Posted in Film, Nonfiction

My Grandmother’s Date with Clint Eastwood: The Untold True Story!


My grandmother Barbara Krueger went on a date with Clint Eastwood when she was a teenager. Yep, it was the legendary story I could never get enough of.

She told me that she and Clint jumped on a streetcar together, went to a movie (she never remembered what it was), and stopped off at an ice cream parlor before heading home. Her parents Weldon and Lolita were best friends with Clint’s parents, and so Barbara saw Clint from time to time at social gatherings and local town events. No sparks flew between them on their date, a few years later she married my grandfather Ralph, and the rest, as they say, is history.

But is this the whole story?

Maybe Barbara was Clint’s one lost love, the girl who got away before he could tell her how much she meant to him. Maybe he told her that one warm summer night that he wanted to go steady, maybe even steal a kiss from her, before they parted ways forever. He was fifty years away from romancing Meryl Streep in The Bridges of Madison County, but on that night in 1945, Clint only had one luminous creature in his sights: Barbara.

He had stopped by every night that week, asking Barbara to go to the movies, but she kept saying no. She had homework and chores to do, by God. Besides, her sights were set on Chester Durst, the high school quarterback with the husky voice of a commercial voice-over artist. Clint rattled off various titles of new movies to see: Gaslight, with Ingrid Bergman, and Alfred Hitchcock’s Spellbound, also with Ingrid Bergman.

“Sounds like you want to go out with Ingrid,” Barbara said, talking to Clint from her upstairs bedroom window. “And sorry, but I’d rather go out with Gregory Peck, thank you very much.”

Clint shoved his fists against his sides and shouted, “Hey, now. I’m better looking than that old fart Gregory Peck!”

Barbara scoffed as she started shutting the window. “Of course you would say that. What do you think you are, a movie star?”

He called her the next day, and went to her doorstep the next night. He was only sixteen, but he felt a connection to Barbara that he couldn’t fully understand. Maybe it was the way she played hard to get. Maybe it was that she liked to talk back. Maybe it was that she was stunningly, unimaginably gorgeous that summer, so perfect in every way he could barely sleep at night.

Clint refused to take no for an answer, and finally, just to get him off her back, she agreed to go get ice cream on Saturday night, at a parlor called Freeze-In. She figured one hour would be enough, but Clint surprised her by taking the empty trolley two more stops to the town cinema, which was playing The Picture of Dorian Gray. A horror movie, the one genre Barbara detested and was still forbidden to watch, her mother forever traumatized that Barbara caught the end of Frankenstein on a late night double bill.

Clint assured her it was more of a drama than a horror film, so Barbara decided to allow his entertainment choice. Maybe she thought it would scare him enough to send him running out of the theater, allowing Barbara to enjoy a forbidden movie all by herself. He stayed for the whole show of course, putting his arm around her shoulder the minute a young Angela Lansbury showed up on screen, and Barbara slunk down in her seat, paying more attention to Clint’s wandering fingers than the movie. He tried to kiss her twice, once on her cheek and once on her neck, but both times she faked a cough and darted her head forward.

On the way home, Clint and Barbara still reeling from the last act twist of Dorian Gray, they stopped off at the local ice cream parlor, which was about to close. Barbara picked vanilla — fast, easy — but Clint took five minutes to decide, eventually settling on a double scoop of butter pecan and chocolate peanut butter, with hot fudge and whipped cream, no cherry.

Clint probably thought his order would impress her, but all she could do for the next twenty minutes was polish off her little cone and then watch him stuff his face until the store owner finally booted them out. He tried to kiss her one more time when they stopped at her front porch, but his mouth smelled too nutty, so she declined.

He asked her out a few more times that year, but eventually Clint set his eyes on a vivacious high school senior named Julia Swills, who agreed to be his girlfriend before the end of their first date. He still wanted Barbara, but he was over the rejection. It was time for him to move on.

After Clint left small town life for the bright lights in Hollywood, one might assume that he never saw Barbara again. As a matter of fact, they still saw each other often, all the way until the end of my grandmother’s life. In the early part of his career, after Sergio Leone’s Man with No Name trilogy but before his acclaimed directing career and the Dirty Harry movies, he attended a Christmas party at Barbara’s parents’ house, even proceeding to play guitar for everybody. Barbara watched from the big leather sofa, a grin on her face, her arm around her husband Ralph and her three young children. Clint was on his way to global success, with women flocking to him like those seagulls in The Birds, but he took the time to serenade Barbara all night, zoning out her family and focusing in on the face he fell in love with all those years ago.

Clint and Barbara saw each other less and less, but in the last two decades of my grandmother’s life, she took a yearly trip to the AT&T Celebrity Golf Tournament in Pebble Beach, California, where Clint always appeared for a few days on the links, sometimes with film actors like Samuel L. Jackson and Michael Douglas, other times with golf legends like Arnold Palmer and Tiger Woods. For many years she cornered him in parking lots to say a few fleeting words and take a picture, and remind Clint of her beauty that had never faded.

On her last trip to the tournament, I accompanied Barbara, still not believing that she ever knew Clint, still doubtful she ever went on a date with him, and so I watched in amazement when he locked his eyes on her on the ninth hole, shouted, “Barbara!” and gave my grandmother the biggest of hugs. They talked for five minutes. He asked about Weldon, about Lolita. And he asked about her, what she was doing, what her life was like all those years since their short but magical date. He hadn’t forgotten her, had always kept that luminous girl of his dreams at the back of his mind, memories of that one perfect night forever present inside his heart.

Seventy years have passed since their date in the ’40s. My grandmother is now gone, sadly, having passed away in 20125. But Clint Eastwood — four time Oscar winner and cinematic icon — is still here, and he still remembers, will always remember, until the day he dies. She, Barbara of course, will always be the one who got away.

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