Dating Love The Dud[e]s

Opposites attract

March 17, 2020

Continuation from Jake… (the pic above is from 2009, when I was in DC with Jake. He picked a flower and stuck it behind my ear while we were strolling downtown one evening).

I loved the western part of the country.  It’s vastness and openness, the opportunities to really feel like you’re in the middle of nowhere, to soak up the silence and the beauty of Mother Nature.  Jake and I made our way out to California and then headed back.  We’d been together for six months but had not yet exchanged the L-word.  I loved him but I was too chicken to say it first – I still am.

On his last day in St. Pete, Jake walked me out to my car.  I’d helped him finish packing up and cleaning his condo, and he was about to leave for Rhode Island. 

I was saddened by this.  He’d no longer be an hour’s drive from me – now he would be a couple hours away by plane.  He was going to be in Rhode Island for a year and hoped to secure his next job in DC.  We hadn’t worked out any details, but we did decide we wanted to stay together, to try to make the distance work.  I leaned against my car as he stood in front of me.  I could feel my eyes tearing up but I didn’t want to get emotional.  Then I looked up at Jake and saw tears in his bright blue eyes.

“Whoa, whoa, whoa,” I said. “You’re not allowed to cry.”

“I’m not,” he said, wiping his eyes. “This just sucks.”

I hugged him.  “I know.”

Up to that point, I had no idea Jake would be that upset about leaving.  He was good at keeping his feelings under lock, which had made me feel a little insecure about our relationship.

“I’ll miss you,” he said, clearing his throat.

 “I’ll miss you too,” I whispered.

He pulled back with his hands on my waist and looked at me.  “I do love you, Jessica.”

I do love you.”

It was like he thought I assumed he didn’t love me.  My heart jumped in the way it can only jump when someone you love first utters those words.  I stood on my tiptoes to kiss him.

“I do love you too,” I said. Minutes later, I got in my car and headed home, and Jake began his drive up to Rhode Island.

I started my pre-service teacher training at the new school a couple weeks later.  I was assigned freshman English.  It was a public school, so the format was completely different from the last school I’d taught at.  And by completely different, I mean I actually got to teach.   I had an amazing principal who granted me autonomy in the classroom – I didn’t realize it at the time, but in a world of ridiculous educational policies and so-called accountability measures, this was huge.  She allowed me to make up my own curriculum to hit the benchmarks my students needed. 

I also adored my students.  Freshmen were quirky and awkward.  They hadn’t yet gotten sucked into that too cool for school thing that happens to most of us in high school (except me – I assure you, I was never cool).  I am blessed to say that I’ve stayed connected with many of them over the years. It’s wild to think that my former students are now the age I was when I taught them – where has the time gone?

I got an apartment in Orlando and discovered a huge cycling community there.  Jake was the only person I’d ridden with up to that point.  I wanted to start trying some longer rides and I thought it might be fun to be part of one of those huge groups of cyclists I’d regularly see when I was out riding by myself.  I joined an online forum for one of the local cycling clubs and started a conversation with Greg, a guy in his 60s who seemed to be one of the few men on the forum who was open to riding with a woman.  I hadn’t yet experienced the ego mania that’s prevalent among male cyclists (to be clear, not all male cyclists are egomaniacs).  Anyways, Greg invited me to come ride a century (that’s an organized 100-mile ride) in Gainesville with some of his Orlando crew. 

I was stoked.  I met Greg and his cycling buds in the parking lot and did my first century.  I was hooked – not just on long distance cycling, but on hanging out with a group of upbeat, friendly people who also loved riding.  Cycling quickly became a centerpiece in life.  I’d rush home after work and hop on my bike to get in as many miles as I could before sunset.  My weekends were centered around riding.  Greg would organize rides with a few other people and we’d be on the road at the crack of dawn, riding all over Orlando, Clermont, and the surrounding areas.  We’d usually find somewhere to stop for a late breakfast or early lunch, and then stop again for a beer on the way home, paying no mind to how sweaty and dirty we were. 

Things seemed to be coming together in my life.  I knew teaching wasn’t going to be a long-term career for me, but for now, I had a job that I enjoyed, which paid me enough to have a tiny bit of money left over after the bills were paid.  I was getting out, enjoying life, meeting other cyclists.  I even became friends with some of the teachers in my hall.  I no longer felt the constant pang of loneliness. 

In fact, cycling became so central to my life that I even started riding my bike to and from work, which was about 35 miles each way.  I bought a headlight, studded the back of my bike with blinking red lights, and braved the roads of Orlando before sunrise. 

Jake and I were doing the long-distance thing, taking turns visiting each other.  The distance was hard and miscommunication became commonplace.  I learned how difficult it is to keep clear communication with someone over text and email.  I started to notice some of our incompatibilities around this time.  Jake had such a dominant personality that sometimes I felt like I faded into the background when I was around him.  He also tended to act fatherly toward me – not in a protective manner, but in a teaching-me-about-life-manner.  I started to feel like around him, I would wilt a little.  I’d been creating this new life for myself in Orlando and Jake and I were in a long-distance relationship that felt like a fantasy.  Every time we saw each other, it was like being on vacation. 

I’d look forward to our time together, but the distance started to make us crack.  We miscommunicated.  I’d get upset.  Then we’d get into an argument. 

Despite these issues, I was magnetically drawn to Jake.  The things that pulled me in – his gregariousness, his intensity – were also the things that challenged our compatibility.  Jake was blunt, to the point, and would often come across as insensitive or callous.  At the time, I’d get my feelings hurt and question his love for me.  To him, someone who went to a military academy, was an officer in the military, and grew up with three brothers – he wasn’t being abrasive.  This was just how he communicated. 

Jake was curious, an intellect.  He was the type of guy who would go to a museum and get one of those sets of headphones for a guided tour, listening intently and learning everything he could as he roamed through the exhibits.  He had a zeal for life that I didn’t understand or relate to at the time – but wanted to.  His curiosity never failed to lead us on an adventure somewhere.  I was envious of the lens that Jake seemed to always view life through – like it was one big adventure that should never be taken too seriously.  He was great at thinking on his feet and problem-solving, and he never seemed to worry when things didn’t work out as planned because he knew one way or another, they would work out. 

I remember riding bikes with him in Orlando one afternoon when he was down for a visit.  We were about 15 miles from my apartment, out in the country, when a nasty thunderstorm rolled up on us.  Huge, angry raindrops pelted us as lightning bounced around the black skies.  We huddled under a bridge together as we waited for the storm to pass.  But after nearly an hour – it was still pouring. 

“I say we flag someone down and ask them to give us a ride back,” he said.  We were both wet and cold.

“What about our bikes?” I asked.

“Just hide them in the bushes – we can come back in your car and pick them up.”  I was horrified at the thought of leaving my beloved bike hiding in the bushes, sure that someone would steal them.

“You think they’ll be okay?  What if someone takes them?”

Jake chuckled and shook his head.  “They’ll be fine, Jess.  Do you have another suggestion?”  He had a point.  Neither of us had our phones and there was no telling how much longer it was going to storm.  Plus, we had less than an hour of daylight left.  So Jake flagged down a car, convinced a nice couple to drive us back to my place, and then we came back and got our bikes.  Nobody had stolen them.  It was fine. 

From Jake, I also learned that I didn’t need to always look like a beauty queen.  He made me feel like he thought I was beautiful whether we were dressed up for a nice dinner, or sweaty and dirty after a long ride.  I stopped wearing much makeup.  I became more comfortable in my natural skin – and body.  As someone who had struggled with body image and dysmorphia since elementary school, calories and dress size were two things that constantly plagued my mind – Jake was the first boyfriend I opened up to about these things. 

I remember visiting him in Rhode Island in the early spring.  I had put on a couple pounds – nothing major, but enough to make my size 5 jeans snug and prompt a total mental spin-out.   The barrage of negative self-talk began and I felt powerless against it.  Jake could tell something was wrong as we strolled around downtown Newport.  It was a beautiful, cool morning, but I couldn’t enjoy it because I was consumed by the snugness of my jeans.

“What’s going on?” Jake asked. 


“We both know that’s a lie, Jess.”  I could feel myself tearing up.  Jake looked over and saw I was visibly upset.  “Hey…” he said, grabbing both my hands and stopping us in the middle of the sidewalk. “What are you so upset about?”

I didn’t want to tell him.  I’d never talked about my inner battles with my body to anyone.  It had been evident from years when I was rail-thin during the peak of my eating disorder… but even then, it had been my silent battle.  I secretly wanted to share it with someone.  I thought that maybe by vocalizing it, I’d shed light that could help it start to dissipate…but the thought of talking about it was also overwhelming.  I looked up at Jake, blinking away tears as he squeezed my hands.  “Let’s go back to the condo and talk.  How’s that sound?”  I wiped my eyes and nodded.

When we got back to his place, he listened intently as I talked openly about my gremlins.  I told him that I’d been triggered by my tight jeans.  He looked at me in disbelief.

“Jessica, you look incredible.  Your body is amazing – I can’t fathom how you can’t see it.” 

“You have to say that,” I said, reaching for a tissue to blow my nose.  “You’re my boyfriend.”

“No, I don’t have to say anything, Jess.  This isn’t lip service.  You have a body that women would kill to have, and that men would kill to be with.”  I shook my head in protest.  “Don’t shake your head, it’s true.  I’m upset that you would feel this way about yourself.  You’re beautiful,” he paused.  “But the part that bothers me the most is all the stock you’re putting into your body.  As physically gorgeous as you are… and you’re gorgeous… it doesn’t compare to what’s up here,” he said, tapping my head.  “You’re brilliant, too.  And you’re kind.  You’re compassionate.  You have an ability to empathize, a sensitivity that is beautiful, too.”  He leaned forward to kiss me.  “You’re the total package, Jess.”

“I used to feel it, when I was stripping,” I said.  “But lately, I don’t.  It’s like all my old insecurities about my body have resurfaced now that I’m not flashing my body to total strangers anymore. I don’t even know what to make of that.”

“That makes sense,” he replied.  “Think about it – when you were dancing, you had constant validation from men about how beautiful and sexy you are.  It’s not that these self-doubts disappeared, but the constant affirmations silenced them.”  He reached out to wipe a tear from my cheek.  “Maybe I’m not doing a good enough job of telling you how sexy you are to me,” he said.  “I can do better.”

“No,” I said.  “I don’t want you to feel like you’ve got to constantly tell me how beautiful you think I am to combat this narrative in my brain.  I want to get over this on my own.”

“And how’s that working out?” he asked. 

He had a point.

“Maybe you need to dance for me,” he said.  I laughed.

“Of course that would be your solution.”

“I’m serious,” he said, “maybe it would help.”

“I’m not dancing for you – not when I feel like a beached whale.”  He stood up and grabbed my hands, pulling me up from the couch.

“Please,” he said.

“Not a chance.”

“Would it make you better if I got naked, too?” I laughed and playfully pushed against his chest.

“You’re ridiculous.”  He took off his shirt and tossed it on the couch. 

“There, is that better?”  Now I was giggling.  “I have an idea; I know you’re turned on by rugged military guys.”  He stood up and went into his bedroom, returning with his dog tags and a pair of aviator sunglasses.  He sat back down on the couch, put on the glasses, and slipped the dog tags over his head.  He leaned back, resting his arms on the couch cushions.

“There, how’s that?” he asked.  “Am I sexy enough for you now? Do you want to do dirty things to me now?”

“You’re so dumb,” I said, smiling.

“I am,” he said.  “Now take off some of those clothes.  I’ll crank up the heat if I need to, so you have no choice.” 

I sighed and sat down to take off my shoes.  “This is absurd, you know.”

“I don’t care,” he said.  I slipped off my jeans and stood in front of him with my hands on my hips. 

“There,” I said.  “Happy?”

“Nope.”  He tugged at my sweater.  “Off.”

I shook my head and sighed, taking off my top and setting it down on the couch.  As I stood in front of him in just my bra and panties, I watched him scan my body from top to bottom.  “You’re fucking amazing,” he said.

“Ugh, no…” I started.

“Shush,” he said, reaching up to cover my mouth.  I rolled my eyes.

“Now what?” I asked. 

He smiled and reached for his phone to turn on some music.  “Now,” he said as he thumbed through his Pandora stations, “now you dance.” 

Jake’s response to me that day was perfect and I loved him for it.  We weren’t perfect – we’d argue, we’d miscommunicate, we’d break up for a day or two… but we always ended up back together.  As my second year of teaching came to a close, Jake’s time in Rhode Island was ending and he was preparing to move to D.C.  He moved that summer and I spent a lot of time with him in his new basement apartment in Eastern Market, exploring the city with him. 

The following fall, I started my third and final year of teaching.  At this point, Jake and I had been together for almost two years and we’d started discussing our future together.  We talked about getting married, having kids, and how my career would always come second to his because we would be consistently moving for his military career.  I was bothered by this, but I didn’t exactly have much of a career of my own.  I enjoyed teaching, but didn’t feel like it was my calling.  I just didn’t really know what my calling was.

Jake knew people in high places in D.C. and called me one day to tell me that he’d secured tickets to watch the symphony at the Kennedy Center – and we’d get to sit in the president’s box (as in, President Obama).  I was tickled.  He tried to casually ask me my ring size, as if that’s ever a casual question to ask a woman. 

I knew he was going to propose that night.

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