10 Lessons From My Last Love (That Made All The Heartache Worth It)

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what heartbreak can teach you
Love, Self

And what heartbreak can teach you.

Ben was one of the best conversationalists I’d ever met. He was also an incredible storyteller and an even better listener. And he could make me laugh like nobody else.

We met at a grocery store. Technically, we first connected on a dating app, but hours before our initial date, Ben and I literally bumped into each other at the Whole Foods in our neighborhood. He was there buying deodorant for our date.

I had just finished dance class and was running in for a water. He spotted me from across the store and moments later we were chatting. As we parted ways to get ready for the evening, I got a text from him saying, “You’re just as beautiful as your photos.”

The conversation and the chemistry flowed effortlessly between us. He had this mix of honesty and openness coupled with confidence that’s sexy and rare. He was always telling me about something interesting he’d just read or would respond to a question in a way that pushed my thinking.

One evening, after we’d spent the day on a boat together, I asked him what he loved so much about being on the water. He told me about how in Catch-22, one of the main characters does things that are boring as a way to prolong life by seemingly slowing time.

“There’s a luxurious feeling to spending a day on a boat with nothing to do,” Ben replied. I loved his thoughtful explanations, his unexpected answers, and the creative, quirky way that he viewed the world.

We continued to see each other for two months and had amazing adventures — from him teaching me how to golf to day trips to the sand dunes, a salmon cook-off and homemade tortilla and ceviche-making, badminton on the beach, movies in the park, leisurely bike rides, romantic boat rides, lazy brunches, strolls through Chicago neighborhoods, ping pong, and parties with friends. There was also incredible romance, affection, and chemistry.

About a month into our dating, I learned that Ben was just out of a two-year relationship and "not looking for anything serious.” I asked him if he needed time, space, or both. “Time," Ben said.

My ego was a little bruised but I figured I’d continue to date other guys and move him down a peg on my priority list. The truth was, though, none of the guys I was seeing even came close to Ben.

Our last date together started with a romantic walk, then cocktails and delicious conversation overlooking the city, and sparks in the bedroom. Nothing unusual or out of the ordinary happened that night, but I never heard from Ben again.

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I had forgotten how much it hurt — missing his touch, the way his texts put the biggest smile on my face, the tantalizing anticipation of our time together, knowing how much I turned him on, and the intoxicating feeling of being turned on, too. In that moment and in the days that followed, I felt this horrible mix of embarrassment, sadness, and loss.

It’s easy to blame yourself and beat yourself up when someone you’re dating rejects you, especially when it happens without a conversation or closure.

The thing that kept me going is that I believe our relationships are our greatest teachers. They teach us about others and, most importantly, they teach us about ourselves — our strengths, our blind spots, and the areas that we can grow.

While I still miss Ben quite a bit, more than anything I’m grateful for the motivation this experience gave me to reflect, grow, binge-listen to Beyoncé and become a wiser, stronger version of myself. Below are the top 10 lessons I learned about what heartbreak can teach you that made all this pain worth it.

1. A person's incredible qualities and the attraction you feel is never reason enough to continue dating someone.

Most important is how they treat you and that they choose you. The minimum bar we should all have for someone we date is that they want to date us too. If that's not the case, move on and invest your time in meeting a man who does. It can be really hard to honor this when you feel truly seen by someone.

With Ben, I let my guard down, was fully myself, and shared fantasies and parts of myself that I hadn't with anyone else. I got attached to that incredible feeling of raw honesty and conflated it with my feelings for Ben. Yet, if someone is truly interested, they pursue you, plan dates, and progress the relationship, they don't disappear.

2. Let people into your life gradually.

It can be so tempting, especially when it's been a long time since you've had intense feelings for someone, to open your life up fully to them. We want them to meet the people we're close with, we want to learn what makes them laugh, how they love to spend their time, what they want to experience in life, and we want to spend a lot of time with them, often naked.

Yet, our time is the most precious thing we have. No matter how much we think we like someone, at every step of dating the other person needs to earn our time along with our trust. 

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3. When dating, scarcity leads to settling.

The best thing you can do in the early stages of dating, even when you're developing strong feelings for someone else, is to continue to date lots of people. Abundance and options always help you to uphold your standards. 

4. You'll never be good enough for a person who isn't ready or right for you.

Don't waste your time trying to figure out why someone isn't interested. Don't spend your energy trying to convince someone of your value. Ignore what you can't control because so much of who we are gets filtered through the lens of someone's past and their current blueprint.

Focus on the parts of yourself you can improve and spend your time and energy meeting new people and bringing your best to the people who matter.

5. Self-awareness is knowing what you need in a relationship.

Self-respect is valuing yourself enough to communicate what you need and not settling for anything less. People value us only as much as we value ourselves.

Ben communicated that he wasn't interested in being in a serious relationship. Honoring my standards would have meant breaking things off right then rather than hoping he'd change his mind. Never compromise your standards just because you like someone in order to make something that's not working, work.

6. During the first few dates, it's easy to just enjoy the moment and someone's company.

After several amazing dates, it's natural for women to think about what's next because our greatest need is to feel safe, and being in a defined relationship provides that. Men, on the other hand, crave freedom, the opposite of safety, which puts our needs in direct conflict.

The solution is to go into experiences without expectations. Enjoy them for what they are, not for their potential.

7. Consider: Would I regret spending this time together, expressing this emotion, or investing at this level if things were to end tomorrow?

If the answer is yes, as it was for me in moments with Ben, you're probably moving too fast and making someone a priority who hasn't earned that role yet in your life.

8. You never need someone to give you closure.

No contact is closure. Disinterest is closure. Closure comes from within. Even though Ben disappeared, I gave myself the closure I needed from knowing my standards and no longer letting him be an option in my mind because he wasn't meeting mine for communication or investment.    

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9. No dating experience is ever a waste of time.

Even relationships that don't work can be amazing teachers and spark gratitude. One of the things I'm most grateful for about my time with Ben is he illuminated new characteristics that I'm looking for in a partner and qualities that I want to develop in myself.

Ben had very eclectic interests — offbeat authors, experiential art museums, gong meditation, glamping, and golf. His creativity and the passionate way he shared his interests with me were unexpected turn-ons and things I can now look for in another partner. He was also a killer listener, brought amazing energy to our interactions, and was an expert problem solver.

My attraction to these qualities showed me that they're all characteristics that I want to cultivate more of in myself.

10. Responding to a breakup by reflecting, learning, and growing is always the answer.

When Ben disappeared, I got my hands on as many podcasts, books, and articles on relationships, dating, and attraction as I could. The work I invested will make me a better partner in my next relationship. His actions inspired me to become a stronger version of myself and elevate my standards for myself and the men I date.

I can't think of a greater gift you can give someone than the inspiration to evolve. I believe our relationships are our greatest teachers. They inspire us to examine our pasts and face the stories we live that dictate what we believe is possible for ourselves. They teach us about others and, most importantly, they teach us about ourselves — our strengths, our blind spots, the areas that we can grow, and the standards that we have for ourselves. 

Sometimes it takes a heartache to realize you're worth more than you were settling for. And when you know how much you're worth, you never give people discounts. 


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Leah Marshall leads strategic partnerships and new business development for a Chicago-based marketing company. Leah draws much of her inspiration from her favorite podcasts: The School of Greatness, Impact Theory, and The Model Health Show. You can connect with Leah on Twitter at @LeapCast.