In a series of outings, the couple — who wed in 1997 — were snapped by photographers taking in the sights of the Big Apple.
They were first seen in the daytime, strolling the streets in downtown Manhattan as they headed to an art gallery where they met up with Leonardo DiCaprio and his father.
For the trip, Stallone, 76, sported an all-black ensemble while Flavin, 54, embraced the fall season in a beige long-sleeved turtleneck and white jeans. She carried a blush purse and accessorized her look with gold earrings.
Both were notably wearing their wedding rings.
The Rocky actor and his wife changed their clothes for a date night later in the evening, as they stepped out for dinner at the Polo Bar.
James Devaney/GC Images
Stallone looked sharp in a navy suit with matching navy button-down shirt.
Flavin wore an off-the shoulder, chic knit black dress. She paired the LBD with a Saint Laurent clutch, black pumps and a statement Balenciaga belt.
James Devaney/GC Images
On Sept. 30, PEOPLE confirmed that Flavin and Stallone reconciled one month after she filed for divorce on Aug. 19 after 25 years of marriage.
"They've decided to let it ride again," a source told PEOPLE about their decision. "They just decided to reverse course and try again."
In her divorce filing, Flavin had alleged that the actor "engaged in the intentional dissipation, depletion and/or waste of marital assets which has had an adverse economic impact on the marital estate," which he denied.
Meanwhile, Stallone's anticipated mob saga Tulsa King debuts on the streaming service Nov. 13.
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Despite their late-summer disagreement that led to the divorce filing, the Rambo star and his wife previously took time to lovingly acknowledge their 25th wedding anniversary.
"Happy 25th anniversary to my amazing wife," Stallone captioned a photo carousel of the pair in an Instagram post. "There is not enough words to describe what this incredibly selfless dedicated, patient, woman has meant to our lives and I only wish they could be another 25! Thank you sweetheart!"
Flavin wrote alongside her own snapshot collection, "Happy 25th wedding anniversary to us! 🥰 ❤️❤️ ❤️ Thank you for always keeping me laughing, loving and protecting our beautiful family!"
She concluded, "Our marriage keeps getting better every year! I can't wait to spend the rest of our lives together! 🥰 ❤️ ❤️ ❤️."