Former vice president Joe Biden regularly touts his support for minority groups while campaigning for the presidency. He believes his record advocating for their equality speaks for itself and is unmatched among his opponents.

When Sen. Kamala D. Harris (D-Calif.) put Biden on the defensive in last week’s debates over his position in the 1970s on school busing, Biden reiterated his commitment to civil rights issues. He told Harris, a prosecutor: ”If we want to have this campaign litigated on who supports civil rights and whether I did or not, I’m happy to do that. I was a public defender. . . . Everything I have done in my career, I ran because of civil rights, I continue to think we have to make fundamental changes in civil rights, and those civil rights, by the way, include not just only African Americans, but the LGBT community.”

But the way Biden goes about connecting with these groups, or giving his analysis of other Americans’ fears about them, is often awkward, and can even suggest that he does not grasp the challenges of their experiences as much as he thinks he does.

Here are a few examples of where those attempts have made for head-scratching sound bites that diluted his attempts to find common cause.

1. Praising segregationists

At a June fundraiser in New York, Biden spoke about the importance of “bringing people together” while discussing his ability to work well with late senators James Eastland (Miss.) and Herman Talmadge (Ga.), two Democrats who were staunchly opposed to civil rights and racial integration.

While reflecting on his relationship with Talmadge, Biden said: “Guess what? At least there was some civility. We got things done. We didn’t agree on much of anything. We got things done. We got it finished. But today, you look at the other side and you’re the enemy. Not the opposition, the enemy. We don’t talk to each other anymore.”

Biden included an anecdote about his closeness with Eastland that is drawing particular scrutiny from his Democratic opponents and other critics. “He never called me ‘boy.' He always called me ‘son,' " Biden said of the Mississippian.

The backlash was broad.

“What does Biden think Black voters hear when they listen to him talk about his buddy the segregationist being not that bad of a dude?” Zerlina Maxwell, a former Hillary Clinton campaign official, asked on Twitter.

And Adrianne Shropshire, executive director of Black PAC, a group focused on increasing black voter turnout, previously told the Fix:

“All the most recent polls, including our own, show that VP Biden is leading among African American voters of all ages. But his most recent comments draw attention to a set of issue concerns that black voters have not yet measured him against. Black voters in our most recent poll identified racism and discrimination as one of their top issue concerns so how the vice president characterizes his previous relationship with his racist colleagues, matters.”

2. “Hoodies” and “gangbangers”

While discussing the need for criminal justice reform at a luncheon on Friday for Rainbow PUSH, a civil rights organization founded by Jesse L. Jackson, Biden spoke of the need for people to not make judgments about kids based on their appearance. He said:

"We’ve got to recognize that the kid wearing a hoodie may very well be the next poet laureate and not a gangbanger.”

The comment evoked the death of Trayvon Martin, a black teen killed in 2012 while wearing a hooded sweatshirt by a security guard who said he was intimidated by his appearance. But Biden’s example also played into stereotypes about black youths’ appearances that some listeners found uncomfortable.

Gay rights activist Charlotte Clymer tweeted:

“I was at a place with TVs for lunch when Biden said ‘a kid in a hoodie may be the next poet laureate and not a gang banger’ and several folks in the room watching, myself included, simultaneously went ‘Oh no...’”

And Baylor Johnson, a spokesman for ACLU of Texas noted:

"There is ... so much to unpack in Biden’s ‘hoodie/gangbanger/poet laureate,’ but I’m going to focus on ‘poet laureate,’ because the implicit awe at a black man being recognized for writing poetry is basically a more specific version of ‘he’s so articulate.’”

3. The “cleanliness” of Barack Obama

Biden often points to his time working with President Barack Obama as proof of his commitment to diversity, but while reflecting on his former opponent during his 2008 presidential run, Biden praised Obama while playing into stereotypes about black people’s appearances and intelligence. He also seemed to inadvertently dismiss all of the black lawmakers with whom he has worked.

In a New York Observer article, Biden is quoted as saying:

“I mean, you got the first mainstream African American who is articulate and bright and clean and a nice-looking guy. I mean, that’s a storybook, man.”

Jackson, a black man who ran for president against Biden in 1988, told CNN at the time:

“Knowing Joe Biden the way I do, I’m sure he didn’t mean it as off-color, but it is certainly highly suggestive."

4. The “gay waiter” anecdote

At a fundraiser in Seattle during the city’s pride celebrations, Biden sought to praise the community for its advancement on gay rights.

According to pool reports, Biden said if someone at a business meeting in Seattle "made fun of a gay waiter" five years ago, people would have just let it go.

Groans were heard in the crowd while someone yelled “Not in Seattle,” in defense of the city’s reputation as an accepting place for LGBT people.

Others expressed frustration at Biden appealing to gay stereotypes by mimicking a gay waiter speaking with a lisp and an effeminate voice.

Aisha Moodie-Mills, a political strategist who is gay, pushed back on Biden’s lack of awareness of Seattle’s support for the gay community. She tweeted:

“Seattle had a GAY MAYOR 5 years ago and now has a LESBIAN MAYOR in office. @Joe Biden fumbles again. Folksy is becoming foolhardy. Think he needs a time out to regroup. Biden’s ‘gay waiter’ comment on LGBTQ rights falls flat in Seattle”

4. Indian immigrants and convenience stores

While attempting to connect with an Indian American supporter in 2006, the former Delaware lawmaker spoke of the growth in his state’s Indian American population.

“In Delaware, the largest growth of population is Indian Americans, moving from India. You cannot go to a 7-Eleven or a Dunkin’ Donuts unless you have a slight Indian accent. I’m not joking,” he said.

The association of Indian Americans with convenience stores is a stereotype members of the group have spoken out against, saying it has harmed many Americans’ views of the community.

In the “The Problem With Apu” documentary, Indian American comedian Hari Kondabolu said that Apu, a character on the sitcom “The Simpsons” who works at Kwik-E-Mart convenience store, is a racist stereotype — “a white guy doing an impression of a white guy making fun of my father.”

5. Joking about inappropriately touching women

After Biden was called out for touching women in ways that made some feel uncomfortable, he released a video promising he’d do better and suggesting that he understood how unacceptable his actions were in the #MeToo era.

But days later, he was joking with supporters about his new interactions with women.

My colleague Amber Phillips previously wrote for the Fix:

“While addressing union workers Friday, he made two jokes that seemed to belittle the women who accused him of touching them in uncomfortable and inappropriate ways.

Shortly after getting onstage Friday, Biden hugged International Brotherhood of Electrical Workers President Lonnie Stephenson, then said, ‘I just want you to know I had permission to hug Lonnie.’ The crowd laughed; Biden glowed.”

This was not the only time he joked about his new interactions with women, which left some with the impression that Biden doesn’t understand how hurtful his actions were as much as he claims.

6. “Entitled millennials”

In an effort to motivate young Americans frustrated with politics to get involved in the political process, Biden has played into the “entitled millennial” stereotype — the idea that young people are complainers with no desire to work hard.

“The younger generation now tells me how tough things are," he said at the 2018 Los Angeles Times Ideas Exchange. “Give me a break. No, no, I have no empathy for it. Give me a break. Because here’s the deal guys, we decided we were gonna change the world. And we did. We did.”

“And so, there’s an old expression my philosophy professor would always use from Plato, ‘The penalty people face for not being involved in politics is being governed by people worse than themselves,' ” he added. "It’s wide open. Go out and change it.”

While Biden has been in politics longer than anyone else on the left seeking the Oval Office, he risks his chances of getting the country’s highest position because he is competing with people who resonate with marginalized groups far better than he does.

If Biden is going to win the nomination, he will need the support of women, people of color and the gay community. But to win these groups, he will likely have to prove that he understands their challenges and, more importantly, that he takes their concerns seriously.