Sylvia and Will, once inseparable best friends, had shared countless memories together. She had even stood by his side as his maid of honour on his wedding day, a testament to their enduring bond. Despite the cliched predictions of a romantic entanglement, they had somehow managed to keep their friendship pure and unwavering for years.
However, when Sylvia attempted to warn Will about his wife, Audrey, their once-solid friendship crumbled, and they didn't speak to each other for five long years.
Now, in the present day, Audrey and Will have parted ways, and Sylvia finds the courage to call him for a coffee. Despite knowing about their separation, she refrains from disclosing it as the reason for their meeting.
The reunion is fraught with awkward silence and a palpable sense of lost connection. It's evident that Will doesn't want to be there, and the unique chemistry they once shared seems to have vanished. When Will inquiries about Sylvia's work, she deflects the conversation by showing him a picture of her family, only to quickly backtrack and reveal that she's actually unemployed.
Her embarrassment is fleeting as Will abruptly ends the meeting by inviting Sylvia to a party he's hosting at his bar. His friends - Omar, Andie, and Reggie - are skeptical of Sylvia's sudden reappearance in Will's life, but Will chalks it up to her attempts to rekindle their friendship.
The next day, Sylvia unburdens her heart to her close friend Katie, a fellow mother, while dropping off her kids. The women commiserate over the fact that men often lose interest in middle-aged women like them. Sylvia shares details about the party, and Katie encourages her to attend it together.
However, their excitement quickly turns to regret as they arrive at the party and find the atmosphere to be uncomfortable and unwelcoming. Before they can make their escape, Will spots Sylvia and approaches her. The women are forced to stay, and they soon find themselves in an uncomfortable situation when Andy treats Sylvia rudely, apparently assuming that she's trying to make a move on Will.
The women soon decide to leave the party and lament the lack of male friends in their current stage of life. As they walk away, they chance upon Will arguing heatedly with Audrey outside the bar. It's clear that Will is furious with her for bringing a date to the party.
After Audrey storms off, Sylvia opts to stay and comfort her old friend. Over drinks at his bar, Will confesses to Sylvia that Audrey lost interest in him as she climbed the social ladder as a successful art dealer. He admits to cheating on her with a stranger, and that was the end of their marriage.
A drunken Sylvia decides to recreate their old days and becomes Will's "wing-lass," determined to help him land a new woman. However, their efforts are far from successful, and Sylvia wonders what happened to the charming and confident "player Will" who once drew the attention of countless women.
As they flip through an old photo album, they stumble upon a picture of Will wearing a chai necklace that was once his lucky charm. He reveals that he no longer has it, and Sylvia, filled with nostalgia, excitedly takes him to a store to buy a new one.
In the bustling shop, Will's eyes caught a glimpse of a necklace adorned with a "W", dangling gracefully around the neck of a majestic Doberman. The owner, with a wink and a sly smile, offered it to them for a mere $50, but with a curious request: to remove it from the dog's neck. After a deft maneuver, they succeeded, and Will proudly wore the necklace around his own neck, letting it accompany him throughout the evening.
Later, they indulged in weed-infused gummies and a sumptuous dinner, using the city as their playground to rekindle their friendship. The night seemed to be drawing to a perfect close for Sylvia, until a careless remark about Will's divorce marred the harmony. Before she could even finish her sentence, Will's expression darkened. He was both perplexed and offended, mistaking Sylvia's concern as pity.
The friendly exchange quickly deteriorated into a heated argument, with hurtful words flying between them. Will was accused of having a double standard, refusing to sever his friendship with Andy despite hating Audrey. Despite their acrimonious parting, Sylvia couldn't help but try Will's odd trick in bed with her husband, Charlie. When it failed to produce the desired effect, she reluctantly texted Will, and their conversation grew increasingly ominous as something seemed to be brewing, ready to "give way."
