The encounter, as recalled by E Jean Carroll, was friendly at first.
Ms Carroll, then a magazine feature writer and TV host, bumped into Donald Trump in the upmarket New York department store Bergdorf Goodman.
As Ms Carroll wrote in her 2019 memoir What Do We Need Men For?, he recognised her as “that advice lady”. She knew him as “that real-estate tycoon”.
Mr Trump supposedly told her that he was there to buy a gift for “a girl”, and asked for help to choose an appropriate item.
She placed the incident in either late 1995 or early 1996, when the future president was married to Marla Maples.
The pair made their way to the lingerie section, where Mr Trump suggested that she try on a lace bodysuit.
She claims jokingly said that he should try it on instead.
As they reached the dressing rooms, Ms Carroll alleges that Mr Trump shoved her against a wall, put his hands underneath her dress and pulled down her tights.
He then unzips his pants, and “forcing his fingers around my private area, thrusts his penis halfway — or completely, I’m not certain — inside me”, she wrote.
A “colossal struggle” ensued, she said, and Ms Carroll eventually pushed him away and ran out of the dressing room. The episode was over in under three minutes, she wrote.
After the allegations were first made in a book excerpt in New York magazine in June 2019, Mr Trump angrily denied it.
"I've never met this person in my life. She is trying to sell a new book — that should indicate her motivation. It should be sold in the fiction section,” he said in an official White House statement that month.
Then days later in an interview in the Oval Office with The Hill, Mr Trump went even further.
“I’ll say it with great respect: Number one, she’s not my type. Number two, it never happened. It never happened, OK?”
Ms Carroll then filed a defamation lawsuit against Mr Trump alleging he had damaged her reputation, substantially harmed her professionally, and caused emotional pain.
After writing her Ask E Jean column for Elle magazine for nearly 30 years, the magazine terminated her contract abruptly in December that year. The magazine denied it was related to Ms Carroll’s allegations.
In 2022, New York passed the Adult Survivors Act which allowed adult sexual assault survivors one year to sue their alleged abusers.
Ms Carroll filed a second lawsuit against Mr Trump for rape and for additional alleged defamatory statements made by him in October 2022 where he called her a “complete con job”.
In a court filing earlier this year, Judge Lewis Kaplan wrote that the central issue in both cases is the same — whether Mr Trump raped Ms Carroll.
“If he did not, then Ms Carroll’s sexual assault claim ... and her libel claims in both cases likely would fail.
“If he did, then little would remain in either case except perhaps a few minor issues related to Mr Trump’s statements and determination of damages.”
In addition to Ms Carroll herself, her attorneys plan to call several friends that she spoke to about the allegations at the time, former White House press secretary Stephanie Grisham and Ashlee Humphreys, a Professor at Medill School of Journalism, Northwestern University.
Ms Carroll’s attorney Roberta Kaplan said they tried for three years to obtain Mr Trump’s DNA sample to compare it with stains found on the dress she was wearing on the day.
After refusing to provide a sample, Mr Trump’s attorneys then made an 11th-hour offer to do so earlier this year. Judge Kaplan rejected the offer.
For the defence, Mr Trump’s attorneys have listed him, CNN anchor Anderson Cooper and several others on their list of potential witnesses.
Mr Trump has not confirmed whether he will attend the trial, which begins in the US District Court in Lower Manhattan on Tuesday, 25 April.
As the case is being tried in civil court, the jury will likely be asked to find whether there is “a preponderance of evidence” to prove Ms Carroll’s claims, rather than the criminal standard of “beyond reasonable doubt”.
More than two dozen women have accused Mr Trump of sexual assault.
