Breaking Up is Hard to Do

Keri Lewis
6 min readAug 13, 2020
Image Credit: ID 121332524 © Pichai Pipatkuldilok | Dreamstime.com

The wild ride of online dating came to a halt on my date with the Lumberjack. Instead of rolling gently into the station, this ride ended with an unexpected bump into the barricade. A little dazed, I unlatched my safety harness and made my way on shaky legs to the exit, feeling a little high and a little scared. Thankfully, the Lumberjack was there to take my hand.

He’s not really a Lumberjack, by the way. He’s simply from Canada. When I told him I needed a nickname for him for my blog, he suggested Lumberjack, which suits him perfectly, as he is a sexy, rugged guy who loves the outdoors.

I am not, however, going to kiss and tell. The details of our first and second dates are a beautiful thing to be shared only by the two of us and the pages of my journal. If you are a friend or family member and you want to know more about the Lumberjack, make a pot of coffee or a grab a bottle of wine and then settle in, as I will talk about him for hours. As for the public, it is enough to know we are two imperfect people no longer afraid to show our imperfections. It’s a really good beginning to the story.

Going into this online dating experience, I automatically assumed any person I met was messaging five other people and actively dating three. So, after looking into the eyes of the person I wanted to exclusively invest in, I found myself in the position of wrapping up loose ends. Having been brought up to please everyone and say the right thing, straight-up honesty can be a challenge for me. I think ghosting can happen because of this. Sure, sometimes ghosts are just assholes who slam things around in your psyche, but for many, confrontation is way harder than simply vanishing into the night. Because I wanted to make a new start in life, and because I’m morally opposed to ghosting, I strove to be upfront with the guys still moving about on the other side.

When detaching myself from these men, I also wanted to avoid bread-crumbing. I didn’t need any followers while the Lumberjack and I blazed this new trail. It can be easy to slip into bread-crumbing if you want people to see you as a nice person. You might even see it as letting someone down gently, but in reality, it just prolongs their pain or postpones their anger. As a former people-pleaser, a huge step in my recovery was sending messages to the remaining men in a clear way, so as not to inadvertently lead them on.

Thus began my series of ‘breakup’ messages. I began with my most recent interactions and worked my way back. Some of the men I hadn’t heard from in a while, so I assumed they’d also found someone to invest in.

On our second date, the Lawyer had made me dinner, walked me back to my hotel, and had given me one of his six thousand books to read. It was a novel in German and would likely take me months to read. I’m the kind of person who writes her name on the flyleaf, just to help people remember to give it back, and having joked with the lawyer I was an international book thief, I didn’t want to have the novel in my possession after we severed ties.

I took a deep breath and composed a message that said I met someone with whom I had a deeper connection, and I would return the book to him immediately, unless he’d be okay with giving me more time to read it. The Lawyer responded right away. He told me he was happy for me, and he also felt a deeper connection with the other woman he’d been seeing. He’d like to stay friends (especially since we’re both new to the city), and I should keep the book. I hope we do stay friends and that he has success with his love interest. So far, so good.

Next was the Italian. I wasn’t sure what to expect. On one hand he was a positive, happy sort of person. On the other hand, he did have the passionate side — and passion can be either good or bad. He had lobbied hard for me to come visit him, and the people-pleaser in me was telling me how disappointed he would be. I knew it shouldn’t matter what he thought of me. It was overcoming my own hang-ups that was the real problem. Again, I took a deep breath, sent the message and waited. Within five minutes he answered with his typical, cheery outlook. He said he was happy for me. *smiley face. He said it was “no problem at all” because he had “a long queue.” *angel face *wink. At this point, I had to* lol. Of course he had a long queue. I was two for two.

Mr. Labrador was last on my list. Having been bolstered by my first two successful relationship shifts, I expected him to have a similar outlook on the situation. I was wrong. He was pissed off. Hurt. He couldn’t believe I would do this to him. On his birthday! (I had no idea it was his birthday — god, I have the best timing).

It dawned on me we had never talked about online dating, or the fact I was seeing other people. Plus, I really didn’t know if he felt anything for me romantically. Three dates, and I felt like a colleague from work, not a lover. Even if he had felt a spark, my feelings weren’t quite there. I certainly wasn’t taken with him enough to be exclusive. It turns out Mr. Labrador was, in fact, a self-described old-fashioned kind of man. He said I shouldn’t be “walking on two lines.” This was hard for me because I was the asshole in this situation, and nobody likes being the asshole — especially me. I think of myself as a sweet mid-western girl, not some trollop toying with men’s emotions.

Clearly, we had a breakdown in communication. I should not have assumed he would be parallel dating; and he should not have assumed I was exclusive. The texts became quite hostile on his side, and I did my best to clarify my position. In the end, he said he was angry and disappointed, but I should call him in a month to go for a walk together.

Fat chance.

I’ve had enough righteous anger in my life.

I’ve learned if you do step through the looking-glass into the world of online dating, it’s best to discuss how odd the scenery is and how strange the characters are. It’s important to find out if East is West or Down is Up, so you can read the map together. If I had done that with Mr. Labrador, we would have learned right away we weren’t suited for each other.

I’ve also had to overcome my own shadows through this experience. I’ve had to practice being myself — to be honest and open, even when it’s hard, and even if it means possibly losing someone. To disappoint someone is not a reflection of me as a person: it’s a misalignment. It’s easy to acknowledge this intellectually, but putting your money where your mouth is can be tough.

I’m happy to say the Lumberjack and I have discussed this bizarro-world, and what it means for us. We are absolutely clear about where we stand and the direction we’d like to go; and we are honest about our shadows and demons. Fortunately, our compasses read the same, and we can take this journey together, step-by-step.

The Lumberjack and I may have met on the other side of the mirror, but we have stepped through to the real world, hand-in-hand.

I’m looking forward to seeing where we go from here.

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Keri Lewis

Writer, adjunct professor, and cross-fitter with a lust for adventure. Life partner to a Labrador. Have my latchkey and PTSD. Proudly Gen X. But who cares?