I almost didn’t say anything. That is the truth I don’t love admitting, but here it is. I was twenty-six, standing in a kitchen at a mutual friend’s birthday party, and I had already decided the man across the room was out of my league. He laughed loud, he made everyone in the room feel like the funniest person there, and I figured someone like that already had someone. I told myself I was tired anyway. I got my coat. I was halfway to the door when a friend grabbed my arm and said, “Just talk to him. What is the worst that happens?” So I turned around, walked back in, and said something dumb about the snack table. That man is my husband now, and we still laugh about how close I came to just going home.
I think about that hallway moment more than almost anything else in my life, because it could have gone the other way so easily. I could have gotten in my car and driven home and never known what I was missing. That is the thing about taking a chance on someone, it only works if you actually take it. Silence never got anybody a second date, and a maybe you never asked never turns into a yes. So today I rounded up thirty quotes about courage, risk, and telling someone how you feel, because sometimes we all need a little nudge to walk back through the door.
Bold Quotes About Taking the Chance
These are the quotes to read right before you hit send on that text or walk across the room.
- “You miss 100% of the shots you don’t take.” Wayne Gretzky
- “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” Michael Jordan
- “The most difficult thing is the decision to act, the rest is merely tenacity.” Amelia Earhart
- “Life is either a daring adventure or nothing at all.” Helen Keller
- “You only live once, but if you do it right, once is enough.” Mae West
- “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” Anaïs Nin
- “Faint heart never won fair lady.” English Proverb
Quotes About the Regret of Staying Silent
Nothing stings quite like wondering what could have happened if you had just opened your mouth, and these writers knew it.
- “‘Tis better to have loved and lost than never to have loved at all.” Alfred, Lord Tennyson, In Memoriam A.H.H.
- “I desire the things which will destroy me in the end.” Sylvia Plath, The Unabridged Journals of Sylvia Plath
- “Love makes your soul crawl out from its hiding place.” Zora Neale Hurston, Their Eyes Were Watching God
- “Above all, be the heroine of your life, not the victim.” Nora Ephron
- “The heart wants what it wants, or else it does not care.” Emily Dickinson
- “Who ever loved that loved not at first sight?” Christopher Marlowe, Hero and Leander
Wise Quotes About Courage in Love
These are less “go get ’em” and more the kind of steady wisdom that gets you through the shaky moment right before you speak up.
- “To love at all is to be vulnerable.” C.S. Lewis, The Four Loves
- “Success is not final, failure is not fatal: it is the courage to continue that counts.” Winston Churchill
- “Courage is not the absence of fear, but rather the judgment that something else is more important than fear.” Ambrose Redmoon
- “And, when you want something, all the universe conspires in helping you to achieve it.” Paulo Coelho, The Alchemist
- “When I dare to be powerful, to use my strength in the service of my vision, then it becomes less and less important whether I am afraid.” Audre Lorde, Sister Outsider
- “Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure.” Marianne Williamson, A Return to Love
- “You get in life what you have the courage to ask for.” Oprah Winfrey
- “Love recognizes no barriers. It jumps hurdles, leaps fences, penetrates walls to arrive at its destination, full of hope.” Maya Angelou
Fun and Modern Quotes to Hype You Up
And when you need something a little less poetic and a little more “get up and go do it,” these should do the trick. Sometimes a pop song lyric or a one-liner from someone who has clearly been there does more for your nerve than any old philosopher ever could.
- “What other people think of me is none of my business.” RuPaul
- “I don’t think you should wait. I think you should speak now.” Taylor Swift, Speak Now
- “You only live once: that’s the motto.” Drake, The Motto
- “The biggest risk is not taking any risk. In a world that is changing quickly, the only strategy that is guaranteed to fail is not taking risks.” Mark Zuckerberg
Here is what I know now that I didn’t know in that kitchen all those years ago. The fear never fully goes away, and it isn’t supposed to. You just decide the person, or the moment, or the version of your life you want, is worth walking back through the door for. So text him first. Tell her you like her. Ask him to coffee even though your hands are shaking. Write the letter, make the call, say the thing you have been rehearsing in the shower for weeks. The worst that happens is a no, and a no still leaves you exactly where you started, no worse off, just a little wiser. The best that happens might just be the rest of your life, a person you build a whole world with, a story you tell your friends for decades. Go shoot your shot. I am rooting for you, and honestly, so is everyone else who has ever stood in a kitchen wondering if they should just say something.
