John Mayer was seen having dinner with Kiernan Shipka, 24, from Mad Men on Friday night.
The 46-year-old Gravity singer, who recently discussed his future plans, was seen with the young actress outside the upscale San Vicente Bungalows in West Hollywood.
For their evening out, Mayer wore a fashionable black blazer adorned with palm patterns and vibrant yellow flowers.
The duo, who seemingly arrived at the members-only club separately, seemed to be in high spirits as they waited for the valet.
Kiernan looked glowing in a plain black blouse, and flashed a smile before getting into her vehicle.
The duo, who have a 23-year age difference, have been the focus of on-and-off romance rumors since 2022.
They’ve been seen on various low-key dates across Southern California over the years.
Earlier this year, Mayer and Shipka were seen together on a trip to Tokyo, Japan.
This recent sighting follows John’s statement six months ago on Kelly Rizzo’s Comfort Food podcast, where he said he “absolutely” wants “to get married.”
“People don't think I want to be married. I absolutely want to be married,” he told the host, adding, “You know the secret, which is that I'm actually fairly well-adjusted.”
“And I so badly want to get married if only for my wife to just know in her heart, like, ‘John will know what to do,’” he explained.
The multihyphenate further explained that he has a “reliability kink,” where he enjoys having his partners rely on him.
He added: “I just think that level of being relied on is the hottest thing in the world to me. ‘If my husband was here, he would know what to do. Call John. Call my husband.’”
“You're a full grown-up when this is your romantic fantasy. You're a fully fledged grown-up,” he concluded.
Throughout the years, John has famously dated A-list celebrities including Jessica Simpson, Katy Perry, and Taylor Swift.
Prior to dating the singer, Kiernan was most recently associated with filmmaker Christian Coppola, who is connected to The Godfather director Francis Ford Coppola and Priscilla filmmaker Sofia Coppola.
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