Love The Dud[e]s Travel


February 3, 2020

Continuation from Sleeping with Regret

Jake and I hit it off and began dating in early 2007.  There was a lot to like about him — especially his mind.  He was an independent thinker and although I considered myself a thinker as well, Jake constantly stretched me to see things from new angles.  He listened to NPR and a bunch of brainy podcasts.  He was cultured, well-read, educated, never married, no kids.  Win, win, win.  He was stationed in St. Pete when we met and was completing his last 6 months of duty there before he’d be moving to Rhode Island for his next duty. 

*****I want to break here to say something.  I wasn’t looking forward to writing about this chunk of years, or about my relationship with Jake. I worried it would be a total downer, and who wants to read that?  I’ve accused Jake of being a narcissistic asshole. I’ve talked some serious trash about him. 

As I began writing, something prompted me to read through my old emails with Jake.  I’m one of those people who never deletes an email (I just buy more storage, judge me) – so there were hundreds of exchanges to sift through. 

As I read through them, I was struck by how immature I sounded. 

Jake wasn’t perfect – he made some big mistakes with us.  But I wasn’t innocent.  All these years, I’ve held onto a narrative that Jake was this awful guy who I was in a twisted relationship with.  I made myself out to be the victim of a self-centered narcissist who never really cared about me.  Looking back, I realize that I acted like a martyr.  The question I’ve had to ask myself is: if he was so bad, why did I stay with him for so long?

The answer is: he wasn’t.  He was actually great in many ways.

I read through those emails today with a fresh perspective and the ability (and willingness) to examine where I went wrong.   I was hard on the guy… really hard.  And I can see where these massive breakdowns occurred because we simply communicated differently and had strikingly different personalities.  In the past, I’ve reflected on this relationship with disdain – even vitriol – like it was this horrible experience. And that simply wasn’t true.

I realize my immaturity in crafting and clinging to a false narrative for all these years.  Truthfully, Jake was instrumental in helping me step into my own.  As you’ll see, he ignited a sense of adventure and fierce independence in me.  He challenged and stretched me, and many times, that pissed me off.  But I experienced a rapid period of growth as a result.

People enter and exit our lives all the time, and none of it is by happenstance.  We jump onto one another’s life paths to help each other, challenge, test, love one another.  We are instrumental in other people’s growth, as they are in ours.  Jake was very instrumental in mine and I have a new respect and love for the time we were together.

I have to say, that’s really nice.  It’s like I let go of some unnecessary baggage I’ve been dragging around for years.  I finally took a look at what was inside of those bags and realized the contents weren’t what I thought.

I looked Jake up on Facebook today after I read through the emails, wondering how he’s been.  He’s married with two little kids – he looks happy.  And that made me happy to see.

So, I wrote about Jake with that fresh perspective.  I’m not wearing rose-colored glasses (you’ll see that as well), but I did have a gut-check with myself.

Now, let’s continue.*****

Jake was an avid cyclist (both road and mountain bike), so I took the money from my tax return that year and bought a road bike.  Riding became a strong bond for us.  I’d get off work on Friday, run to my apartment to pick up Chloe, my bike, and an overnight bag, and head to St. Pete.  We’d spend the weekend riding bikes, laying on the beach, listening to the Wall Street Journal podcast, trying out local restaurants.  I fell in love with St. Pete and was beginning to also fall in love with Jake.  I’d stay at his place until Monday morning and leave early enough to get home, drop Chloe off, and make it to work by 7:30.  He became a respite for me.

Things at my job never got better, so I attended the teach-in that spring, a mass teacher hiring event held in Florida each year.  I took a sick day to attend.  I participated in a couple of interviews and was hired on the spot by a stylish, straight-shooting woman who was principal of a high school the next county over.  That August, I’d have a new job.  Because the school I currently worked at was year-round (no summers off), I planned to tough it out over the summer so I could keep my paycheck and then move in the fall.

But…I ran into the administrator of my current school as I left the teach-in.  I knew she saw me and was pretty convinced I was screwed.

I was correct.

A couple weeks later, she called me into her office to let me know they would not be renewing my teaching contract.  I wasn’t exactly shocked by this news, but I was shocked to learn it meant I’d have no job to return to the next day.  I asked her when my current contract was up and she said, “Today.”

I looked at her for a moment while the news sank in. I was being let go with no notice.  She told me I would receive my last paycheck the following week, via direct deposit, and then asked if I needed a box to gather my things.

Truthfully, I was ecstatic to know I’d never have to walk through the doors of that place again.  But considering I lived paycheck-to-paycheck and had about $200 to my name, I was also panicked.

That night, I drove to Jake’s place and told him what happened.  He was matter-of-fact, maybe too matter-of-fact at times.  Empathy wasn’t exactly his gift.  But positivity and problem-solving were.

“Well good!” he exclaimed.  We were sitting on the couch in his little beach condo and I’d just finished telling him how stressed I was.  I loved his place – he’d rented it fully furnished from an older couple. The beachy decor was so tacky and over-the-top that it was cute. I pulled a Kleenex out of the tissue box on his coffee table.

“Good?” I asked, dabbing the Kleenex under my eyes.

“Yes!” he said.  “That place is a joke.  You hated it.  This is great news!”

I couldn’t help but feel a little relieved by how carefree Jake seemed.  I was panicking about just being fired, and he thought this was cause to celebrate.

“Plus, you already have a new job lined up for the fall, right?”

“Yes,” I replied.  “The problem is, I won’t have any income over the summer.”

“So what?” he asked.  “Collect unemployment for a couple of months.  Really, Jessica, who cares.  Life’s too short to get upset about losing a job you hated.” 

I laughed.  “Jake, I could barely survive on a teacher’s salary.  There’s no way I could pay my bills with unemployment, alone.”

Jake took a sip of wine and got up to turn on some music.  His tastes were eclectic, he was always exposing me to new things.  He started singing along to a jazz song I’d never heard before. “Come,” he said, motioning for me to come to him.  I smiled.

“What do you want?” I asked playfully.  He pointed to me, and then to himself.

“I want you to come over here and dance with me.”

“Jake, you’re nuts.  I don’t know how to dance to jazz.”

“Me either,” he said, grinning. “Come,” he motioned again. “We can make it up as we go.”

I stood up and hesitatingly walked toward him.  He reached out to grab my hands and swiftly pulled me close.  “Sometimes, Jessica, it’s fun to not know all the details of your next move.”  He held my hand in the air and spun me around as I laughed.  “Like that, you see?  Embrace the adventure, hot stuff.  It will all work out.”

And it did.  I put my stuff in storage and joined Jake on a cross-country adventure that summer.  He was going to visit his family in Indiana, do some cycling in Colorado, drive to California, and then return to Florida to move his things to Rhode Island.  I flew to Indiana to meet his family and visit for a week.

I had to return home to take care of some paperwork for my new job while Jake drove to Colorado.  A week later, I flew to Colorado and he picked me up at Denver International Airport.  The airline lost my luggage and I was told they would have it the following evening.  Jake and I drove to a house he owned near Fort Collins.  I called the airport the next afternoon to see if my luggage had arrived.  Upon confirmation, I let Jake know. 

“They have my suitcase, we can go get it now.”

Jake walked over to the table, picked up his keys, and handed them to me.

“What?” I said.  “You’re not coming with me?” 

“You don’t need me to go with you,” he said.

“Yes, I do,” I protested.  “I don’t know how to get to the airport from here, it’s a long drive.”

“It’s only an hour away, Jessica. You can do this.”

“What if I get lost?” I asked.

“Use the GPS,” he said.  “I’ll be here if you need to call.”  I looked at him blankly.

“Are you being serious right now?” I asked.

“Sure am,” he said as he returned to the couch and picked up the book he’d been reading. 

I was pissed.  I didn’t understand what his problem was.  I grabbed my purse and left the house, slamming the door behind me to make sure he knew how pissed I was.

I drove to the airport, picked up my suitcase, and returned to the house without a problem.  I was still mad at Jake when I got back so I didn’t talk to him. That’s how 24-year-old Jessica dealt with conflict.

We were laying in bed later that night, neither of us asleep.

“You still mad at me?” he asked.  I didn’t respond.

“I’ll take that as a yes.”  I stared up at the ceiling, still stewing.  Jake sometimes called me a volcano, which was a pretty accurate description of how I handled negative emotions back then. 

“I think you’re overreacting,” Jake said. 

“I think you were being a jerk,” I replied.  “It’s not like you had anything else to do.”

“I wasn’t being a jerk, Jess.”

“Sure felt like it.”

“You’re off then,” he replied.

I snapped back, “Stop invalidating my feelings.”

He was quiet for a few minutes.

“Jess, I’m going to say something.  And it will probably make you mad, but it’s not meant to.”

“I’m already mad,” I said.

“Yeah,” he replied. “I know.”  He waited another minute, gathering his thoughts. “Jess, you’re one of the smartest and most capable women I have ever met.  I don’t think there’s anything you couldn’t do.”  He paused again as I waited for the but.

“But I don’t think you realize it.”

“What’s that supposed to mean?” I snapped.

“Well, think about it, you got totally bent out of shape because I made you drive to the airport without me.”

“You knew I didn’t want to go alone,” I interrupted. “But you didn’t care.”

“That’s where you’re wrong.  It wasn’t about whether or not I cared.  You know I care deeply for you.  I just want to help you step out of your comfort zone more,” he said.  “I want you to see how capable you are with things that may initially make you nervous.  I want you to stop worrying so much.”

At the time, I didn’t see it.  I thought Jake was being an insensitive asshole.  But looking back… I get it.  And as much as he pissed me off for doing things like this (it became a regular occurrence in our relationship), I appreciate it now.  Although I thought he was being a careless jerk, his tough love helped me to develop another level of independence and self-assuredness.  I went on to do some things in the next few years that I would have never had the courage to do had I not developed a strong belief in myself.


I got over the airport incident and we spent the next week exploring the foothills east of the Rockies.  I fell in love with Colorado and I didn’t even get a taste of the big mountains (yet).  Next, we drove to Wyoming to visit with a friend of his before heading westward to California. 

It was around 1 in the morning when Jake pulled off the interstate in the middle of Wyoming.  I had fallen asleep but woke up as his SUV slowed down. “Where are we?” I asked.

“Somewhere in Wyoming,” he said.  “I want to show you something.”  He parked in a rest area and opened his door.  “Come on.”

“Where are we going?” I asked.

“Just come.”

I got out. Jake walked around to my side of the vehicle and grabbed my hand.  He locked the truck and after the headlights dimmed, my eyes strained to see anything.  It was total darkness.  “What are you doing?” I asked.

“You’ll see,” he said as we began to walk.  As my eyes adjusted, I could see the faint outline of a sidewalk.  We walked about thirty yards and then stopped.

“Look up,” he said. 

I lifted my head and gasped.  The black sky was dotted with thousands of stars – more stars than I had ever seen in my life. It was breathtaking.

“Oh my god,” I whispered.  “It’s beautiful.”

“Pretty cool, huh?”  He pointed up toward a part of the sky that appeared sort of cloudy.  “You see that cloudy looking streak?”

“Yeah,” I replied.

“That’s the Milky Way.”


“Sure is.”  I felt awestruck. I’d never seen the Milky Way with my own eyes. There’s far too much light pollution in Florida.

“Wow…”  I whispered. I told myself to remember this moment.  “It’s incredible.”  We stood there for about 20 minutes staring up at the sky, identifying constellations, marveling at the expansiveness of the universe. 

This was the part of Jake that I couldn’t get enough of – and it was the part that would keep drawing me back in each time we broke up…

Get Email Updates!

Signup now and receive an email once I publish new content.

I agree to have my personal information transfered to MailChimp ( more information )

I hate spam. I will never share your email address. You can unsubscribe at any time.

    Leave a Reply