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Before John Lennon began dating his first wife, Cynthia, his girlfriend was Thelma Pickles, one of his art school classmates. They dated for a time before she ended their romance. She said that even if they had dated for longer, she wouldn’t have wanted to marry the future Beatle. Pickles said Lennon was difficult to date, and she described him as a “bum.”

John Lennon wears sunglasses and carries a bag over his shoulder.
John Lennon | Vinnie Zuffante/Michael Ochs Archives/Getty Images

John Lennon met his first girlfriend at art school

Lennon and Pickles met at the Liverpool College of Art, where they were both students. As with his future wife, Cynthia, she didn’t like him at first.

“My first impression of John was that he was a smartarse,” Pickles told The Guardian. “I was 16; a friend introduced us at Liverpool College of Art when we were waiting to register. There was a radio host at the time called Wilfred Pickles whose catchphrase was ‘Give them the money, Mabel!’ When John heard my name he asked, ‘Any relation to Wilfred?’ which I was sick of hearing.”

A black and white picture of John Lennon walking outside in a group of people.
John Lennon | Unknown/Mirrorpix/Mirrorpix via Getty Images

Eventually, though, she warmed to him when he showed her a different side of himself in private.

“When we were alone together he was really soft, thoughtful and generous-spirited,” she explained. “Clearly his mother’s death had disturbed him. We both felt that we’d been dealt a raw deal in our family circumstances, which drew us together.”

She gave a brutally honest assessment of the musician

Pickles said she and Lennon spent a great deal of time out together, and she said he was always borrowing money from people.

“John never had any money,” she said, per the book The Beatles: The Authorized Biography by Hunter Davies. “He was a real bum, borrowing from everybody all the time, getting people to buy him chips or drinks, or cadging ciggies. He must still owe people pounds. But he has a sort of magnetic personality and could always get money out of people.”

Pickles said that Lennon always had to borrow money because his aunt gave him a limited allowance.

“She wouldn’t let him go anywhere and only gave him half a crown a day to spend,” she explained. “She was overstrict. We spent hours drinking, or just standing around in the Crack [a pub next to College]. But John couldn’t do much drinking on half a crown, could he?”

John Lennon’s girlfriend said she wouldn’t have wanted to marry him

After they broke up, Pickles said she missed the closeness of their relationship, but she didn’t spend much time mourning after the split. She had no regrets about ending their romance, even after Lennon rose to fame in The Beatles.

A black and white picture of John Lennon playing guitar.
John Lennon | Keystone-France/Gamma-Keystone via Getty Images

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“I’ve never wondered what might have been,” she said. “It sounds disingenuous, but I wouldn’t like to have been married to John — that would be quite a gargantuan task! He would’ve been 70 next year and I just cannot imagine a 70-year-old John Lennon. I’d be fearful that the fire would’ve gone out.”