Ric Grenell was confirmed today as the Trump administration's ambassador to Germany, despite a history of offensive tweets and comments.

The Senate voted to confirm the 50-year-old Grenell 56-42, mostly along party lines. Both of the senators from Grenell’s home state of California, Sen. Kamala Harris and Dianne Feinstein, opposed his confirmation.

The longest serving U.S. spokesman at the United Nations, he previously served four U.S. ambassadors to the U.N. and was rumored to be Trump’s pick for U.N. ambassador himself, a job that ultimately went to Nikki Haley. While he’s supported LGBT rights—including signing a 2013 amicus brief to the Supreme Court in support of marriage equality—there was serious concern about his attitude toward women. In a 2011 tweet, Grenell claimed Rachel Maddow “needs to take a breath and put on a necklace.”

In other tweets, he wondered if out lesbian Callista Gingrich “snaps on” her hair and suggested Hillary Clinton “is starting to look like Madeleine Albright.”

The 50-year-old diplomat also allegedly once told a female staffer, “‘Didn’t your mother ever tell you only whores and very small children wear red shoes?’” according to a 1995 Washington Post profile.

“Anybody who knows me knows that I am a very caring person and very sensitive—and I also appreciate good humor,” Grenell explained to Sen. Chris Murphy (D-CT). “Unfortunately, there are times where what was intended to be humorous turned out to be not so humorous, and, again, that was never my intention and I regret that.”

Those comments are particularly problematic considering Grenell is our liaison to a nation led by the most powerful woman in the world, Chancellor Angela Merkel.

His appointment comes 16 months after Trump took office and seven months after his name was first submitted. Grenell cleared the Senate Foreign Relations Committee in September by a 11-10 vote, also along party lines. He is the first openly gay appointee in the Trump administration, and the eighth openly gay diplomat in U.S. history.

Though, despite assertions by Fox News and the Log Cabin Republicans, he is not the first openly gay ambassador appointed by a Republican president: That honor goes to Michael Guest, confirmed as the U.S. ambassador to Romania in 2001.

“Log Cabin Republicans will not forget the votes of the Democratic senators who stood in opposition to Grenell’s confirmation, nor the roaring silence from LGBT advocacy organizations who did nothing to achieve this tremendous milestone in LGBT history,” declared Log Cabin Republican head Gregory T. Angelo.