Bro Cruise Disaster

I had started talking to Emily at the beginning of last summer and I was, despite my every attempt not to, falling head over heels for her. By all available evidence at the time, it appeared she was also quite smitten with me. It was gross. Suddenly my texts had emoticons of hearts and kissy faces and flowers and animals—I didn’t even know what half the emoticons I sent meant, but I felt compelled to send them. “I like you a lot, more than words can convey, so here’s a winky face, a lizard, a glass of wine, and fireworks?” I had become everything I hate and am afraid of. I’d be minding my own business, sending important emails at work and all of a sudden she’d pop into my mind. It was really annoying and also kind of nice.

Emily and I first met online. OKCupid said we were 57% compatible and 23% enemies, leaving a mysterious 20% unknown. I probably should have taken that as a red flag. But she was drop dead gorgeous and had a picture of her dressed as Princess Leia in her profile—how could I not want to meet her? What do silly computers know, anyway? Our first exchange was really awkward, another red flag. She had messaged me her phone number over the OKCupid app and I had tried to copy her number, but after tapping it with my finger, my phone started dialing. I panicked—I had not meant to call her within seconds of her sending me her number. It was too late, a smooth “Hello?” in a southern drawl, greeted me through my phone’s speaker. I cleared my throat and tried to play it cool, “Hi, it’s um, Jay, um, from OkCupid?” She laughed what sounded like a nervous laugh and said “Well that was mighty fast.” Shit. I stuttered an explanation about clumsy thumbs and we continued our conversation. Upon discovering I worked at the local LGBT center she asked “Wait, are you GAY!?” My first instinct was to be sarcastic and say “Yes, I’m an out gay man who poses as a straight man on internet dating sites in my free time.” Instead I said, “Pretty sure I’m not.” Now, I could have at this point clarified that my connection to the LGBT community was that I was a transman, but I was too nervous to think that clearly. (I did later in a much more awkward exchange inform her—but that’s another story, entirely.)

That first phone call lasted over an hour. I found out she was working as an actor at a local summer stock theater. Coincidentally, my friend and I had already planned to see Mary Poppins at this theater the very next day. She invited me to stay for the after show bar show. We agreed to meet up before the show. When my friend and I arrived, I was nervous and wanted to forget the whole thing. We walked into the bar area and I saw Emily across the room. I did what came naturally, I turned and sat down at the opposite side of the room, like I was a boy at a middle school dance. I should mention that Emily looked very different than the photos on her dating profile. Mainly because she was covered head to toe in gray paint. In fact, the only identifying features were her blue eyes and her perfect smile.

As the weeks went on we continued talking and texting and seeing each other as often as we could. Her schedule was very busy because during the day she was rehearsing the next show and at night she was performing the current show. To spend time together I found myself at the theater a lot or squeezing a quick meal with her during her dinner break or going out with the entire cast to celebrate a good show. Finally, after a month she got a day off. I wanted to take her on a proper date, one that would be cheesy level romantic and memorable. I knew we had a limited amount of time together, she lived in New York City during the year and this was likely a Grease-style-summer-fling (“oh oh those summer nights”) so I wanted our moments to count. And, also, as I indicated above I had totally lost my mind and was not acting like myself at all. So I began to plan a surprise date for her.

If previous posts have not already alluded to this, I am not a smooth or lucky guy. Things do not often go my way. (Spoiler Alert: This story doesn’t break this trend.) I picked her up in my orange Honda fit, which had the passenger side mirror (sans mirror) duct taped in place. It was a very hot and humid day and the duct tape had started to melt. We didn’t make it 2 miles before the mirror came untaped. It hung limp by an electrical wire, flying up and down as we sped along, occasionally making a startling thud as it collided with the window or door. She looked at me, unimpressed, and laughed, “Seriously?” I pulled over at a gas station and reapplied fresh non-melted duct tape to secure it back in place. I said a prayer to the game and dating gods, and resumed. I had to stop and reattach the mirror two more times on our 45-minute drive to our first destination, the beach. I exhaled and hoped we could continue the day with all of that behind us.

taping my car back together

Next was dinner which ended up a disaster. The food was terrible and our server was a little too friendly and asked a lot of questions. She seemed to be under the impression we were a long-time couple and had lots of questions neither of us knew the answer to. “What are you celebrating tonight?” “How did you two meet?” “What kind of beer does she usually like?” “Where are you two from?” At the end of dinner, she slipped us a dessert in a to-go bag with two forks and I immediately felt bad for disliking my food and cursing her in my mind for all her invasive questions.

After dinner was the big surprise. I had scheduled a sunset cruise on Lake Michigan for us. They allowed you to bring your own wine or beer and sailed you off into the sunset for an hour long tour. I was super proud of myself. I was about to prove to myself and everyone that I could be romantic and suave. More importantly, I was going to sweep Emily off her feet! Most memorable date, here we come! Well, I wasn’t wrong. I don’t think Emily will ever forget this date, even if she gets amnesia.

We pulled up to the address they had emailed me with my confirmation. There was no identifying office or boat or anything in view that provided any clue as to where we should go. I couldn’t ask Emily since she still had no idea where I was taking her. I pretended to be confident and started leading her to the first dock I saw. Docks had boats. And clearly our sailboat, the Elsie J would be labeled and visible from the dock. It would probably be written in gold script and a polite captain named Stefan would wave and greet us; “Cheerio Jay and Emily, welcome aboard the Elsie J. She’s a fine ship and the water is perfect for a romantic sunset cruise.” Emily would squeal with delight and smile while looking at me with her sea blue eyes. “You shouldn’t have!” she’d say while hugging me tight. We’d board the ship and head off into the sunset. “They lived happily ever after” would appear in white script across the screen and credits would roll.

Instead, we rounded the corner and a mismatched group of bros were sitting in metal patio furniture. A rough looking man with sandy brown hair and a black rain jacket reached out his hand asking, “Are you Jay Maddox?” with a chewed pen dancing at the corner of his mouth. Startled and suddenly hesitant I said, “Yeah. Well, actually it’s Maddock with a—nevermind, yeah that’s me.”

“Great! Everyone’s here! I’m Dave and I’m your captain, let’s go through the safety precautions and board the great Elsie J!” he yelled, unnecessarily since we were all in a small circle and could hear him fine.

Emily looked at me with a mix of worry, confusion, and a dash of anger. Through gritted teeth she whisper-yelled, “What. Is. This?”

I smiled in an attempt to ease her worries, “It’s a sunset cruise! Tah-dah and surprise?” I whispered uneasily.

As I tuned back into Dave’s safety instructions, I heard the words “Tug” and “Boat” as in a tugboat. No. No. No. This was supposed to be a sunset cruise on a SAILboat. Tugboats didn’t cruise across open water into the sunset. Tugboats were not romantic. Tugboats were not part of this plan! I looked at Emily, worried she had also heard Dave say that Elsie J was a mighty tugboat used for whatever purposes tug boats served up until a decade ago. Based on her curling lip and scrunched up nose, she had indeed heard Dave say just that AND she was not pleased.

We boarded the Elsie J and all her tugboat glory. Aside from Captain Dave, our company for the next hour comprised of a mom, a teenage girl (who looked less pleased than Emily), a young boy, a dad wearing a fedora, three 18/19-year-old boys, and a Hawaiian shirt clad Colonel Sanders (the KFC guy). Once we cruised out awhile, Dave said we could go up top. Emily and I climbed up to the top of the boat and sat down on some blankets. We cracked open a couple beers, clinked bottles, and I saw her smile. I exhaled. Maybe this could still be saved.

Then Colonel Sanders, the three boys, and the dad climbed up top as well. There was   silence as they stiffly looked out at the water and the sunset, keeping an arm’s

all the bros and me on the Elsie J

length between each of them. I looked at Emily and she mouthed “What is happening?” Emily and I started laughing hysterically. Here we were on a fifty-year-old tug boat tugging along Lake Michigan with a KFC founder look alike and the bro-iest of bros, on what was technically our first date. We made the best of it with uncontrollable laughter through the majority of that hour long adventure. We coined the date #brocruise2015 and I promised not to plan anymore surprise dates the rest of the summer.


#BroCruise2015 ended here, but the story of Emily and I did not. (Spoiler Alert: I kept trying to impress her with disastrous results.) This post is an excerpt of the complete chapter of Emily and I that will be included in the full book.


Next Post: Deal Breakers

Previous Post: The Presidential Date

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