if he stayed with the girl when he was younger instead of pursuing his dreams. He starts to second guess his life choices.

I give this movie a 4.5 out of 5.

Starring Nicolas Cage (Face/Off, Leaving Las Vegas, The Rock, Next) as Jack Campbell, Tea Leoni (Jurassic Park III, Deep Impact, Spanglish, Madam Secretary) as Kate Reynolds, Don Cheadle (Crash, The Guard, Hotel Rwanda, Traffic) as Cash, Jeremy Piven (Serendipity, Entourage, Grosse Point Blank, Say Anything...) as Arnie, Saul Rubinek (Unforgiven, True Romance, Polina, I Am Normal) as Alan Mintz, Josef Sommer (Strange Days, Dirty Harry, Witness, The Other Guys) as Peter Lassiter, Makenzie Vega (Sin City, In the Land of Women, Saw, Tomboy) as Annie Campbell, introducing Jake Milkovich (JAG) as Jash Campbell, introducing Ryan Milkovich as Josh Campbell, Lisa Thornhill (After the Sunset, Veronica Mars, Rush Hour 3, The Perfect One) as Evelyn Thompson, the late Harve Presnell [1933-2009] (Fargo, Saving Private Ryan, Paint Your Wagon, Love Ranch) as Big Ed, Mary Beth Hurt (Lady in the Water, The Age of Innocense, The Exorcism of Emily Rose, The World According to Garp) as Adelle, Amber Valletta (Gamer, Hitch, Transporter 2, Dead Silence) as Paula, the late Francine York [1936-2017] (The Doll Squad, The Under Achievers, Ten Violent Women: Part Two, Star Trek: Progeny) as Lorraine and Ruth Williamson (The Producers, Legally Blonde 2: Red, White & Blonde; Star Trek: Enterprise, The Watcher) as Betty Peterson.

https://www.imdb.com/title/tt0218967/