Michelle Obama Reveals Her Dating Red Flags and What She Misses Most About the White House
Relationships December 19, 2024
Former First Lady Michelle Obama appeared on Tuesday’s episode of “The Jennifer Hudson Show,” and based on her casual chat with Jennifer Hudson, you’d never know it was her first time visiting the Happy Place!
“I am so proud of you,” Michelle told Jennifer after walking onstage to thunderous applause from the studio audience. “I feel like you’re mine.”
“I feel like I’m sitting here with family,” Jennifer responded.
“We are family — South Side!” said Michelle, who also hails from JHud’s hometown of Chicago.
Check out the best moments from these Chicago sisters’ intimate sit-down!
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Michelle shared with Jennifer how she hopes her latest book, “Overcoming: A Workbook” — a companion to her New York Times bestseller “The Light We Carry” — can help people overcome fear in their lives.
“This workbook gives you some guides, some real practical practices, steps, things to think about to find your own tools,” she told Jennifer. “A lot of my tools come from helping me think about what I’m really afraid of, and is that fear really worth holding me back?”
She continued, “Think about times that you were afraid in life, and what is the fear about? Is it a real danger, something you need to be afraid of? Or is it some story that you’ve told yourself about?”
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View Story“I want people to be encouraged to push beyond their fear and to get comfortably afraid,” said Michelle. “A little fear keeps you moving forward.”
For example, the former first lady revealed that she was terrified when Barack first talked to her about running for president. She initially shot it down because she feared “change, and the unknown, and my girls, who were 7 and 10 at the time, not wanting to uproot them.”
She ultimately decided to challenge her fear instead of succumbing to it. “We can get through this; we’ve done hard things before,” she recalled thinking. “I don’t want to tell [Sasha and Malia that] we didn’t do this thing because Mom was afraid of change. I want to look them in the eye and say, ‘We did something really hard together, and we made it through.”
How Her Book Honors Her Late Mother
Jennifer has sung for the Obamas many times, but one performance that was truly significant to Michelle was when the EGOT recipient sang “Amazing Grace” at the funeral for her mother, who passed away in May 2024.
“She sang so hard that she left the stage and was still singing,” remembered Michelle. “You brought us to our knees.”
“The beauty of this book was that I was able to write a love letter to my mom,” said an emotional Michelle. She explained that “Overcoming: A Workbook” was inspired by “the common sense wisdom she left me with, like ‘Your voice matters, I see you, you got power.’”
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View StoryRevealing Her Dating Red Flags
Michelle discussed why she decided to executive produce the Netflix reality series “The Later Daters,” which chronicles the dating lives of senior women.
“I always wanted to do a quality show about aspirational folks of our age, because this is what 50 and 60 and 70 looks like nowadays,” said Michelle.
Joined by dating expert Logan Ury and show participant Dr. Anise Mastin on the couch, the ladies shared their dating red flags.
Liking another woman’s social media posts? “I don’t like that!” said Michelle, shaking her head. Same for bringing up an ex on a date.
But talking politics on the first date? Logan and Anise say no way, but the former first lady — not surprisingly! — is enthusiastic about talking politics! “That’s not a red flag. I want to know!” she said. “Let me not waste any time.”
Why It’s So Hard to Shop for Barack
Though their Christmas vacation spot is always a given — the Obamas spend their holiday in Barack’s home state of Hawaii every year — it’s getting a gift for her husband that often leaves Michelle scratching her head.
“He’s really hard to shop for,” Michelle said of the former president. “He golfs, and there’s only so many golf balls you could get a dude.”
According to Michelle, Barack doesn’t want anything except “a nice letter. And he means it!”
Jennifer asked who the best gift-giver in the family is, and Michelle kept it 100: “I think I am, because I’m really paying attention to everyone,” she said. “I’m the one who makes Christmas happen.”
The Way She Surprised an Inspiring Teacher
Tanisha Milton, voted Educator of the Year for Boston Public Schools, got the surprise of a lifetime when Michelle shocked her with a surprise appearance!
Tanisha, a teacher at a Title 1 school, grew up in the same neighborhood as her students and knows firsthand the challenges they face outside the classroom. She recently piloted an AP African American history course at her school, and her students achieved the highest test scores in the country.
“The passion with what you speak about what you do and your kids and your truth — we need people like you,” Michelle told a teary-eyed Tanisha.
“We do not do enough to lift up educators like you,” the former first lady added. “You are changing lives. It takes one kid to be seen by you, and you change their lives.”
What She Misses Most About Living in the White House
It’s been eight years since the Obamas moved out of the White House at the end of Barack’s second term. As for what she misses most about living in “The People’s House” — it’s the people!
“I always say the staff,” she said. “The folks who serve the families through every administration. They did it with dedication, they took care of my girls, they made sure they weren’t spoiled, they loved my mother.”
“I miss every single person, from the folks who worked on the grounds to the head usher,” she continued, adding, “That was home for us.”
Michelle, you always have a home here at the Happy Place, too!
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