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Top 15 Kerry Winfrey Quotes (2025 Update)

Kerry Winfrey Quote: “Sometimes we get chances – opportunities – that we’re meant to take. And if you take the leap, things will open up and change. And if you take a step back instead? Okay. That’s your decision. But you’ll never know what you were supposed to find out.”

1. “Sometimes we get chances – opportunities – that we’re meant to take. And if you take the leap, things will open up and change. And if you take a step back instead? Okay. That’s your decision. But you’ll never know what you were supposed to find out.”

— Kerry Winfrey

Kerry Winfrey Quote: “The things that suck still suck, but they’re allowed to be happy. And maybe it means so much more that they’re happy, knowing that they still carry that sadness with them.”

2. “The things that suck still suck, but they’re allowed to be happy. And maybe it means so much more that they’re happy, knowing that they still carry that sadness with them.”

— Kerry Winfrey

Kerry Winfrey Quote: “He used three exclamation points? That kind of irresponsible punctuation must mean something’s up.”

3. “He used three exclamation points? That kind of irresponsible punctuation must mean something’s up.”

— Kerry Winfrey

Kerry Winfrey Quote: “Maybe my person and I won’t fit together like two halves of the same whole, but neither did Tom Hanks and Meg Ryan in You’ve Got Mail or Sleepless in Seattle. They didn’t erase each other’s pain; they just made it bearable.”

4. “Maybe my person and I won’t fit together like two halves of the same whole, but neither did Tom Hanks and Meg Ryan in You’ve Got Mail or Sleepless in Seattle. They didn’t erase each other’s pain; they just made it bearable.”

— Kerry Winfrey

Kerry Winfrey Quote: “I guess if we’re talking about my anxiety, the even truthier truth is it started way before that.”

5. “I guess if we’re talking about my anxiety, the even truthier truth is it started way before that.”

— Kerry Winfrey

Kerry Winfrey Quote: “Everyone thinks of romantic comedies as being these sappy, unrealistic stories where love conquers all and everyone ends up happy at the end. But that’s not what her movies were at all. Like, in Sleepless in Seattle, you can’t really get any sadder that Tom Hanks missing his dead wife. And in You’ve Got Mail, Meg Ryan misses her mom and loses her store. None of that gets resolved by the end. It’s not like Tom’s wife comes back to life, and Meg Ryan still loses the business her mom built.”

6. “Everyone thinks of romantic comedies as being these sappy, unrealistic stories where love conquers all and everyone ends up happy at the end. But that’s not what her movies were at all. Like, in Sleepless in Seattle, you can’t really get any sadder that Tom Hanks missing his dead wife. And in You’ve Got Mail, Meg Ryan misses her mom and loses her store. None of that gets resolved by the end. It’s not like Tom’s wife comes back to life, and Meg Ryan still loses the business her mom built.”

— Kerry Winfrey

Kerry Winfrey Quote: “After tomorrow, I’ll see a different face staring back at me from the mirror – at first, a swollen face, but then one with a smaller jaw and a straighter smile. This is what I’ve wanted for years, but standing on the edge of all this change, I feel like I want to pause time and remember exactly what if feels like to be here now – in the before.”

7. “After tomorrow, I’ll see a different face staring back at me from the mirror – at first, a swollen face, but then one with a smaller jaw and a straighter smile. This is what I’ve wanted for years, but standing on the edge of all this change, I feel like I want to pause time and remember exactly what if feels like to be here now – in the before.”

— Kerry Winfrey

Kerry Winfrey Quote: “This isn’t a sob story, sweetie. That’s just what life is. Even if you’re happy with the path you went down, part of you always wonders what was on that other road you passed a few miles back. That doesn’t mean it’s some grand tragedy. But it’s a loss all the same.”

8. “This isn’t a sob story, sweetie. That’s just what life is. Even if you’re happy with the path you went down, part of you always wonders what was on that other road you passed a few miles back. That doesn’t mean it’s some grand tragedy. But it’s a loss all the same.”

— Kerry Winfrey

Kerry Winfrey Quote: “The air is slightly chilly, but there’s a promise in the air. It might be rainy and cold and, okay, it wouldn’t be unheard of if it started snowing in April, but warm weather is coming. Things are growing, and I can feel it.”

9. “The air is slightly chilly, but there’s a promise in the air. It might be rainy and cold and, okay, it wouldn’t be unheard of if it started snowing in April, but warm weather is coming. Things are growing, and I can feel it.”

— Kerry Winfrey

Kerry Winfrey Quote: “I know your work matters. No one’s suggesting that it doesn’t. But the people who love you matter, too. And if you keep blowing everyone off to give one hundred percent of yourself to work, someday you’re gonna wake up and no one will be there anymore.”

10. “I know your work matters. No one’s suggesting that it doesn’t. But the people who love you matter, too. And if you keep blowing everyone off to give one hundred percent of yourself to work, someday you’re gonna wake up and no one will be there anymore.”

— Kerry Winfrey

Kerry Winfrey Quote: “But what if I stop giving everyone everything, and then they don’t give me anything back to fill the void?”

11. “But what if I stop giving everyone everything, and then they don’t give me anything back to fill the void?”

— Kerry Winfrey

Kerry Winfrey Quote: “Sure, it’s absolutely ridiculous to turn down a real-life guy because of a movie star, like saving myself for one of the Jonas Brothers in junior high, but it’s how I feel.”

12. “Sure, it’s absolutely ridiculous to turn down a real-life guy because of a movie star, like saving myself for one of the Jonas Brothers in junior high, but it’s how I feel.”

— Kerry Winfrey

Kerry Winfrey Quote: “That’s the tone of voice you use when you’re about to give unsolicited advice.” “That’s the only kind I can give you. You never solicit my advice, even though it’s impeccable.”

13. “That’s the tone of voice you use when you’re about to give unsolicited advice.” “That’s the only kind I can give you. You never solicit my advice, even though it’s impeccable.”

— Kerry Winfrey

Kerry Winfrey Quote: “Shush. Let the man emote. We need to encourage straight men to share their feelings; that would solve, like, ninety percent of the world’s problems.”

14. “Shush. Let the man emote. We need to encourage straight men to share their feelings; that would solve, like, ninety percent of the world’s problems.”

— Kerry Winfrey

Kerry Winfrey Quote: “I try not to judge people who face situations I’ve never faced.”

15. “I try not to judge people who face situations I’ve never faced.”

— Kerry Winfrey

Kerry Winfrey Quote: “No one in the history of ever has called me chill. I came out of the womb and the doctor was like, ‘Whoa, get this newborn into a baby yoga class, she’s stressed.”

16. “No one in the history of ever has called me chill. I came out of the womb and the doctor was like, ‘Whoa, get this newborn into a baby yoga class, she’s stressed.”

— Kerry Winfrey

Kerry Winfrey Quote: “I just don’t want you to live your whole life being afraid of change when you’re already a star.”

17. “I just don’t want you to live your whole life being afraid of change when you’re already a star.”

— Kerry Winfrey

Kerry Winfrey Quote: “Sometimes it helps to think back to what made us happy when we were young, before we met people who told us our dreams were silly or unrealistic. What lit up your heart when you were a kid? Maybe that’s your thing.”

18. “Sometimes it helps to think back to what made us happy when we were young, before we met people who told us our dreams were silly or unrealistic. What lit up your heart when you were a kid? Maybe that’s your thing.”

— Kerry Winfrey

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