Me, Myself and Eye

Keeping it real on the first date proves that beauty truly is in the eye of the beholder.

I’ve never been one of those put-together girls. Oft denoted by glossy ponytails, they’re the ones who drink red wine and wear white without spilling on their clothes or staining their teeth. I couldn’t be further from the immaculately manicured kind; however, I’ve successfully sold myself on the fact that my general state of disarray is part of my charm.

And yet, if there ever is a time when I come close to approximating the polished Put-Together Girl, it’s when I’m First-Date Me. FDM is wrinkle-free (at least, she starts out that way). She fastidiously and discreetly checks her teeth for unsightly remnants and always appears interested in everything her dinner partner has to say—even when it has to do with the tedious details of a particular private-equity matter. She resists ordering fajitas because she knows that smelling like onions and making conversation through a cloud of sizzle-platter steam shouldn’t happen until date four. She’s a bit exhausting for me to be around, truth be told, which is why she’s only brought out for special occasions. 

One such recent occasion was a first date with an especially charming younger guy named Gabe, whom I’d met at a mutual friend’s party in the Mission. Gabe’s joke-making ability had entertained me to the extent that I’d ended up chatting with him in the kitchen for almost two hours. “You’re hilarious!” I enthused. “You should know, right now is the most you’ll ever like me,” he deadpanned. “This whole thing gets old—trust me.”

“I’ll take my chances,” I said, and gave him my number before leaving.

Gabe called two days later and left me a message: “Natalie, it’s Gabe—the hilarious guy from the party the other night. I’m calling to see if you’re free Wednesday. According to my facial-hair-growth chart calculations, that’s the night I’ll be the best looking all week. Hopefully you’re free—otherwise we could have an awkward-scruff situation.” After awarding him mental points for creativity, I called to accept the invite.

The morning of our date, I was feeling especially confident, thanks to a miraculously good hair day and a hot new dress I’d snagged on sale at Metier. But by the afternoon, my confidence had taken a dip: One of my eyes had randomly started to hurt, then water, then redden. “Have you been crying?” my friend Sara asked when we met for a late lunch. “It must be my allergies,” I told her, excusing myself to inspect the situation in the bathroom. When I looked in the mirror, I knew it was more than hay fever: My left eye was watering uncontrollably and had taken on a pinkish hue. With T–minus three hours until FDM transformation, I phoned my doctor for an emergency appointment. “It’s pinkeye,” he confirmed within two minutes of seeing me. “It is?” I gasped. “Well, look at your eye!” he chuckled. “It’s pink, wouldn’t you say?” I was less than encouraged by his cavalier diagnosis, but gratefully accepted the prescription eyedrops he gave me. With two hours to go before Gabe was set to pick me up, I met the girls for a second opinion. “It’s not that bad,” Jules said, unconvincingly. “Sure, the left one is a bit squinty, but it kinda just looks like you’ve been crying. It’s sweet, really—you look vulnerable.”

“I am vulnerable!” I said. “I’m about to go on a date without a trace of makeup and with my eye oozing fluid.”

“You could wear an eye patch?” Sia suggested, stifling a giggle.

“I hate you,” I said, knowing my decision had been made. Being at the top of my game—and my vision—was a mandatory component of any first date. I’d have to reschedule. I dialed Gabe’s number and debated making up a more attractive excuse, but realized at such late notice, anything less than the truth would sound as if I were blowing him off.

“I should have known when I got a great parking spot,” he said after I’d finished my frazzled explanation. “Wait, don’t tell me you’re already in my neighborhood?” I asked, looking at my watch and realizing it was just under an hour until date time. “I’m kind of anal about being on time,” he said sheepishly. “I’ve been browsing in the bookstore on Fillmore.”

“I’d come meet you, but trust me, this eye … ” I said, stopping short of doubling down on the word “infection” to my would-be date.

“Look, I’d much rather see you than not see you. Even if you can’t see me,” he said. “I’ll promise to look at your lips only.” His sweet reassurances were beginning to sway me. “Let me reassess the damage and call you back,” I said. I stepped toward the bathroom and heard “Man in the Mirror” playing in my head. Was I being ridiculous? I didn’t think of myself as a vain person, but the reality of going on a date without makeup and with ocular issues also seemed ludicrous. On the other hand, the notion of throwing my usual protocol out the window was sort of appealing—almost punk rock, like a middle finger to FDM. I called Gabe back. “Okay, you’re on,” I said. “But don’t say I didn’t warn you.”

I walked to Fillmore and met Gabe at the Elite Café. “I wouldn’t have even known!” he insisted, upon seeing me. “As preparation, I even made a mental list of all the weirdos I’d seen all day who were much less visually appealing than you, but now I see it was a waste of time.”

We grabbed seats at the bar, where I had a clear view of the mirror, should I need to use it for checking in on my pinkeye status. Gabe was clearly trying hard to make me comfortable—shouldering the lion’s share of the small talk that comes with first dates—but I found myself distracted by my increasingly clouded vision. “Hold that thought,” I said, and hopped off my stool to race to the bathroom for damage control. My eye seemed to be taunting me: Every time I rectified its flooding situation it would refill itself, like the bodily dysfunction equivalent of a trick birthday candle. I returned to Gabe, who was waiting patiently at the bar. “You okay?” he asked sympathetically. I didn’t even try to conceal my discomfort. “We both know the answer to that,” I grinned.

“You’re a champ,” he said. “Did I ever tell you about the time I went out with a girl who was a Siamese twin?” he asked. “Now that was awkward.”

Oddly, despite my general state of misery, it was a high to let myself so accurately reflect on the outside what was going on inside. I’d never had a more honest date: The eye malfunction set the tone for candid conversation—I’d completely bypassed the usual attempt at creating a mirage of perfection in favor of copping to real stuff and risking the possibly unflattering consequences. By the end of our second drink, however, I had developed an unshakable cough—I was clearly coming down with something. “This is sort of exciting—like, what’s going to happen to you next?” Gabe asked, feigning suspense.

“I think I know what’s going to happen,” I said. “I think I’m going to put myself to bed.” After good-naturedly offering to assist in the process, Gabe paid the bill and walked me home. “I had a good time,” I said, adding, “And considering my situation, that’s a serious compliment to you.” This was the part of the date when the first kiss would happen, but I wondered whether Gabe would attempt it, considering the blinking hazard sign I had become. He leaned in and gave me a kiss on the cheek. “I’m coming back for more when you’re better,” he said.

I climbed the stairs to my apartment and made a beeline for bed, never more happy to rest my eyes. Privately, I felt a sense of accomplishment, similar to when I was little and lost a tooth—as though I’d tangibly grown up a bit that day. And yet, there was something unsettling about the fact that the most “un-me” thing I’d done in a while—soldiering through a date sans a trace of FDM—meant that I’d never been more myself right off the bat. Unsettling enough, perhaps, to retire FDM

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