Chapter 27

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It was always tough to tear my friend Kyle away from his studying to do things other people would consider important, like, for example, eating. But tonight, we’d successfully extracted him from his books, and he, Brad, and I were sitting in the cafeteria ingesting calories and swapping stories about high school relationships. I told them a little about Francesca and Evelyn.

“So what did they say?” Kyle asked.

“When?” I replied.

“When you told them you liked them?”

I laughed. “Yeah, right! I could never tell them I liked them! You know how much risk of rejection that is?”

“Dude,” said Kyle, brushing blond curls off his forehead. “You’re telling me you’ve never had a DTR?”

“A D-T-what?”

“A ‘define the relationship’ talk. Where you tell a girl you like her. You talk about whether you two want to be together. That kind of stuff.”

“Um, nope.”

“Did you kiss either of them?”

“No, of course not. I’ve never kissed anyone.”

“Yeah, that’s probably why you’ve never had a girlfriend. Brad, back me up here.”

“I’m with Kyle,” said Brad, leaning forward. “If you never tell a girl you like her or make out with her, I mean, how’s she going to know?”

I stroked my chin. “But what if she doesn’t like me?”

“It happens,” said Kyle. “That’s life. But if you don’t have a DTR, you’re never going to know if she likes you, too.”

“I guess so.”

“I know so,” said Kyle.

“How long have you been having those coffee dates with Lilly?” asked Brad.

“I don’t know. Maybe six weeks,” I said.

“And no DTR?” asked Kyle.

“No. Of course not,” I said.

Kyle and Brad exchanged a glance.

“Dude, it’s time,” said Kyle.

“For a DTR? No way! I need to give it a few more months!”

“That’s what you’ve been telling yourself your whole life.” His tone was friendly, but the truth struck deep.

“Yeah,” I said thoughtfully. “I guess you’re right. But even if I say yes to it now… when I’m with her I’ll choke.”

“Don’t worry about that,” said Kyle.

“Too late, already worried.”

“That’s because you haven’t heard about my boots yet.”

“Um, what?”

“I’ve got a pair of steel-toed boots under my bunk bed in my dorm,” explained Kyle. “The next time you see Lilly, if you don’t have a DTR, I am going to put on those boots and I am going to kick you as hard as I possibly can in your balls.”

“Excuse me?”

“You heard me.”

“You’re serious?”

“In your balls.”

“Steel?”

“Yes, it’s an iron alloy. I’m sure you’ve heard of it.”

“Are you joking?”

“Do I look like I’m joking?”

“He doesn’t look like he’s joking,” interjected Brad.

“Did I mention I was the starting forward of my high school soccer team?” asked Kyle. “I’ve got a mean left foot.”

“The next time I see her?”

“Or else.”

“Dude…” I said, incredulous.

“Steel. Your balls. Think about it.”

I sighed, surrendering. “Okay, you leave me no other choice. Next time I see her it is.”

“You do that, my boots stay under my bed.”

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“Thanks, I guess?”

“What else are friends for?”

I began by writing and memorizing a speech to give to Lilly, which I rehearsed endlessly to make it sound as spontaneous and organic as possible. The content of the speech? If you read the entry for the word “beautiful” in the thesaurus, you’ll have the basic idea.

I figured we needed a venue change for this date. A coffee shop wasn’t grand enough for the sweeping romanticism of my intentions and feelings. So I e-mailed Lilly and suggested that we go to the college’s boathouse, where we could borrow a canoe and paddle around Lake Matoaka, the serene (and romantic!) body of water tucked in the woods at the back of campus.

She agreed. I told Brad and Kyle: This is it. I am going for it. We are going to row out to the middle of the lake and confess our love for each other.

On the day of the big date, I knocked on her door and found a little powwow of Lilly and her friends on the rug in the center of her dorm room. I was too nervous about my upcoming speech, however, to pay any mind to the weirdness of the situation on the floor.

“Ready?” I asked.

“Yeppers,” she said. Indeed she was, decked out in a pair of Sperry Top-Siders and a coat with anchor-embossed gold buttons.

Her friend Sarah Martin, who was wearing too much makeup as usual, asked me, “What are you all doing?”

Not until later, when I would play back her question in my mind, would I hear how scripted it sounded, how well rehearsed. Not at all spontaneous or organic.

“Canoeing,” I said.

“Oh, can I come?” she asked.

Right on cue, Lilly and all her friends looked up at me as if their very lives were hanging on my reply.

“Um, sure,” I said, trying to hide my disappointment.

Again, I hadn’t noticed this was clearly a setup. I was too busy thinking about a steel-toed boot that would be dropping my voice two octaves if I didn’t find a way to have a DTR today, and how this addition of a third wheel on the date would make the conversation considerably more challenging. I mean, can you imagine a more uncomfortable social situation than having an uninvolved third party sitting in the middle of a canoe while the two other passengers hash out the details of what may turn out to be a completely one-sided romantic relationship?

But then, a miracle occurred. Lilly’s BFFL, Sadie, needed a ride to the bank. Lilly was the only one with a car. Lilly had to give Sadie a ride, drop Sadie off, and then drive back before we could go canoeing. I pounced.

“Can I come… keep you company?”

Lilly looked around at her group of friends. This was apparently a contingency they had not planned for. They had protected Lilly from being alone with me on top of a body of water in a romantic piece of floating fiberglass, yes, but not from this simple errand.

“Oh, um—the thing is…” Lilly struggled to find an excuse. But none came. “Sure, of course.”

After we dropped Sadie at the bank, I moved into the front seat of Lilly’s Volkswagen convertible. The roof was down. I had a window of approximately two minutes before we’d be back at her dorm to get Sarah and go to the lake. So I got right down to business.

“Lilly, there’s something I have to tell you,” I said, raising my voice over the wind.

She winced. Like she had been afraid this might happen. Undeterred, I spoke quickly, accelerating my words to be sure I finished my speech before we reached her dorm. As I spoke, I noticed that she was also accelerating—accelerating her car.

“Lilly, I think you’re incredibly beautiful, funny, smart, interesting, clever, pretty, stylish—”

“Josh, no,” she whimpered.

“Let me finish.” I had worked long and hard on these lines and I wasn’t about to end my performance prematurely. “Where was I?”

“Um, stylish?”

“Yeah—stylish, cool, fun, kind, charming, gorgeous…”

Based on her response so far, I knew this conversation was nose-diving, in complete free fall. MAYDAY MAYDAY. But Kyle and Brad had raised a good point: With Francesca and Evelyn, I could only look back and wonder, what if? I would only ever have a chance with Lilly if I took the plunge and told her I liked her.

“… cute, punctual, creative, intelligent, fashionable…”

And in my mind, that meant dropping this adjective bomb. I guess I believed that the more my speech sounded like an actual thesaurus entry, the more romantic it was. As if the number of adjectives a person uses to describe his affection is directly proportional to the chances it will be reciprocated.

“And that’s why I can’t stop thinking about you, all day, every single day.” Since she didn’t seem eager to turn her head and kiss me or anything, the speech ended in a whimper. “And I… just wanted you to know that.”

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“Oh, Josh,” she said. Her tone sounded like I had just told her I was facing a life-threatening illness.

I was silent.

“The fact is,” she said, “I have a crush on Sam Dayne.”

Sam Dayne? Sam… Dayne? That stung. I knew she had liked him during the fall semester, and they had dated a little, but I had heard through the rumor mill that he wasn’t much interested in her—he being both hilarious and a member of the football team, and therefore having his pick of the girls on campus—and she had since moved on. That last part, at least, turned out to not be true.

“Bummer,” I said.

By this time we were parking in front of her dorm. Sarah was standing outside, waiting for our boat outing.

“You still want to go canoeing?” Lilly asked.

I’m sure she expected me to say no. I mean, who in his right mind would want to keep hanging out after that? But partly out of a misguided need to demonstrate that her rejection had little effect on me, and partly because I knew how uncomfortable it would be for her to sit in a canoe with me now and I wanted her to suffer through every bit of awkwardness possible as punishment for not liking me back, I said yes, I would very much still like to go canoeing.

As it turned out, the only person I was punishing was myself. The canoes were two-person, so I ended up with a kayak while Lilly and Sarah shared the canoe. They were terrible paddlers, mostly spinning in circles and repeatedly colliding with the shoreline. So I just drifted behind in my kayak, always staying within earshot so as to delay the flood of gossip Lilly was no doubt eager to unleash. As long as they knew I was listening, my humiliation would remain a secret. You can’t talk about someone behind his back when he’s literally, you know, right behind your back—or your boat, as the case may be.

I plopped my tray of food down and laid my crutches on the floor underneath the table. Kyle and Brad were already seated, eating. Kyle had a pile of textbooks in front of him. They looked up at me, eyebrows raised.

I gave them one word. “Disastrous.”

They gave each other a look.

“What?” I asked.

They looked at the floor.

“What?” I demanded.

“That’s kind of what we expected,” confessed Kyle.

“You expected this?”

“Well, we knew she didn’t like you,” he said.

I held up my hand in a stop sign. “Hold up. You knew?”

“That’s an exaggeration,” said Brad. “I mean, well, we thought, based on how you described your conversations, that she had put you in the Friend Zone.”

I threw my hands in the air. These were supposed to be my friends! My two best friends! And they had betrayed me, sent me right into the lion’s den to get devoured.

“Are you kidding me?”

“Whoa, hear me out,” said Brad.

I folded my arms. “Fine. I’m listening.”

“We didn’t know for sure. I mean, maybe she did like you. We didn’t know. We just guessed that—”

“That she didn’t like me and you would screw me over?” I interrupted.

“Look, Josh,” said Kyle. “You’re what? Eighteen years old? And you’ve never told a girl you liked her. You’ve never had a DTR.”

That much was true. I stayed silent.

“You needed to try it. You needed to tell a girl how you felt about her. And if she doesn’t like you, so what?”

“So what?” I said. “So what? It’s horrible. I feel like she tore out my heart and threw it on the ground.”

Kyle held up a finger. “You feel like that, yes. And we’ve all been there and we all know how much it sucks. But here’s the thing: She didn’t literally tear out your heart. It’s actually still beating inside your chest.”

“Thanks for the helpful diagnosis, Dr. Premed,” I intoned sarcastically.

“No, what I mean is, you’re still alive. You got rejected. And you survived. Sure, it hurts. And it’s not something you’d want to do every day. But now you know you can live through it. And the next time a girl comes along, maybe it won’t be quite as terrifying to tell her you like her.”

I pursed my lips. I hated to admit it, but they were right. I had been rejected. And it sucked. But I had survived. And none of it would’ve happened in the first place if it weren’t for these friends. I was grateful. I would never admit it out loud, of course. But I did appreciate what they had done, how they had helped me. They had pushed me out of the nest. I didn’t fly, exactly. I basically fell straight down and smacked into the ground. But at least I was out of that nest.

Unfortunately, I was not quite finished humiliating myself with Lilly.