#howimend: OKREAL Founder Amy Woodside Shares Her Post-Breakup Rituals


By Kate Paguinto

Hailing from New Zealand and based in New York City, Amy Woodside is the founder of OKREAL: a platform and community for women who want to live fulfilled and meaningful lives. In addition to their beloved interviews, OKREAL hosts panels, workshops and mentor circles with the mission of uplifting and furthering the development of women through stories of leadership, confidence and purpose. 

We asked Amy about her experience with heartbreak and she shared how letting go of anger and animosity towards her exes helped her stay #onthemend. 


If you think back to the first time you were heartbroken, what advice would you give to that younger version of yourself?

"My heartbreak has always (fortunately?) been a result of me breaking up with someone else, starting with my high school boyfriend. So to my 15-year-old self I would say: You won't regret breaking up with him. Stop wasting time over someone who isn't right for you. Stop being a drama queen. There are a lot of men who are going to want you, be good for you, make you laugh and treat you well. Or in Cheryl Strayed's words: Be brave enough to break your own heart."

What has heartbreak taught you about yourself?

"That it is always about my own self worth and never about the other person."

What are your rituals during a breakup? What things/practices/people helped you mend?

"Usually a vicious cycle of over analyzing, crying, other boys—until I realize my time and energy is worth more than that. I think you have to exhaust the shitty choices after a breakup to get to the ones that actually help you heal."

Thinking back to breakups you’ve had, did you have any breakup vices (checking your ex’s Insta, etc) and how do you conquer them?

"I've always had pretty messy breakups, was never that good at cutting things clean. I've found that leaving the country is a great solution!"

What’s the biggest lesson you’ve learned about love so far in your life?

"That everything comes down to what you're willing to accept, and what you're willing to accept has everything to do with how much you love and value yourself."

Do you think exes can be friends? Do you stay friends with your exes on social media?

"Perhaps this is a privileged answer, but in my case, yes. I don't hold any grudges against any exes, they've all taught me something. Some I hold in higher regard than others, but I still don't feel any anger towards the guys who didn't treat me that well. We all hurt and disrespect other people who don't deserve it, myself included. Holding on to animosity towards others impacts you, not the other person. And, I have better things to worry about than some dude who was mean to me 10 years ago."


What keeps your heart open, despite the heartbreaks you’ve had in your life?

"Is there another option? I think we all need that time of mourning, self compassion, and patience in finding our feet again, but after that phase we have to make a choice. You can choose to be miserable and bitter, or you can choose to pick yourself up. I’ve found the latter leads to much better things."

What is your favorite song about heartbreak?

"Bic Runga, Sway (Kiwi 90s singer, on heavy rotation in the early 2000’s) and The Carpenters, Ticket To Ride (Or anything by The Carpenters really)"

What is your favorite movie about heartbreak?

"Stepmom. Sob every time."

What projects are you currently working on, and looking forward to most?

"Expanding OKREAL mentor circles! These are curated groups of women who meet to support each other in reaching their goals. After launching these 6 months ago, our waiting list has grown into the hundreds and we will soon be announcing our program expansion which will help us accommodate our incredible community. You can learn more about OKREAL circles here."

writer photo

Kate Paguinto

Kate is a Content Strategist at Mend and co-owner of a small business called Dizzy Cactus. She likes puns, Wes Anderson, and the Oxford comma.

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