On Finding Hope After Heartbreak

As seen on Thought Catalog.

The sugary booze from the night before swirled in my stomach. I did what I always do in this scenario: a few splashes of cold water to the face, baseball cap, caffeine.

I made my way to the lobby. It was no more than a quarter past seven.

“I’ll do an oat milk latté,” I said.

“Twelve or sixteen ounce?” the barista asked.

“I’ll start with twelve,” I replied, knowing I’d be back within the hour for a refill.

I settled into one of the couches in the lobby. The electric fireplace was going even though it was June.

Soft music hummed in the background. The hotel was just waking up, too. I cracked open my book and began making my way through the first chapter, my body starting to shrug off the tequila and rye from the night before between sips of caffeine.

No more than 15 minutes later, he sat down. He had a boyish face and sleek Nikes. We were practically mirror images of one another. He, too, was in a baseball cap. He, too, was reading a physical book. He, too, found himself in the lobby of one of Chicago’s trendiest hotels before 7:30 am on a Friday morning.

I found him cute—very cute. I wanted to talk to him. I hadn’t felt this way about a guy in a while. Four months out from a pretty traumatic breakup, I was still nursing my wounds. It was refreshing to be drawn to someone in this way.

We stole glances at one another for the next 15 minutes. I had a feeling I’d start chatting with him, but I wasn’t sure when or how to begin. I went back to reading my book. Every few pages I’d look up, and at the exact same time, he did the same.

As predicted, around 8 a.m., my 12 ounce latté had been sucked dry and I needed more coffee. I ventured back to the coffee bar.

“What can I get you?” the barista asked again.

I hesitated. I was caught between what I actually wanted and how I was going to start a conversation with this guy. Should I even? Flustered, I ordered a black coffee—something I didn’t even want—and made my way to the side counter to add cream and sugar. As I stirred this coffee I’d later toss, I decided to go for it.

“I don’t mean to bother you,” I said, “but are you reading 1776?”

I’d noticed the title on the spine of the book when I was sitting across from him. Paired with his Patagonia baseball cap and warm demeanor, it was both unexpected and adorable.

“Ha, I am” he replied. “I’m really into American History. What are you reading?”

He reached out his hand. I went to shake it.

“I was actually reaching for your book,” he said with a smile.

“Oh!” I said, handing it to him. I felt a wave of mild embarrassment; had I initiated skin-to-skin contact too soon?

Not wanting to get too lost in the thought, I carried on. “It’s a memoir by one of my favorite writers,” I said.

He scanned the back cover.

We exchanged basics. He was in town for his brother’s bachelor party. I was in town for work. He asked if I was staying at the hotel. I said I was. He made a point to clarify that the weekend wasn’t a “strip club type” of bachelor party. I found that endearing.

Within a few minutes, we’d exchanged numbers and made loose plans to meet up later that evening. I left the lobby with renewed energy, my hangover a thing of the past.

My mind couldn’t linger on the interaction too long. I had a photoshoot to prep for. But three hours later, with images captured and no word yet from my lobby crush, I started to wonder if he’d actually reach out. The anticipation was comforting. It felt good to be excited about someone again.

At 1:25 p.m., he texted: Hey so we’re going to the sushi restaurant near the hotel tonight at 8. So when we’re done around 10 we’re just gonna go to the bars around there. Lmk if you want to come meet us.

I sensed a reserved enthusiasm. What I really heard was: Was that real this morning? Our pre 8 a.m. flirting?

I felt it, too. Was he real? I wrote back: Yeah that’d be fun. Keep me posted.

In other words: Yes, that was real and I’m real. Yes, I’m looking forward to seeing you. In fact, I think it would be fun.

Bubbles quickly appeared.

Will do!

The rest of the afternoon felt a little buzzier. I walked the few miles downtown and made my way to the Art Institute, gliding through the exhibits. When I realized I’d inadvertently landed at the Bean, Chicago’s quintessential tourist trap, I didn’t mind. When my legs got tired, I read in the nearby gardens.

At 8:36 p.m., he texted again. He said they were running behind and was it okay to meet up closer to 10:30? I was exhausted but pushed myself to say yes. I knew having this experience would end up serving me in ways I couldn’t yet articulate.

At 10:32 p.m., he texted to say he was in the lobby. I dragged myself out of bed, checked my cheeks for pillow creases, and got into the elevator. As I was riding down, I realized I wasn’t sure I’d recognize him. My fears dissipated when I saw him standing near the hotel entrance. He’d changed into a crisp white shirt. The baseball cap was gone. I could tell he was surveying the area near the elevator bank.

“Hi!” I said.

“Hey!” he chimed back.

We settled in with the bachelor party, hanging back a few yards to chat. We talked about our meet cute that morning, how it was inevitable we’d end up seeing each other again. He admitted to stalking me with no luck. He asked me if I was sad his hair looked better than mine. He had a Seth Rogan-style humor. Between every word, I collapsed into a fit of giggles. Within a half hour, my face hurt from laughing so much.

We moved from bar to bar, half talking to the group, half not. I felt like I was in college again, trailing along with a big group of guys. Twelve years had passed since I’d graduated, but at 33, I still worried what they thought of me.

After mediocre runs at two bars, we went back to the hotel. We’d reached the point of drunkenness and exhaustion where making conversation was a lost cause. We’d also managed to separate ourselves entirely from the group. After negotiating whose room we’d go to, we haphazardly made our way to his, leaving my credit card and jacket at the bar.

I felt like a teenager as we pawed at each other in the elevator. We arrived at his floor and he took my hand, leading me to his room. I was still laughing. We collapsed into his bed. The next 10 minutes were a mess of mouths and tongues and breathing and thrusting and feeling everything we could feel through our clothes.

Somewhere in there, I turned to him and said, “Robbie, will you kiss my back?”

I didn’t really know what I was saying even as I said it, but I had a visceral desire for a more affectionate physical connection.

I crawled onto my stomach as he placed his mouth on my upper back. I felt my entire body relax. But seconds later, I could tell he wanted to go back to what we were doing before, so I sat up.

Kneeling on the bed, I felt my cheeks grow hot. I cradled my face in my hands, realizing if we kept hooking up, I’d begin to cry.

“Why are you covering your face?” he asked.

I had no words. It was as if the physical grief from my previous relationship had rushed to the surface, moving out of my bones and into the air.

We’d reached a decision point. We were either going to go to my room and not stay in the one he shared with his younger brother or we were going to stop. I knew I couldn’t bring him to my room. I knew I couldn’t go any further without breaking down into a teary mess, a mess I didn’t want to explain. I gathered up my belongings and we made our way back to the bar. I grabbed my credit card and jacket, we kissed goodbye, and he went to catch up with his friends.

The next morning I awoke and reached for my phone, hoping to have heard from him. Nothing.

I showered and packed up my things. I needed to leave a tip for the maid service, so I popped out to the ATM a block away. On my way back to the hotel, I stopped by the coffee bar to grab my latte.

As the barista was making my drink, I asked, “Are you going to be here all morning?”

I wanted to buy a coffee for Robbie. I wanted to leave some sort of token to say, “Thank you.” She said she would be, so I put forth my plan.

“This is going to sound strange, but I’d like to purchase a coffee for a guy potentially coming down later this morning,” I said.

She grabbed a pen and began jotting down his name on the back of an old receipt.

“Here’s 10 bucks” I said. “If he doesn’t show, just keep the money.”

With my airport-bound Uber waiting outside, I didn’t have time to register what she thought of the scenario or what I was really doing. What did I hope to accomplish by treating him to coffee? Why did I feel the need to thank him?

Once through security, I found myself checking my phone every few minutes, making doubly sure I didn’t have it on silent. If a ping went off nearby, my ears perked. I wanted to hear from him. I’d had so much fun. Maybe we could somehow see each other again.

By 10:17 a.m., I caved.

Did you get your coffee?

Not a word.

As I waited for my plane to take off, I texted back and forth with my friend Meredith about what had happened. I told her how we’d met, how it felt, and why I’d elected not to sleep with him.

I’m so emotionally raw, I’ll cling to anything within a 10 foot radius, I texted.

Totally, she wrote back.

Meredith got it. Meredith had dropped her apartment keys into my hands the night of my breakup. Meredith had been on the receiving end of many tear-filled phone calls during the aftermath. Meredith knew I could have easily slept with Robbie, but that I wasn’t ready. I could handle a make out session, not a one night stand.

Gone were our days of haphazardly hooking up with guys and hoping they’d turn into husband material by morning. We not only knew better, we cared for ourselves more. As we’d gotten better at navigating these nights out, we’d also gotten better at understanding what they stood for. How, if handled with care, these weren’t just random run-ins but experiences that taught us more about ourselves.

Every encounter adds a marble or two to the jar, Meredith wrote in response to my tangle of emotions. I used to pick up each marble—each of these encounters—and hold on to them, plagued with questions like: ‘Do they like me?’ ‘Will I see them again?’ ‘If I don’t hear from them what does this mean about me?’ Now I see each encounter as an addition to the jar. Each guy, each experience, gives me insight into who I am and what I want. The marble is a lesson, not a mini-heartbreak.

Our texting banter ended as the plane began to take off. I tilted my head back and closed my eyes. I realized in that moment I didn’t really care if Robbie texted back. It didn’t matter if we ever saw each other again. What mattered had already happened. The coffee had been a prop. What I’d really wanted to say was this: “Thank you. Thank for waking me up. For holding my hand and breathing life back into my body. For making me laugh more in one night that I have in the past year. For giving a part of myself back to me. Thank you.”

I gratefully put this marble in my jar, and with that, did my best to let him go.