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Authors: Jennifer Tress

BOOK: You're Not Pretty Enough
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“Three hours seems like a long time to hang out with people you see a lot, don’t you think?”

“No.”

“I mean, and I don’t want to upset you, it’s just—don’t you think everything that needs saying can be said in three hours?”

“What?!”

“I just want to spend time with you, that’s all.”

“WE DO. I was with you last night and the night before and today at fucking lunch! Jesus!”

“Please don’t be mad.”

I felt trapped. Yet I still stayed in it because I didn’t want to hurt his feelings. How many ridiculous situations did I put myself through because I didn’t want to hurt someone’s feelings or because I was
avoiding a tough discussion? Or because I thought that opting
not
to be with someone = being alone for the rest of my life?

When I needed a new place to live—quickly—Josh suggested I move in with him and another friend of ours, Kristin, who was
lovely and worked with us as well. I said yes and signed a year lease for a move-in date two months later.

*********************

About a week after that, I attended a mandatory conference
in Washington, DC for all new consultants at the firm where I now worked. It was highly professional but also included playtime. The conference was Sunday through Friday and taught us about how to work with clients and in teams based
on our Myers-Briggs scores. At night, we had “homework” but were also allowed to pal around with the three hundred or so other consultants in attendance from around the country. I meshed well with a guy from Boston who was a couple years
older, Michael. He was Ivy League educated, a former pro-athlete, and really, really good-looking—someone I considered waaaay out of my league—and he spoke the language of that phase in my life: sarcasm. After the conference, we stayed in touch.

HIM, 7/27, 4:10 p.m.

Hey, you saw a great baseball game back in Cleveland on Friday night, huh? I hope you stayed to the end…!

ME, 7/27, 4:24 p.m.

I never made it to the game (plane was delayed), but I did
meet up with friends. Nothing tops off a week of drinking like a weekend of drinking. I’m pretty sure my efforts to destroy my liver were far healthier than your sissy hiking adventure. How was it?

HIM, 7/27, 5:21 p.m.

My “sissy hiking adventure” is next weekend. PAY ATTENTION, JERK! I merely made mention of it because a) you are a dullard, and as such it is especially difficult to carry on a conversation with you, and b) a trip of
such magnitude requires significant orchestration, so I must plan well in advance.

Do you hike? You mentioned you like the woods (er, and the ocean?), but I couldn’t tell if you were a true nature lover or if you were just
humoring me.

ME, 7/27, 5:40 p.m.

I am a nature lover. Like one time I watched a special on the Galapagos Islands on the Discovery Channel. I also like granola. Yep, they
call me “nature girl” around here. Is this thing on? (Simulation of trying to tell jokes to a silent crowd and tapping the microphone, just in case you’re a “dullard.” And, by the way, please quit using words that make you appear smarter than me. Thank you.)

Seriously, though, I love outdoor activities, but don’t necessarily seek out adventures that keep me away from electricity for more than three days. I went to Aspen last October, so I spent a lot of time hiking there. Climbed up mountains and gazed at the Continental Divide. The mountains
made me cry. I’m not joking, jerk, so quit yer laughin’. During the summer I spend a lot of time on the water, and as I mentioned, I have a long love affair with the ocean. Always enhances whatever I’m feeling at the moment. Now don’t
go thinkin’ I’m some sort of sissy girl. I’m tough, I tell ya—tough as nails!

Re: your hiking trip NEXT WEEKEND, if someone asks you a yes/no question and you answer with “does a bear shit in the woods?” there
actually may be a bear shitting in the woods.

HIM, 7/28, 9:37 a.m.

Actually any yes/no questions will be answered with “do
I
shit in the woods?” So you’re a nature girl? Crying on mountaintops? What a
friggin’ baby. Actually, I see you as a slightly older, more robust Laura Ingalls, running down the grassy hillside to particularly poignant music, the wind gently tossing your pigtails, one hand holding a daisy and the other a lit
cigarette. Let me know how the presentation went.

ME, 7/28, 10:53 a.m.

You’re pretty much on target with your description of me.

HIM, 8/1, 9:13 a.m.

Some immediate thoughts on our correspondence: First, you’re
very funny. Much funnier than you appear to be in person; in fact, I almost wish I never met you—that way I wouldn’t have to meld this image I have of you as a chain-smoking lunatic with the lovely, bright, witty person that is
depicted on my monitor each day…

Here’s a question for you…On a scale of one to five, with one being “Strongly Disagree” and five being “Strongly Agree,” how would you respond to the following statement:

I have a boyfriend.

**********************

So that thing starts to happen, right? That thing where you realize you’re starting to go down the wrong path? I could
see
that I
was starting to like this guy and was looking forward to connecting with him, often multiple times per day. I could
see
that I was starting to play with the truth. Yet I justified continuing because
we’re just e-mailing, right? It’s not like there are any expectations here, right?

ME, 8/1, 1:52 p.m.

I would have to choose two, meaning Disagree. I am
seeing
someone but would not place it in that boyfriend/girlfriend thing. It’s more of
a “I’m feeling buzzed, do you want to make out?” sort of thing. Though he is a very nice, fun boy. And you?

HIM, 8/1, 2:03 p.m.

Now I’m feeling as happy as a little girl…I don’t know where
that expression came from—is that a Sprockets thing? What am I missing? As for me, I too am a very nice, fun boy. And I’m a one. And I’ve been feeling very buzzed (of course, the liter of Dewars hidden in my desk has helped somewhat). Hmmm…

Now is what I like to call “work time.”

********************

It went on like this: Michael and me e-mailing, then talking on the phone, and then making plans to see each other—though, in the
beginning I was noncommittal because all the while, I was thinking to myself,
YOU ARE MOVING IN WITH JOSH AND KRISTIN IN A MONTH. WHAT THE HELL DO YOU THINK YOU’RE DOING?

Well,
self replied,
you’re creating an untenable
situation that will blow up in your face.

That’s right! Thanks for the clarification.

HIM, 9/5, 10:27 a.m.

Have you decided on Boston? I’m trying to think of what a
first-timer would like to see…There’s Beacon Hill (cool, hilly residential area where Cheers is), the North End (Italian food, mafia), the Freedom Train stuff (Old North Church, Bunker Hill Monument, etc.), Harvard Square (Hippies—you’d like that), Fenway Park (beer, dogs, ball). We could also go to the Cape (read:
the Ocean), or better we could fly to Nantucket or to the White Mountains in NH. That is, if you’re still coming.

ME, 9/5, 10:46 a.m.

The Ocean is a definite. Does it make you nervous? I’m
really nervous.

HIM, 9/5, 12:23 p.m.

Let’s go to Nantucket; you’d love it there. It would be nice to get on some neutral ground, so to speak. I am a little nervous but mostly
because I’m not confident you’re committed to coming. Whatever. If you dis me, I’m going anyway. I could use the towels.

ME, 9/5, 5:37 p.m.

I booked the flight. See you in two weeks.

******************

I wasn’t
completely
delusional. I knew I’d have to explain my leaving town to Josh at some point, so I just ripped off the bandage and told him the truth one night. Sort of.

“Listen, I’m going to visit someone I met at the consulting conference. That guy I told you about. We’ve become friends.”

“Hmmm, I’m not sure I like that.”

“Yeah, well…”

“Where are you staying?”

“In a hotel.” Which, you know, I
was,
just in Nantucket…with someone else.

It’s a testament to the strength of the mind how easy it is to rationalize your actions even when you know they’re wrong. Even though Josh
and I were no longer physical—something he accepted—I kept him on a long leash, as a “backup” in case things didn’t work out with Michael. I wish I’d had the strength to sever any romantic notions compassionately but firmly.
I wish I’d had the strength to say, “I’m not moving in” and just deal with the consequences, to not be afraid of “the unknown.” Instead I was a coward and convinced myself that because I was being “honest” I was being fair. But just
because you’re transparent about treating people poorly doesn’t mean you’re not an asshole for doing it.

******************

Boston was magical. Michael picked me up at the airport, and we went back to his apartment, cracked open a bottle of wine, and fell into a
dreamy spell of conversation and making out. The next morning we headed off to Cape and took the ferry to Nantucket where we had great meals and great conversations. We rented mopeds and traveled around the island, marveling at
the expansive homes with their distressed gray shingles and pristine landscaping. The tone in our virtual correspondence transitioned effortlessly in person, and this left us both feeling open, relaxed, and excited. We shared many tender moments, including a long, lovely kiss on the shore of the ocean.

But it was not perfect. He showed signs of relationship sabotage by pointing out that long distance affairs were hard and might not be worth it in the long run (while we were in each other’s presence for the first
time—the first time!). And while he took care of me in the bedroom, he would not let me reciprocate. Instead I kissed his face and neck for ten minutes straight. He said, “Can you please do that forever?” I wanted to.

****************

As luck would have it, he got a project in Cleveland and I got one in Boston, and because work paid for a hotel, I’d stay with him and vice versa. It felt like a mini getaway, a fantasy even in my own city, and I’d
just lie to Josh about where I’d be and drum up reasons to avoid bringing Michael over to my place to meet my roommates.

“Ahh, that place is always a mess. Plus, remember how I told you Josh gets weird when I’m around other guys?”

“Oh…OK…”

We decided that in order to take our relationship to the “next level” I should move to Boston. We talked about where we’d live, what jobs we’d have, and how much we missed each other and wanted our lives together
to start NOW.

This will blow up in your face soon.

[Me putting a pillow over my conscience’s face]
Shhhhhhhh. Don’t fight it.

********************

As is usually the case, things have a way of catching up with you. Michael was growing impatient with me and my inability (or unwillingness?) to make progress on our plans.

“Have you called [so and so]?” he’d ask.

“Uh…on my list to do today….”

“You said that yesterday. And the day before.”

“Today. I promise, today.” I did want all the same things, sincerely. I just wasn’t ready to move to Boston
for a guy.
He was the
only person I knew there (I hadn’t met any of his
friends yet either, come to think of it). It felt scary and risky to put all my eggs in that basket. After the divorce, my mind shifted into a logic machine:
what if,
what if, what if
? There were too many what-ifs.

And of course the living situation with Josh was not ideal.

“Why are you letting this ‘friendship’ with Josh impede our relationship?” Michael asked one night.

“I’m not. I’m just trying to be sensitive to his feelings. It’s hard when one person has a crush and the object of the crush doesn’t feel the same way.”

God, you’re an asshole.

Shhhhhh.

“You’re not doing anyone any favors. You’re part of the problem, you know.”

“I know.”

In late November we took a getaway to an island in the
middle of Lake Erie called Put N’ Bay. I told Josh I was going to hang out with a friend who lived there (which I did, but I didn’t see her). We connected deeper, on a level that made me feel like I had found “the one.” I decided it was time to come clean and move out. Turns out The Universe felt the same way.

We had three hours from the time we arrived back in Cleveland on Sunday until Michael had to catch his flight. On the drive back from the island, I tried to think of things we could do to kill time.

“Want to go to the Rock Hall?” I asked.

“You know, I hate to keep bringing this up, but it’s odd that I haven’t been to your place yet,” he said. “My friends think it’s kind of
absurd, actually. We’ve spent plenty of time at mine, and I don’t like having to imagine what your sleeping situation is like.”

“Well, how about we just drive by?”

“Fine…we’ll drive by, weirdo.”

And so we did. And as we’re approaching, I saw Josh coming
to the curb to take out the trash. We locked eyes, and all my options flashed before me.

Should I duck?

No, no, no. That’s wrong.

OK, so…? Running out of time here!

Pull in.

“Well, there’s Josh” I said to Michael.

“Great, it will be good to meet him actually.”

[Begin slow motion reel]

We both get out of the car and Josh is looking at me like
what the fuck?
and Michael approaches Josh and warmly extends his hand, and Josh takes it and says, “What have you two been up to?” and Michael says “Well, we
were just in Put n’ Bay and had the best time,” and Josh says, “Oh, that’s cool,” and we all head into the house, and Michael goes to use the bathroom, and Josh says to me, “Wow…you’re a real asshole,” and I say, “I know, and I’m
going to take him to the airport right now,” and then Michael comes out of the bathroom and sits on the couch and starts talking to Josh about the football game that’s on TV.

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