Ivanka Trump had been speaking for less than five minutes on Tuesday before the jeers started coming from the audience.

Given the topic and venue, they seemed almost inevitable. At the invitation of German Chancellor Angela Merkel, the First Daughter of the United States had come to Berlin for a round-table discussion on the empowerment of women, a subject that was sure to clash with the sexist and vulgar remarks her father has made about women in the past.

Sure enough, when she referred to President Donald Trump as a “tremendous champion” of women’s rights, particularly the right to take paid leave after childbirth, a wave of titters and groans of derision spread through the hall at Berlin’s Hotel Intercontinental. The moderator, journalist Miriam Meckel, then interrupted Ivanka in order to grill her on her father’s controversial remarks about women.

The booing — and the line of questioning — quickly made headlines in the U.S., overshadowing the event and the circle of powerful women with whom Trump shared the stage in Berlin. Among them were Queen Maxima of the Netherlands, Christine Lagarde of the International Monetary Fund and Canadian Foreign Minister Chrystia Freeland. None however likely winced quite as hard as Merkel when the crowd began to turn against Trump.

For the German Chancellor, Ivanka’s visit was a crucial chance to form a bond with an Administration that has been cold toward Berlin from the start. During his campaign for the presidency, Trump repeatedly used Merkel as a rhetorical punching bag — calling her refugee policy a “catastrophic mistake” and accusing the Chancellor of “ruining Germany.”

Relations did not quickly improve after Trump’s election victory. Breaking with decades of diplomatic tradition, his transition team refused to let the State Department mediate contacts with foreign leaders. So Merkel’s office was forced to seek advice from Henry Kissinger, the German-born former U.S. Secretary of State, who advised the Chancellery to contact the Trump Administration through Ivanka’s husband, Jared Kushner. “This has been proven successful,” Merkel’s foreign policy adviser, Christoph Heusgen, told me at the time.

Kushner, who now holds the title of senior adviser to President Trump, then helped arrange Merkel’s first meeting last month with the Trump Administration in Washington, D.C. It did not go smoothly. While posing for a photo in the Oval Office, Merkel repeatedly asked Trump to shake her hand for the cameras, and the President did not respond. In what appeared to be another slight, the Chancellor was seated beside Ivanka during a summit with U.S. and German business leaders — an arrangement that got the White House accused of sexism.

But Merkel saw it as an opportunity. Perfectly aware of the outsize influence that both Kushner and Ivanka have over the U.S. President, the Chancellor extended an invitation to the First Daughter to join the panel at the W20 summit in Berlin, part of her program to advance women’s rights as Germany gets ready to host the G-20 summit of world leaders this summer.

Ivanka took the invitation seriously. On the eve of the Berlin meeting, she co-authored an op-ed in the Financial Times titled, “Investment in Women Unleashes Global Gains,” which called for legislative reforms to help women attain equality. She was clearly prepared and poised to address these issues at the panel on Tuesday. But the moderator insisted on putting her through her paces first.

“The German audience is not that familiar with the concept of a First Daughter,” she said in introducing the American guest. “What is your role? Who are your representing? Your father, as the President of the United States? The American people? Or your business?”

Trump countered with a broad if nervous smile: “Certainly not the latter,” she said. The rest of her response was a practiced show of humility, highlighting her eagerness to learn as she adjusts to a White House position that is, as she put it, “rather unfamiliar.”

This might serve as a lesson for Ivanka. As she continues adjusting in the coming months to her new role in world affairs, the First Daughter should expect to be quizzed on her policy credentials. And, in the process, she’ll have to be ready to answer for some of the awful things that her father has said in the past.

It’s a moment of caution for Merkel as well. Her attempts to forge a working relationship the White House is not likely to earn much applause from her own electorate, which was appalled by some of the statements that came out of the Trump campaign last year. Showing too much affection for the new U.S. Administration may even risk her own standing in the polls ahead of elections due this fall.

But pleasing all sides may not be possible for Merkel. An avid viewer of cable news, Trump is sure to catch the blanket coverage of Ivanka’s appearance on Tuesday, and he won’t be thrilled by the public humiliation of his daughter. For all that Merkel knows of the hotheaded President, he may even be inclined to blame Ivanka’s host.

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