What I Wish I Knew About Falling In Love Again After Heartbreak

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“Maybe this one doesn’t kill you, Molly,” a friend said to me over FaceTime.

I was telling her about my new relationship and my resistance to going “all the way in” with him.

I had left New York City when rumors of a shutdown began to spread. I thought I would be gone for a couple of weeks.

Weeks turned into a month, which turned into two months that turned into my boyfriend saying “you’re not coming back, are you?” My heart hurt hearing him say that, having left him behind. Especially after having such an intimate goodbye and three days together leading up to my departure. An intense internal battle.

What do I do?

What did we owe each other?

“I want you to come back.”

“I want you to come here.”

Somehow despite everything going on, our relationship lasted through the most trying months of the pandemic. He showed up, I showed up.

For a while, it seemed like we would really make it through this.

We were both clinging to the last time we saw each other, hopeful we could have it back.

Then, it happened.

I felt that feeling. I imagined telling people how we spent the “honeymoon” phase of our relationship over Zoom meditating together and watching Governor Cuomo’s daily press releases from many miles apart.

Opening our hearts to each other as the world stood still and what it would be like to see each other again, what we would do. That first reuniting embrace.

“When things are ‘normal’ again” was a daily mutterance.

But our patience was starting to wear thin.

We got in a fight about an Instagram post. Our first actual fight. Deep down we both knew it wasn’t about the post, though. It was about two people that had both been hurt by love and who were now falling in love in what felt like an impossible world to navigate.

Nothing at all felt certain and we both knew what this ride would entail. Did we want to open that window? Take ourselves through what happened next…

We got on the phone to process the fight but I didn’t “give it up” to him.

What I couldn’t bring myself to say was, “I’m falling in love with you, I feel crazy, and I’m absolutely terrified.”

He was an intuitive being and knew what was going on but he couldn’t say it either. There was a ton of irritation and frustration now between us that we couldn’t skillfully navigate through. We ended the call anyway.

Twenty minutes later he popped back up on my phone, calling again.

“Molly, is there something you’re not telling me?”

I was standing in my mom’s kitchen and I knew this was the choice point. Where I either leaned in and surrendered to the ride we were both about to take or, close the window. Once the window gets closed, it doesn’t always open back up in the same form.

Sometimes there are second chances you just don’t get.

“No,” I tell him.

“There’s nothing else I need to say.”


A week later another call.

“Molly, I’m about to lose my Visa.”

“What does that mean?”

The words of someone on the other side of a closed window.

We were officially off the merry-go-round.

Here are some things I wish I knew about starting to fall in love after a previously painful heartbreak.


You may still think about your ex

Maybe it was naivety or delusion but I assumed that after enough time passed, enough therapy, coaching, “healing,” the memories and feelings of my last painful breakup would pass.

I learned it’s actually the opposite. When you begin to date again, open your heart and have new experiences with someone new, the same set of neural pathways that were active in a previous relationship get opened back up leaving you susceptible to thinking of past love and past partners.

Apparently, 60% of us experience thinking about an ex during sex in a new relationship. It could be because you simply haven’t created a sexual narrative with your new partner and need more time, explains Elizabeth Earnshaw MFT.

Know that it’s normal to still periodically think of an ex, that it may be happening to reveal parts of the past that haven’t fully been healed. It doesn’t mean you need to end a new relationship but getting support and leaning in with curiosity, versus avoiding, is your best bet.


You may be more protective of your heart

What goes up . . . must come down. The amount of joy, love, and depth I experienced in my last relationship was also followed by an immense amount of pain, grief, and sadness when it ended.

This time around when I felt that window opening with a new boyfriend, I was no longer blissfully ignorant. I knew very well what the ride of “love” entailed. I knew that once the spot opened, we’d have to see it all the way through.

My heart got a lot more care and attention. I wasn’t willing to be quite so reckless and impulsive. I ultimately chose the “maybe we sit this one out” route when the prospect of dating someone on the verge of deportation was a real reality.

Discernment is okay and expected.


You may need to rewire your beliefs about love

Even though I do this for a living (relationship coaching) that doesn’t always mean I’m an expert in seeing my own patterns in my own life.

When my friend said “Molly, the last one took you down so maybe this one takes you up. You know there’s a lot of joy . . . and fun to be experienced in this whole love thing, right?”

It was still hard to imagine love being anything but pain and hardship even though I logically knew differently.

I wish I had been more prepared and had been able to communicate through my experience so that I hadn’t subtly pushed him away in this re-opening process.

Give yourself time and grace. You are learning to reuse a muscle that may have atrophied and experienced a real injury.


You may have a lot of pride

It’s hard not to relate to a breakup as a “failure.”

When my old relationship ended I knew I had a lot of inner work to do to find my parts of responsibility.

When I did finally feel ready to date again, I felt confident I could make a new connection work. In my mind, I had “done everything right” this time.

Ultimately, in my reflection now, that newfound sense of pride was really just protecting me from a lot of the unprocessed shame I felt about the last relationship ending.

It was a false sense of power talking, “I won’t mess up a good relationship again.”

Pride is quite a deadly sin. It can derail you very quickly.

My last relationship ending was a gift. He wasn’t the partner for me. There were lessons and huge experiences of transformation that would not have been available had we stayed together. From where I stand now, there was no reason to be ashamed.

What if we actually celebrated transitioning out of a relationship as much as we celebrated transitioning into them? Celebrating that breakups signify new boundaries, vulnerability, honoring each other’s needs, and acknowledging when something feels “complete” or “done.”

What if we let those we love hold us through our grief and fear without pushing anyway one. Acknowledging the bravery it takes to say goodbye with love and respect is how desire & intimacy coach Aimee Batuski explains a new possibility of how we relate to breakups could look.


The reality is that with everything great there will also be risks. Yes, love may be painful but it also has the potential to be amazing, joyous, and life-changing. It’s important to consider the whole, wide spectrum.

With pain, through its contrast, we develop a greater range of sensation giving us depth and wisdom. Ultimately, I invite you to not fear an ending or a beginning because we never really “lose” love. It just changes form.


Want to know what’s really keeping you from finding love? In my 60 min masterclass How to Find Your Partner in Crime, I’ll walk you through the pitfalls that keep women just like you from experiencing lasting love. AND I’ll show you how to shift your perspective so you can stop repeating sabotaging patterns. Claim your spot HERE to join me live.

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