I’m not a betting man, though if I were to wager on the over/under of my life, I’d definitely bet the farm on “under.” In 2005, however, I did make a bet that would haunt me for nine years, right up until Thursday night last week when the circle was finally closed.

In those days, my friends Curtis, Nick, Cristina and I would occupy a reserved booth at The Paragon every Sunday night to hear Brandi Carlile play (this is when she was still playing the bar circuit before getting her first record contract). Rachel, our favorite waitress, had decided that we were also her favorite customers, and had us pick a table that she would reserve for us every week. We chose a corner booth in the back, where we’d listen to the music, write and read poetry, and catch up on the events of the week. The Paragon was our church.

It had been three years since I’d fouled up my last relationship with Aimee, and I was resolute that I wanted nothing to do with dating. Nothing at all. I was quite happy with the prospects of growing old alone, and romanticized the event of my eventual death where I was sure I’d be discovered a week after my demise, sitting in an easy chair with a notebook, a glass of whiskey and a cigarette butt still in my mouth. I’m not going to lie; this scenario still looks pretty good to me.

My position on love and relationships was a constant source of consternation for Cristina. Either it offended her philosophy constructed upon the premise that “love is life,” or she was trying to get with me. Either way, I wasn’t interested, but my relationship status became a topic of conversation every week for Cristina, and when I wasn’t moved, she decided to deploy a new tactic.

One Sunday night, Cristina pitched me her idea—a bet of sorts.

“I bet you can’t go on three dates,” she said.

“I don’t want to go on one date, let alone three.”

“If you can go on three dates, I’ll bleach my hair blonde,” she offered.

“If you can go on three dates, I’ll bleach my hair blonde,”

I paused to consider this. Cristina was a short, stout Hispanic girl with strict Goth/Fetish style rules that included anything black with buckles. She dyed her black hair blacker. She listened to Mudvayne. She took black and white photos of people dressed up like ghosts and demons in a project that she called “Afterlife.” We called her our little Mexican Hobbit. The thought of her as a platinum blonde was hilarious.

“It’s a lose-lose proposition, Cristina. I’d have to do something I don’t want to do in order to force you to do something you don’t want to do.”

Not only did the idea of going out on dates repulse me, I was concerned for the girls that would be unfortunate enough to go out with me. I’d have to lie, to feign interest, and what would happen if they liked me? How would I break it off if they wanted to keep seeing me? It was a moral conundrum. I’d be using these women under false pretenses, leading them to believe something that wasn’t true, and then potentially dashing their hopes. What an asshole thing to do.

Cristina sweetened the deal as she laid out the terms. The three dates could be with one woman or three different women if I wanted, so no one would have time to get too attached. The three dates had to occur within three months, however the clock wouldn’t start ticking until I’d gone on my first date, and there was no deadline for that. They had to be bona fide dates, meaning that I couldn’t count just meeting some girl in a bar. It required actually making plans and meeting somewhere. I didn’t have to provide physical evidence of the date; we could be on the honor system, but I had to report the details. If I completed my end of the deal, Cristina would bleach her hair blonde and wear it that way for two weeks. She couldn’t hide her hair under a hat or some other head covering, and she couldn’t just stay home for fourteen days—she still had to go to work and come out drinking with us. If I didn’t manage to log three dates, there didn’t seem to be any repercussions on my part.

It was an offer I couldn’t refuse. We shook hands.

I wasn’t in any hurry to get started. I dreaded the dates, and I feared the worst outcome considering the pretext. I all but forgot about the bet for a couple of months.

And then I saw the girl.

One night, my buddy Josh and I were playing pool in the back room at Charlie’s on Broadway. There were three pool tables, and the room was full of friendly drunks, so conversations spread around the room to include everyone like a happy contagion. The billiard room took on the characteristics of one big house party. And then I saw the girl.

There is perhaps nothing sexier than a girl playing pool. Even if you remove all of the obvious innuendo (sticks, balls, holes, nipples), the sight of a girl leaning over a pool table and handling a cue could probably have turned Saint Augustine into the Marquis de Sade. This particular girl, shooting with her friend at an adjacent table, however, had me seeing stars. A Hispanic girl with auburn hair, glowing brown skin, dark eyes, tall and svelte. She moved her lithe body with gracefulness like an alley cat, and rounded out the simile with an aloofness to match. I couldn’t take my eyes off of her.

A happy-go-lucky guy in the corner had started a game of guessing people’s ages and asking them to guess his. Like all of the rest of the conversations in the room that night, the game spread. I took the opportunity to strike up a conversation with the girl. We guessed at each other’s ages, and after I’d revealed mine (26), she refused to tell me hers.

“I don’t talk about myself,” she told me flatly. I thought she was kidding, but found out quickly that she wasn’t. I returned to my pool game a bit flummoxed.

After another drink, I summoned the courage to talk to her again, and I approached her while she was talking to her friend, maintaining as non-threatening a demeanor as possible.

“I’m Doug, by the way.”

“I’m Sway, and this is Rachel,” she said. Rachel shook my hand. Sway didn’t.

“So, come on, you’re really not going to tell me your age? That was the point of the whole game!”

“No.”

I tried to make conversation, but Sway didn’t engage. She didn’t laugh at my jokes, she didn’t ask questions or offer her own insights into whatever trivial topic I pursued, and she definitely didn’t tell me anything about herself. But she hadn’t given me any obvious signs that she wanted me to leave her alone either, so I didn’t know how to interpret her. Deciding that she was polite but uninterested, I gave up and returned to my own pool game with Josh.

Josh, however, decided that he’d had enough to drink, and after another game, decided he was ready to go home. We started to gather our things and asked a server to close out our tabs at the bar. Sway approached me.

“What are you guys up to now?” she asked.

“Well, my buddy’s drunk, so he needs to drive home,” I joked. “I guess I’m getting out of here, too.”

“My friends and I are getting a table,” she said, motioning toward the dining area in the bar. “You should come join us.”

“What, are you going to talk to me?” I asked with a laugh.

“Come sit down with us,” she replied, not technically answering my question.

That’s when I remembered the bet. As stilted as our interaction had been, she was inviting me to spend more time with her. This could be an opportunity to set up the first of my three dates. Even better, there didn’t seem to be much risk of this girl getting attached to anyone, let alone me. It could be a safe way to tick the first box on my list.

I saw Josh off, and then sat down next to Sway in a chair pulled up to the end of a booth occupied by her friends. I’d met Rachel already, but I wasn’t introduced to the other two people sitting there. Sway and I made small talk, and by “small talk,” I mean that I talked to her while she said next to nothing. I tossed up funny anecdotes (she didn’t laugh), offered my perspective on observations (she didn’t reciprocate), asked her questions (she didn’t answer), and tried any other method of verbal peacocking that I could think of. Why had she asked me to join her and her friends if she wasn’t going to engage in a conversation? I just couldn’t figure it out. I decided to simply say goodbye.

“I’m going to take off. Will I run into you here again? Do you ‘come here often?'” I made air quotes and laughed at my clever use of the cliché.

“No, I don’t,” she said flatly.

“OK, well, it was nice meeting you, Sway.”

“We should get together again,” she said, surprising the shit out of me.

“OK, you want to give me your phone number?” I suggested, getting out my pocket notebook and a pen.

“No, but you can give me yours.”

“Are you going to call me?”

“I will if you want me to.”

When a pretty girl asks for your phone number, you just give it to her.

I couldn’t untangle the mixed signals, but when a pretty girl asks for your phone number, you just give it to her. I wrote my name and number on a piece of notebook paper, and handed it to her. I said goodnight, and left.

The next night, while settling onto my couch to read after coming home from work, I noticed I’d missed a call from a number I didn’t recognize, and there was a voicemail. I listened.

“Hi, Doug. This is Linda. We met last night playing pool. I had fun, and we should get together again, so, uh, call me back.”

Who the fuck was Linda? I remembered talking to Sway, but no one else. Was Linda Sway’s friend? I thought that girl’s name was Rachel, but I might be wrong. Did Sway give my number to Linda? Was I so drunk last night that I totally forgot talking to someone else? Did I hear the voicemail wrong?

I listened again. She clearly said Linda. What the hell?

I called the number back, and I got an automated voicemail greeting. “The person you are trying to reach is unavailable. Please leave a message after the tone. For more delivery options, press 1.”

“Hi, uh, Linda. This is Doug. I got your message, and…yeah. Call me back.”

I set my phone down on the coffee table and went to the kitchen to make dinner. I kept racking my brain, trying to recall the events from the previous night. I remembered the details clearly, right up until I’d gotten into bed. There were no fuzzy memories, so it didn’t seem likely that I’d forgotten entire people and conversations, but it was still possible that I’d had a brown-out at some point, even though I never felt that intoxicated. I searched my memory for anything I might have forgotten, but couldn’t find it.

I took my dinner into the living room and sat down on the couch with the latest copy of The New Yorker. I picked up my phone and noticed I’d missed another call. There was another voicemail.

“Hi, Doug. This is Linda again. It looks like we’re playing phone tag, and you’re ‘it.’ Call me back.”

I called the number.

“Hello?” Linda answered.

“Hi, this is Doug,” I said cheerfully, hiding my confusion.

I thought the sound of her voice would help solve the mystery, but it didn’t. I was too embarrassed to ask for clarification. Seriously, what could I say without sounding like a dick? Which one were you? Or, Remind me who you are. Or, I don’t remember meeting anyone named Linda. The conversation was short, but somehow we made plans to meet at Julia’s at 7:00 the following night. I hung up the phone still not knowing who I’d see when I showed up for the date. Would I even recognize this girl? If not, how would I identify her in the bar? This girl had clearly met me before, so I couldn’t exactly ask her to wear a white rose in her lapel, now could I?

I decided that I had to be the first one to arrive so that she would have to find me. If a girl walked up to my table, sat down and called me by my name, I’d know that she was the one. On the night of our date, I showed up half an hour before we were supposed to meet. The host seated me and I sat facing the door, scanning faces over the rim of my glass of whiskey.

At 7:00 and on my second Jack Daniels, no one had approached me. I wondered if she’d also arrived early and gotten her own table expecting me to find her. I looked at every table, but I didn’t see any women sitting alone. Maybe she’d come and gone. Maybe she’d stood me up. Maybe this was a huge elaborate hoax!

Then Sway walked in. She saw me from the door, and came straight to my table smiling.

“Hi, how are you?” I greeted her.

“I’m good. Am I late?” she said in the friendliest tone I’d seen yet.

“No, you’re right on time,” I said, smiling.

I was relieved that I wasn’t meeting someone I didn’t remember, but I started to doubt that I’d heard her name correctly to begin with. I’d listened to the voicemail several times, and it clearly said Linda. So, why had I thought her name was Sway? Did I just hear it wrong? “Sway” and “Linda” don’t sound much alike, though, so how could I have gotten that confused? I decided to ignore it for the time being. They say that people like to hear their own name, and you’re supposed to use a person’s name when talking to them if you want to really connect, but I avoided using her name as if she were Rumpelstiltskin.

Completely unfamiliar with the game of dating, I didn’t know what to do. To this day, I don’t know how to flirt, and at the time, I wasn’t trying to pursue anything beyond getting my first date out of the way to win my bet with Cristina. Linda and I chatted for a couple of hours over drinks. She was more communicative than before, she had a nice laugh and she allowed herself to be more vulnerable than the toughie she’d presented the night before. When she smiled, it was almost bashful, as if she was slightly embarrassed to be smiling at all. It was endearing. Before I knew it, I was having a really nice time.

As the date was coming to a close, I had to find out about the name situation.

“Can I ask you a question?” I asked.

“Sure.”

“When we met last night at Charlie’s, I could have sworn that you told me your name was ‘Sway.'”

“That’s right.”

“But it’s not. It’s Linda?”

“Yeah, ‘Sway’ is just the name I use in bars.”

“You give a fake name in bars? What for?”

“Because you never know what kind of creeps you’re going to meet.”

It turns out that this is fairly common. I’ve heard from several girls since then that they use fake names when hanging out in bars. I don’t get it. It’s not like offering your first name will allow some creep to find you online, search for your address or telephone number, and begin stalking you. I can’t imagine a scenario where offering a first name would open the door to a threatening situation. But, I’m just a guy. In any case, the mystery was solved, and I was relieved that my sanity was still moderately intact.

As we left the bar, I didn’t know how to end the date. So, in my patented move, I shook her hand. Yes, I actually shook her hand. No hugs, no kisses, just a good firm American handshake. And then I surprised myself.

“I had a really nice time tonight. We should do this again,” I told her. Did I just ask her out again? What the hell, dude!

“That would be great.” Holy shit, she wants to go out with me again!

“Cool, I’ll call you soon,” I said casually, while not quite succeeding at hiding a dopey grin.

I was curious to see where it might go.

We went out on a second date, and then a third within a week. I called Cristina and told her I’d fulfilled my end of the bet. By the following night, Cristina sent me a picture of her new blonde hair. It was every bit as hilarious as I’d hoped it would be, and for the next two Sundays, I relished the way she was so self-conscious during our weekly meet-ups at The Paragon. But now there was something bigger than the bet at play here. I actually liked Linda. I was having fun hanging out with her, and I was curious to see where it might go. This constituted something of an identity crisis for me, considering how vocally adamant I’d been about never dating anyone again ever. I also knew that our first few dates had been predicated by a lie.

I didn’t want to be the asshole that I’d been in my last relationship and ruin everything.

Still, I kept seeing her. I told her I wanted to take things slow. I didn’t sleep with her right away. We spent time getting to know each other. I learned that she’d had some terrible experiences with guys in the past (though she never told me the details about the nature of these experiences), which was why she was so guarded and distrustful. Fancying myself the Best Guy In The World, I set out to build trust with her. I wanted her to know that I wasn’t going to take advantage of her, and that I wasn’t spending time with her just to get laid. This last bit was a little frustrating for her, because as she said, she was a “physically passionate person.” But, I was hesitant to let things move along very quickly since I didn’t want to be the asshole that I’d been in my last relationship and ruin everything. However, I couldn’t deny that I really liked her.

I confided in Cristina that her sinister plan had worked. Because of her meddling, I’d found myself in a relationship with a girl that I really cared about. Naturally, Cristina wanted to meet this girl who’d managed to get me to give up my life of solitude, so we all met at Charlie’s one evening to play pool. Cristina acted like a different person that night. She was unfriendly, made sardonic jokes and disparaging remarks, and kept disappearing for a few minutes at a time. Eventually, a stranger found her in the bathroom having a cocaine-induced breakdown. I’d never heard of Cristina using any drugs but weed. Linda went into the restroom and took care of her, but Cristina wasn’t done making a mess of things.

“I’m going home,” Linda barked at me.

“What? Already?”

“We need to talk,” she told me angrily and dragged me into the alley behind the bar. “Are you just fucking with me or what?” she demanded.

“What are you talking about?!

“Your friend Cristina just told me that I needed to be careful about you,” she said accusingly.

I calmed Linda down enough for her to tell me the story. Cristina had thanked her for taking care of her and apologized for nearly overdosing on coke in the bathroom and making a scene. Then she gave Linda some friendly advice.

“Doug’s great,” Cristina told her, “he’s just greeeaaaaaat. Just be careful.”

Linda asked her what she meant.

“Oh, hey, he’s really great. I’m just saying you should guard your heart.”

Linda again asked her to clarify.

“Never mind. It’s nothing. I’m just saying.”

This was not the kind of thing you say to a girl with trust issues, and Cristina knew it. I said everything I could think of to assure Linda that I wasn’t going to hurt her, but she was adamant about going home alone to think it over.

“I’m going home. Alone. Don’t follow me. Don’t call me. You go deal with your friend. I’m done here.” I watched her walk away.

When I went back inside, Cristina asked if she could stay at my place, because she was in no condition to go home. I consented, but I spent most of the walk to my apartment yelling at her. As we passed through an empty intersection in my neighborhood, she had a meltdown in the middle of the street, dropping to her knees on the asphalt and crying under a streetlight in true Gothic melodrama, forcing a turning of tables where I needed to be the sensitive one and console her. It was a genius move on her part.

The next day, Linda and I talked again. She had come to the conclusion that Cristina had unexpressed feelings for me and was deliberately trying to ruin things for us. I agreed that that sounded perfectly plausible, and I offered my own similar theory that Cristina had made a play that ensured she’d been the one to go home with me—even in platonic terms—rather than Linda, establishing her place on some weird, misguided hierarchy. Linda decided to trust me, and I resolved to do everything in my power to demonstrate that she could.

Linda and I spent a lot of time together. She began to trust me, and opened up a little more each day. In turn, I began to let my guard down. Soon, I couldn’t avoid the fact that Linda was my girlfriend. We started sleeping together. She let me read children’s books to her aloud including The Little PrinceLafcadio, The Lion Who Shot Back; and The Missing Piece. We started having brunch on weekends. We instituted “Naked Sunday,” where we’d lie in bed naked all afternoon and read together. She brought over a title from Sir Arthur Conan Doyle that her father had given to her before he died, and we took turns reading chapters to each other as we basked in the sunlight filtering through the blinds.

Life was good.

How could I be trustworthy if I was still keeping a secret from her?

It was still nagging on me, though, that I hadn’t told her about the initial bet. How could I be trustworthy if I was still keeping a secret from her? So, one night, sitting on my couch together, I told her. I delivered the story in a funny, you’re-not-going-to-believe-this-but kind of way. I laughed disarmingly with a “isn’t it crazy how well things turned out?” She was not amused. In fact, she was angry. Really angry. She packed up her things and left without so much as a goodbye.

For a solid week, she wouldn’t answer the phone or return my calls. I felt terrible. I felt guilty. I felt like Worst Guy In The World. I wasn’t sure what to do, so I decided to consult a fortune teller.

Kay was a woman who worked for me. She was a great employee, a barrel of laughs, genuinely friendly, and also happened to claim that she was a seer. She wasn’t weird or exotic like you’d imagine a fortune-teller to be. You’d never pick her out of a crowd except for her winning personality and lively nature.

“I have a question for you,” I told her one evening at work outside my office.

“Sure.”

“You say you can see things. You know I don’t put much stock in that stuff, but let’s see what you can see.”

“OK, what’s the deal?”

“I’ve been seeing this girl—”

“Mmm-hmm…”

“I want to know if she’s good news or bad news.”

“What’s going on with her?”

“Oh, no, I’m not giving you any more information than that. If you can really see things, then you won’t need any clues. Just tell me, is she good news or bad news?”

“OK, give me your hand.”

Kay took my hand and ran her fingers along the lines. She stared at it. She turned it over and back again.

“Would you mind if I touched your chest?” she asked, “I’m not getting anything from your hand.”

“Sure, no problem.”

Kay put her hand on my chest and closed her eyes.

“Holy crap,” she said, “I’ve never seen an aura this color before.”

“What’s it like? What does that mean?”

“It’s not a typical color of the rainbow. It’s like all colors rolled into one, but it’s not white. I don’t know how to describe it; I’ve never seen it before.”

“Is that a good thing or a bad thing?”

“It’s definitely a good thing, but it doesn’t relate to your question. I just thought I’d share that. Now, about this girl…”

Kay fell silent for a minute, her hand firmly on my heart.

“Is she blonde?”

“A swing and a miss.”

“She’s not blonde?”

“No.”

“Who’s the blonde girl?”

“I don’t know any blonde girls.”

“Well, if you don’t know any blondes now, you will. You’ll meet a blonde girl, and I like her. I can’t say whether or not you’ll date, but she will have a big impact on your life for the better. Keep your eyes open for her.”

“OK,” I said, “but what about the girl I’m dating now?

“Hmmm…she’s not at your level,” Kay said. “She hasn’t developed to the same place you have, cosmically speaking. That’s not a good thing or a bad thing. It’s nothing against her. You and she are just in different places. Nothing’s set in stone. There is still free will, and if you pursue things with this girl, it could be very, very rewarding, but it will also be a lot of work.”

“You’re getting that from the mere fact that I asked about her, aren’t you?”

“No, I just see a lot of strife,” she said. “There’s not one right person for everybody, and you could make it work with this girl, but it’ll take a lot of energy to maintain. You’ll have to put in a lot of effort, and it won’t come easy, but it could still be really rewarding. Just hard.”

“OK, thanks,” I told her and started to walk away.

“Wait, you’re not going to tell me about her?”

“Nope!” I laughed and walked on.

I needed a plan to patch things up.

The next day, I decided that I owed it to myself and to Linda to keep trying and to see where things could lead, so I needed a plan to patch things up. I remembered how much she’d loved Shel Silverstein’s book The Missing Piece when I’d read it to her. So, I walked down to a bookstore in the bowels of the Pike Place Market, conveniently located just two doors down from the import store where Linda worked. I bought a copy of The Missing Piece Meets the Big O. In this sequel, the Missing Piece (a wedge shape like a piece of pie) is looking for the larger, incomplete circle (missing a wedge shape) with which to unite and become whole. However, the Missing Piece meets a whole circle, who doesn’t need a missing piece, and who teaches it to roll on its own (awkwardly at first) until its sharp edges are reshaped and it becomes a whole circle itself. Then, they roll on side by side as equals, relishing the companionship rather than codependency.

With the book, I bought a round greeting card. In it, I wrote:

You can roll on your own
And so can I
But perhaps we can roll
Together for a while.

I put the card in the book, and asked the shop owner to hand-deliver the book to Linda. I explained that I’d done something terrible, and that I was trying to get my girlfriend back. Whether it was just to make a sale, or if the guy had genuine sympathy for me, I’ll never know; but he agreed to deliver it.

That night, I went to a Seattle Sonics game at the Key Arena with my boss, who’d gotten tickets to a suite from the accounts manager of the newspaper in which we advertised. We were given free food, beer, and a view of the court unsurpassed by any seat in the house. It should have been a great time, but I spent it worrying about Linda.

In the third quarter, I got a text from Rachel, Linda’s friend.

“Call me.”

I excused myself, found a patio outside that was a designated smoking area, and called Rachel.

“Doug, have you heard from Linda?!”

“No, I’ve been trying to get a hold of her all week, but she’s not answering my calls.”

“She’s moving back to Mexico!

What?!

“She’s been upset all week, and she just sent me a text saying she was moving back to Mexico tomorrow to live with her grandmother, because it hurts too much to be in Seattle.”

“Holy shit! I’ll call you back!” I hung up the phone.

I started calling Linda repeatedly. I sent text messages. I called. I sent texts. I called. I got no response.

I called Rachel back, but she didn’t answer. I spent the third and fourth quarters of the basketball game pacing around on the patio in a panic, trying to get in touch with either one of them and completely ignoring my boss, but neither of them would answer the phone or reply to texts. Finally, having missed the game, I got a text from Linda.

“April Fool’s. I’ll call you tomorrow.”

It was April 1st. She’d gotten me good. It was payback, and payback’s a bitch. When I returned to the suite, my boss was putting on his jacket, getting ready to leave.

“Hey, there you are” he said “Is everything OK?”

“I think so, now,” I told him.

When Linda and I talked, she told me how much she’d loved the book and the card I’d had delivered to her. She told me that what I’d done was stupid and that she wished I hadn’t told her, but she acknowledged that my intentions were good, and agreed to look past the whole thing and keep seeing me. But, she thought I should have to pay, so she’d devised the April Fool’s plan with Rachel to even the score. I deserved that.

We managed to get our relationship back on track, and one Saturday afternoon, I was sitting at my desk in my apartment, writing poetry, absorbed in thought about my life that now included Linda. I still wasn’t sure I was comfortable with the idea of love (though that didn’t stop me from doing everything I could to make our relationship a good one), but I could feel myself warming up to it, and that in itself felt monumentally significant. I decided to lay this all out in a letter to her.

It was a twenty-six-going-on-thirteen-year-old masterpiece.

I got out some brown paper, and began writing my missive. I included prose. I included poetry. I included demonstrative drawings and illustrations. I sewed book-binding thread through the heart of a rough, charcoal self-portrait and left the ends of the string dangling like shoelaces to represent how I was opening up emotionally. I drew mandalas. I tore the edges of the paper and sewed a border in thread. I poured out my thoughts in every medium, aiming at both full transparency and appreciation for the impact she was having on me. I made an envelope, sewn together with more thread, and drew more illustrations on the back side of it. I sent it through the mail, even though she lived just a couple of blocks from me—the letter as a multi-media piece of art wouldn’t be complete without a postage stamp and the official markings applied by the post office. It was a twenty-six-going-on-thirteen-year-old masterpiece.

Two days later, I got a call from Linda, and she wanted to talk about the letter. We got together, and she explained to me that it was kind of weird. People just don’t do things like that. On the other hand, she’d never read anything like it and didn’t quite know what to say. She was really moved, and it meant a lot to her. She didn’t know how to react to something like this. I felt dumb and proud at the same time. I told her that she didn’t have to say anything—I was just trying to be honest and transparent. She smiled.

Despite the fact that I’d bumbled my way into and through this relationship, things went on with only minor hitches that I handled with finesse. Until I didn’t.

I was set to go to Eugene, Oregon for a week to help open a new store for my company. In addition to being a Store Manager, I was a Regional Trainer, so among other things, I’d go to all the new store openings and spend time preparing the staff until opening day. The night before I left, Linda stayed at my place.

As we laid in bed together, holding each other in the dark as we were going to sleep, I opened my eyes and noticed that she was staring at me intently with an unidentifiable expression on her face. I could tell her mind was working overtime.

“What’s on your mind?” I asked her.

“What? Nothing.”

“Why are you looking at me like that?”

“Nothing. Don’t worry about it.”

“I can tell you’re thinking about something. I can see it on your face.”

“Never mind!

“C’mon, you can tell me. What’s going on?”

“I’m not sure you’re ready to hear it.”

“You can tell me anything,” I assured her. (Stupid! Stupid! Stupid!)

“I think I’m in love with you.”

If someone doesn’t want to tell you something, it is never, ever a good idea to tease it out of them.

Oh-shit-oh-shit-oh-shit! If I had only one piece of advice to give, it would be this: if someone doesn’t want to tell you something, it is never, ever a good idea to tease it out of them. Whatever the reason for their hesitancy, there’s still a goddamn reason.

I didn’t know what to say or do.

“I’m so glad you felt comfortable enough with me to be able to tell me that,” I said while giving her a pat-hug. Definitely not the reaction she was hoping for. I didn’t want to alarm her, but I was in full freak-out mode. I liked Linda and I cared about her, and that was already a giant step for me, but in love? No. You don’t take an agoraphobic person to Disneyland the first time he steps foot outside of his home in years. We both fell silent and tried to pretend this whole little exchange never happened. I went to sleep.

Ralph Waldo Emerson wrote that,

The voyage of the best ship is a zigzag line of a hundred tacks. See the line from a sufficient distance, and it straightens itself to the average tendency. Your genuine action will explain itself, and will explain your other genuine actions.

There are, however, many moments that aren’t genuine, and these can alter the course of your life completely. We are about to take a left turn.

I left for Eugene the next day. Store openings were like a reunion in my company. They’d send the best of the best from around the company to launch the store, and these people all had a philosophy like mine: work hard, play hard. We’d work our asses off from 6 a.m. to 6 p.m., and then grab a bite, hit the bars and drink ourselves into oblivion until they closed at 2 a.m. Then we’d do it all again the next day.

When I stepped into the store, I was greeted loudly by a bunch of people I’d opened stores with before. Every one of them shook my hand, slapped me on the back, and said, “Where are we drinking tonight?” as if I was naturally the one with a plan. I had a plan.

“I really want to go to this little dive I saw on the way in called Lucky Larry’s,” I told each of them.

That week, within large groups and small, I spent most of my time hanging out with a couple of managers from Washington. She, he and I became kind of a clique, organizing ourselves to arrive and leave together when meeting up with everyone else. One night after returning to the hotel after all the bars had closed, we sneaked into the hotel’s pool area after hours and soaked in the hot tub in our underwear. Though she kept her camisole on to retain a modicum of modesty in an ostensibly naughty situation, I couldn’t stop glancing at her out of the corner of my eye and hoping that I wouldn’t get wood.

One night, late in the week, she and I found ourselves alone at Lucky Larry’s after everyone else had decided they needed at least one night of sleep and headed back to the hotel. Not only was she talented and a hard worker—the whole reason she’d been chosen to come to Eugene—but she was beautiful. She was sexy. She was engaging, and a little flirty.

I told her about my girlfriend, and admitted I was in a pickle. She told me about her shitty marriage. The more drinks I had, the more I felt like I had a connection with this girl. She seemed to be flirting with me, and I kind of liked her. She had invited me to have drinks in her hotel room with her the night before, and I’d run away scared as if she was inviting me to an orgy. But on this night, I thought we were bonding beyond the casual friendships I had with all the others I’d been working with.

“What’s on your mind?” she asked me.

“What? Nothing.”

“You have a look on your face like you’re thinking really hard about something.”

“Nah, it’s really nothing,” I told her, awkwardly taking another sip of whiskey to avoid talking.

“Seriously, what is it?”

“Well, it’s just that, you know, we’ve been spending a lot of time together this week, and…”

“Yes?” She put her hand on my knee to let me know it was OK to proceed with what she already knew I was going to say.

“Well, I have to admit that I’m really attracted to you. I know it’s all kinds of wrong, but it’s true.”

She giggled, pleased as punch to hear it. She squeezed my knee again to affirm that everything was A-OK.

We closed out our tabs and headed back to our hotel. As we passed by her room, she asked me if I wanted to come in for one last drink. I agreed, and we stopped at her door.

“I swear, when I asked you if you wanted to stop by last night, you ran away like I’d scared the shit out of you,” she told me as she unlocked the door.

“I just thought it would be inappropriate for me to hang out with you in your room,” I explained.

“But you don’t think so now?”

“Oh, I definitely think so now, but I don’t care.”

We went inside, she poured some vodka into hotel water glasses and gave me one of them. I stood by the window, staring out.

“See, I told you my room was overlooking the porn store!” she laughed. It was true. Right below her window, there was a sex shop. “We should go down there and check it out,” she suggested.

It seemed so risqué, a natural extension of my admission of attraction and agreeing to drink with her in her room. I didn’t want to think about where this was leading. I’d now gone into complete devil-may-care mode.

The porn store was still open, and we walked around looking at toys, movie titles, etc. She’d hold up a DVD and ask if I thought the cover was hot. That’s one of the more awkward things a girl can ask you. If you say yes, then you’re saying you love the fake, augmented and unrealistic big-titted bimbos. If you say no, well then you’re either gay or have serious sexual inhibitions. She loved to see me squirm at the question, and kept it up.

The clerk—a skinny dude with blue hair, a torn fishnet muscle shirt and leather pants—asked us if we needed help.

“Oh, we’re just in town on business, and we’re staying in the hotel next door,” she said. “We just thought we come check out your store.”

“Riiiiiight,” the clerk said with a knowing smirk and a wink.

“I’ve seen enough,” I whispered to her, “Let’s get out of here.”

We went back to her room and sat on the small couch, the very nature of which forced us to sit very close together. We sipped on our vodka while she teased me about my discomfort in the sex shop. Everything she said and did was translated in my head as, “Relax, you’re not at home, it’s OK, do whatever you want to do.” She had flirted with me, encouraged me, practically coerced me into this situation, right? She wanted this. So, I leaned in and kissed her.

I kept kissing her like a puppy trying to hump an area rug.

She didn’t exactly push me away, but she also wasn’t at all participatory. Her lips remained stiff, closed and cold. When I tried to pull her close, she remained pressed firmly to her end of the couch. If she had been trying to seduce me until this moment, then she definitely wasn’t rolling out the welcome mat for me now; but I kept kissing her like a puppy trying to hump an area rug. I was going for the full make-out while wondering how such a sexy girl could be such a bad kisser. When I pulled away, she looked a little surprised and disconcerted by the whole episode. I began to realize just what a shitty thing I’d just done.

“We should talk,” I told her, because I tend to think everything needs to be talked about, “before this goes any further.”

“What do you need to talk about?” she asked, “I’m not going to sleep with you.”

“Well, that’s exactly…I mean, I don’t want…I was going to say…” I stammered, “I gotta go!”

She tried to put me at ease and put my mistake behind us, but I got up and raced out of the room and back to my own. I’d just done the worst thing of my life.

I was scheduled to travel back to Seattle the next day, and I came home not knowing what I was going to do about Linda. I knew I had to come clean about what had happened, but what was I going to say? How would she react?

I called her up and we made plans to have dinner. We met up at taquiera on Broadway, and over food, I filled her in on my week. I told her about the store, the team with whom I’d worked, workplace anecdotes and a bunch of other things she couldn’t have been interested in. As we finished dinner, I told her I didn’t want her to come back to my place, because I was so tired from my week. We walked together in the direction of our respective apartments, and I began to tell her about all the bars and drinking we’d done in Eugene.

“It was funny, one night after we’d closed down the bar, this guy and this girl and I sneaked into our hotel’s pool area after it was closed, and went into the hot tub in our underwear.”

“You went hot-tubbing naked with some girl?” Linda didn’t look amused. At all. She looked angry.

“It wasn’t just a girl, it was with a guy, too. It was his idea, actually,” I defended myself, “and we weren’t naked. It was totally innocent. I was in my boxers, and she left her camisole on. He was wearing briefs, though, and nobody wanted to see that,” I laughed.

“Why are you telling me this?” Linda asked.

“What?”

“Why would you tell me something like this?”

“Well, because it happened. Because it’s the truth.”

“Sometimes people’s feelings are more important than the truth,” she said flatly.

Sometimes people’s feelings are more important than the truth.

Those words would haunt me for years. Sometimes people’s feelings are more important than the truth. As an idealist, I’ve never considered anything to be more important than the truth. I’ve spent my life pursuing truth, gathering data, maintaining a firm grip on reality. I can’t imagine anyone actively avoiding information, but then again, I seem to hurt a lot of feelings.

Clearly, she wouldn’t want to know about the kiss.

As we came to her street, I said goodnight and continued to walk home with a heavy conscience. I’d done something really terrible, and now I couldn’t even come clean about it, because telling the truth would be worse for Linda than the secret. But, doesn’t keeping secrets make me even less trustworthy? In the long run, wouldn’t she rather know that if I ever fucked up, I’d be honest about it?

The next day, Linda came over to my place. I paced around, and told her we needed to talk.

I told her we needed to break up. She was obviously confused, but I couldn’t explain why since I didn’t think she wanted to hear it. Sometimes people’s feelings are more important than the truth. I told her that if we stayed together, she was going to get hurt. I told her I cared too much for her to let that happen. When she protested, I told her that it was inevitable that things would end terribly later, and that I wanted to protect her from that. I told her that I would hurt her badly, and that it was better to end things now before that happened—that the pain she was feeling now was better than the pain she was bound to feel later if we let things continue. She told me that I was being stupid, but I couldn’t be swayed. It was over.

She left crying. She left bewildered. She left angry.

I wanted to be purified by fire.

I was torn up inside. I felt that I’d done the right thing, but I didn’t get any absolution for my sins. That terrible kiss was still weighing on me, and I hadn’t come clean. I didn’t want forgiveness, but I did want her to know what an awful person I was. I wanted my own scarlet letter. I wanted to be locked in the stocks in some public square to be scorned by all of humanity. I wanted her to hate me, not merely to be confused by my ostensibly irrational decision to break up. I wanted to be purified by fire.

So, I wrote her another letter. This one was short. I still didn’t tell her about the kiss (I was trying to honor her wish not to know these things), but I did confess that I’d already done something terrible, something hurtful. I told her that I wasn’t actually protecting her from some future transgression, but that I was reacting to my actions in the recent past that were unworthy of her. I danced around the reason for the breakup without penning the actual words. I put the letter in the mail.

Two days later, Linda called me, and wanted to talk. We met in a little park across the street from my apartment building. She pulled the letter out of her handbag, set it on the bench next to me, and said, “Did you think I wasn’t going to ask?”

“Do you really want to know?” I asked. “You didn’t want to hear about the hot tub, and that was innocent.”

“What happened?”

I told her about the kiss.

“Did you sleep with her?”

“No, of course not.”

“You just kissed?”

“Yes,” I told her, “but it’s still cheating.”

“Are you going to see her again?”

“No, of course not. She’s married for fucksake.”

“I want to know why you haven’t apologized,” she said, “I want to know why you’re not sitting there begging for my forgiveness.”

“I can’t ask for your forgiveness,” I told her, “because I don’t deserve to be forgiven. What I did is unforgivable. I’ve spent my entire life trying to be a good man, to live with integrity, to live beyond reproach. I’ve spent my life trying to be trustworthy, to be good to people around me, to have a positive impact on the world. I’ve spent my life dedicated to doing the right thing. And in one night, I proved that it was all for naught.”

“It was a shitty thing to do,” she agreed, “but it’s not as bad as sleeping with her. It’s not something we can’t work through.”

Linda was trying to give me an opportunity to take her back. She was giving me the chance to apologize so she could forgive me, and so we could keep moving forward in our relationship.

“Even if you forgave me, you’d never be able to forget.”

“Don’t you see? It is something we can’t work through!” I told her. “I’ve destroyed all of my credibility! I’ve proven that I can’t be trusted. I’ve proven to you and to myself that I’m a shitty person. Even if you forgave me—and you shouldn’t—you’d never be able to forget. Every time I took a trip for work, you’d wonder if I was cheating on you. Every time I hung out with a female friend, you’d wonder if something else was going on. You may be able to forgive me, but you’ll never be able to trust me again. There will always be that nagging doubt in your mind, that lingering suspicion, that worry that at any moment I’ll step over the line into infidelity. No matter how much I tried to make it up to you, you will never be able to forget what I’ve done. It isn’t just about what I did on one particular night; it’s that I’ve demonstrated that I’m the kind of person that would do that kind of thing. So, no, I won’t ask your forgiveness, because I can’t even forgive myself.”

“I thought you were the one,” she said quietly.

“Turns out, I’m just another in a line of assholes that have treated you badly,” I said.

She simply stood up and walked away. I wouldn’t see her or talk to her again for nine years.

Even if I could have forgotten about this whole episode, I still had a reminder that would make me think of her every once in a while. Tucked away in one of my nightstand drawers was that book she’d brought over for us to read together on Sunday afternoons. The book her father had given her before he passed away. Months went by, and then years. I didn’t know how to contact her anymore, but I knew I had to hold on to that book until I could find a way to return it to her. I left it in the nightstand drawer that I don’t use, because I knew there was a good chance it would get lost if I added it to my own book shelves. Every few months over the past nine years, I’d open that drawer when I was looking for something I’d lost, or when I was dusting, or when I’d forget what was in it. I’d see the book, and be reminded of the past, of my failure, and of my commitment to return that book to her. Hidden away in that drawer was my own scarlet letter.

Last week, on Thursday night, I was shooting pool with my buddy Curtis at The Hillside Bar. I looked up, and sitting there at the bar was a familiar face that made my stomach turn.

Linda looked exactly as she had nine years ago. She didn’t even appear to have aged by a decade or a day. I felt a little sick. I knew I had to talk to her, but I walked past her several times without uttering a sound. She was with a guy, watching the Seahawks game on the overhead television. I didn’t know how to approach her.

Eventually, the guy went outside to smoke, and I knew I couldn’t wait any longer. I walked right up to her.

“Linda?”

She looked at me with a perfect poker face.

“It’s Doug,” I reminded her, in case she didn’t recognize me. I held out my hand for a handshake. She didn’t shake my hand. She didn’t say a word.

“Uh…it’s been a long time.” Silence. “I hope you’ve been well.” Silence.

“Listen,” I continued, “I still have a book of yours, and I’d like to get it back to you somehow.”

“What is it?” she asked. Her voice sounded the same, too.

“I don’t remember the title, but we were reading it together way back when, and you said it was special to you.”

“But you don’t remember what it is?”

“No, but you’d said that it was a book that your dad had given to you before he passed away. I’ve kept it all this time, thinking I needed to return it, but I haven’t known how.”

“You know what…” she paused, conflicted, “just keep it.” She sounded like she was already exhausted from this conversation, and just wanted me to go away.

“Again, you’d said it was really special to you. I can mail it to you if you’d like, or we can find some other way for me to get it to you.”

She considered this. “Do you still live on the Hill?” she asked.

“I still live in the same apartment,” I told her.

“Why don’t you email me the title,” she said, still trying to cut the conversation short.

“Listen, I’m really sorry to have bothered you,” I said, holding up my hands to show I meant no harm. At that moment, the guy she was with came back inside and saw me. He rushed up to us.

“Hey, is everything all right here?” He was glaring at me like I was harassing his girlfriend. He looked ready to fight me.

“It’s fine. We used to know each other a long time ago,” I reassured him. Linda gave him a slight nod to let him know she wasn’t in danger.

“OK, then,” he said like it was a warning, and he sat down.

“I’ll email you the title if you want. Just give me your email address.”

“Why don’t you give me your email address, and maybe I’ll email you,” she replied. I asked the bartender for a pen, and wrote it down on a napkin.

“There you go,” I told her, “Take care.” I walked away.

A few minutes later, Curtis had to leave, and I followed shortly after. It occurred to me that I was just a few blocks from home—a few blocks from Linda’s book. I walked home, collected the book from my nightstand drawer, and hustled straight back to The Hillside.

I walked up behind her and set the book down on the bar top in front of her. She looked down at the book, and then up at me.

“Now you don’t have to contact me,” I said.

She looked at the book again, and smiled. She recognized it.

“Thank you,” she said with a hint of gratitude.

“Take care,” I told her. She said nothing. I made my exit.

After nine years, the story had finally come to its conclusion.

After nine years, the story had finally come to its conclusion. After nine years, I’d closed the circle, I’d tied up loose ends, and I saw the first smile on her face since I’d told her I’d been in a hot tub in Eugene, Oregon.

I’d like to say that Linda forgave me, that she understood what had happened all those years ago. I’d like to think she was sympathetic about my tendency to self-sabotage. I’d like to say that she still had high regard for me, and even if I didn’t turn out to be the Best Guy In The World, I’d like to say she at least considered me a runner-up. I’d like to say that she wished me well. I’d like to say that we had a good laugh about it, and agreed to keep in touch. I’d like to say those things, but none of them would be true.

I would also like to say that I learned from my mistake, and made nothing but good decisions from there on out. The truth is, in the acceptance of being the Worst Guy In The World, I’ve made many, many more mistakes since I ruined things with Linda. My motto has become, “If it ain’t broke, break it.”

Sometimes people’s feelings are more important than the truth. But, the truth is all there is.