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Red Sox fan proposal gets really awkward: ‘I don’t know’

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Last updated: May 4, 2026 2:08 pm
amedpost
Published: May 4, 2026
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Not even a classic Fenway Park proposal can go right for the Red Sox and their fans.

During the fifth inning of a game against the Astros, a couple was shown on the jumbotron with the words “Serah Linn, will you marry me?”

Yet, the woman in the video didn’t look at the screen once and the body language between the couple couldn’t have been worse.

As the woman was asked, she seemed to say “I don’t know,” per the Boston Herald’s reporter Gabrielle Starr.


One of the most awkward proposals occurred on Sunday at Fenway Park.
One of the most awkward proposals occurred on Sunday at Fenway Park.

Still, the man went in to kiss the woman and afterward she leaned into him to say something as “Congratualtions Douglas and Serah!” came on the jumbotron.

The two continued to awkwardly talk on camera while the man pointed at the camera and screen before the feed cuts off.

They just showed a proposal on the Fenway videoboard in between the top and bottom of the fifth, and it looked like the woman said, “I don’t know.”

— Gabrielle Starr (@gfstarr1) May 3, 2026

The moment grabbed the attention of Linda Henry, wife of owner John Henry and CEO of the Boston Globe and Boston.com, as she recorded the whole awkward moment on her Instagram story.

“Quieter reaction on this one….” she wrote followed by, “Congratulations Serah and Douglas.”

The moment didn’t seem to go as planned at all.

The Red Sox lost 3-1 in 10 innings on Sunday to drop two of three to Houston as the bad vibes circulate around the team.

Amid Boston’s 13-21 start, chief baseball officer Craig Breslow and Henry have come under fire from the fans.

The proposal comes on the heels of the team firing manager Alex Cora along with other coaching staff, and a plane flying over Fenway Park during batting practice with a banner that read: “FIRE CRAIG! SELL THE TEAM!”

Tensions in the clubhouse are high and players have even started to criticize each other after the most recent loss.



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