It appears we’re in for another round of speculation in the celebrity dating world as John Mayer is once again fueling rumors of a romantic connection, this time with actress Kiernan Shipka. At 46, Mayer’s recent appearances with the 24-year-old Shipka have raised eyebrows and ignited discussions online, echoing sentiments previously voiced, perhaps most notably by Taylor Swift in her song “Dear John.”
The pair have been observed leaving the same locations on multiple occasions over the past month, although seemingly attempting to maintain separate exits. Most recently, on a Friday evening, paparazzi captured images of both Mayer and Shipka outside the San Vicente Bungalows in West Hollywood, an exclusive, members-only establishment, as reported by the Daily Mail.
John Mayer at an event, looking towards the camera with a blurred background of people.
The unusual nature of this potential pairing hasn’t escaped public notice. Many remember Shipka’s portrayal of Sally Draper in Mad Men from a young age. Adding to the context, it’s noteworthy that Shipka was just a toddler when Mayer released his debut album Room for Squares. This significant age difference has become a central point of discussion surrounding these dating rumors.
Kiernan Shipka posing for a photo in a stylish outfit against a plain backdrop.
Interestingly, this isn’t the first time Mayer and Shipka have been romantically linked. Rumors of a possible relationship between them have circulated for several years. Back in 2022, Entertainment Tonight reported on a dinner outing between Mayer and Shipka at Giorgio Baldi in Santa Monica, suggesting a romantic atmosphere. Sources at the time indicated that Mayer may have serenaded Shipka and that they appeared to be very interested in each other’s company. While they departed separately, an insider account detailed a clandestine car switch, with Shipka reportedly joining Mayer’s SUV before being driven home, adding a layer of intrigue to their interactions.
Earlier in February 2022, photographic evidence emerged of Mayer and Shipka embracing at a bar, further fueling the dating speculation.
Kiernan Shipka as Sally Draper in Mad Men, sitting at a table with a serious expression during a scene.
Adding another layer to the rumor mill, Deuxmoi, an Instagram-based celebrity gossip account, shared tips suggesting Shipka’s attendance at Mayer’s concerts in 2023. An anonymous source even referred to her as his “special friend,” although these claims remain unverified. One tip described a recurring pattern of Shipka being discreetly seated near the side stage shortly after Mayer began his performances, hinting at a consistent arrangement throughout his tour.
As of now, neither Mayer nor Shipka have officially addressed these dating rumors. However, the continued sightings are likely to keep the speculation alive. Meanwhile, reactions across social media platforms like X (formerly Twitter) reveal a strong undercurrent of concern, with many users humorously and pointedly urging Shipka to “RUN,” reflecting a widespread sentiment of caution regarding this potential pairing.
ill get older but your lovers stay my age
— 𝙚𝙡𝙚𝙣𝙖. (@hellxxn) July 21, 2024
Feature Image: Getty
