BEN AFFLECK — if Brad was too good, Ben Affleck wasn’t good enough—yet. The actor, a wunderkind Oscar winner for co-writing ‘Good Will Hunting’ with buddy Matt Damon, met Paltrow at a Weinstein-hosted dinner in 1997 before they both appeared in 1998’s Shakespeare in Love. They had great chemistry, but by the time Paltrow was vacuuming up awards en route to winning her Oscar in 1999, she and Affleck had dwindled to friends status. They would then rekindle briefly in late 1999 when they co-starred in Bounce, and end up the kind of friends who stay at each other’s house on occasion.
BRAD PITT — the one that got away. For both, perhaps? “I messed that up, Brad,” Paltrow said on the Girlboss Radio podcast when host Sophia Amoruso mentioned Gwyneth’s great love of the mid-’to-late-90s, whom she met in 1994 on the set of the thriller ‘Se7en’, playing his ill-fated wife. When he won a Golden Globe for ‘12 Monkeys’ in 1996, Pitt’s final thank you was reserved for “especially the love o’ my life, my angel, Gwyneth Paltrow.” They got engaged, they even got matching haircuts, but then they broke up in June 1997. Paltrow has been relentless in blaming herself for the demise of their relationship, telling Diane Sawyer in 2003, “I’m so lucky that I spent time with Brad, somebody who was such a good person!”
BRYAN ADAMS — in August 2002, with the nation still reeling from her comment, London’s Evening Standard pegged the Canadian singer as another of the intrepid sorts who dared to ask Gwyneth out.
LUKE WILSON — unlike Margot and Richie Tenenbaum, Luke and Gywneth didn’t have to keep their feelings confined to a tent in the attic. The actors dated for about a year after they connected while making ‘The Royal Tenenbaums’, a seemingly drama-free affair. In 2001, in an interview published while she was rumoured to be dating Wilson, Paltrow told Harper’s Bazaar about her ideal man: “He’s tall and thin, but muscular, to start with the superficial. A gentleman.”
SCOTT SPEEDMAN — Paltrow was briefly linked to her Duets co-star—who was cast as a replacement for Brad Pitt in the 2000 ensemble drama, which was directed by Bruce Paltrow and featured Gwyneth’s cover of “Cruisin’” with Huey Lewis.
Published in Daily Times, November 27th 2017.