Diary of a Hopeless Romantic: Dreams, Disappointment, & One Double Date

I thought that when my best friend started seeing the guy who lived down the hall, I’d get to meet a whole slew of relatively attractive, newly independent, slightly older men who found my youth and obvious (attempts at) charm endearing and just the right amount of sexy. Much to my surprise, my little romance novel fantasy actually materialized more quickly than I thought: I sparked a connection with the best friend of the guy next door within a month, and through some weird rom-com twist of fate, he wanted to take me out on a date. My dream meet-cute was a success!

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Or so I thought.

Instead of going on an old-fashioned one-on-one date, which is what I thought he meant by “hey, do you want to go on a date with me?” he decided that a double date would be more fun. Okay. That’s not exactly what I wanted, but maybe it would make getting to know each other a little easier. I could find a friend for his friend and it would be my first double date and it would still be magical. No problem.

Find a friend I did, and with zero hesitation we pulled a Cher from Clueless and like totally got new outfits for our mega-awesome double date to show how completely capable we were of casually double dating. Of course we contrasted that chillness by spending the next week obsessively texting back and forth about how terrified we were, especially since neither guy had actually set a date for our date yet. But in my head, this was still the ideal potential-boyfriend situation, so I played it cool(ish) and patiently waited to hear from him. The next weekend, I finally plucked up the courage to shoot him a text to ask what the deal was.

“Want to go tomorrow?” He asked.

“Sounds good,” I replied.

*insert Grey’s Anatomy inspired 10 second dance party here*

When my doorbell rang on that fateful night, I was completely soaking wet with sweat, but my hair looked good, and that was all that mattered. I opened the door to his smiling face, and admired his button-down and khakis with the same silent joy that a 7th grader harbors for her crush.

From there, things get a little shaky. We had a pleasant conversation during the (45 minute, I know) car ride to his house and I felt hopeful when I stepped inside his front door to a tidy and well-decorated space. While he changed clothes, (why, I don’t actually know, and I didn’t realize that was weird until way after the date ended) I sat at his kitchen table and stared at my phone until his friend and my friend walked through the front door. I didn’t know his friend, but I quickly picked up on a tension emanating from my friend’s puckered expression. When he opened his mouth and immediately started talking about himself and how much he loved his outfit, I understood why.

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After spending about 20 awkward minutes trying to come up with a place to eat in town (because neither man actually thought about where we would go or what we would do on this date), we piled into my date’s car and pretended to all like the Counting Crows song that was playing on the radio. I was incredibly uncomfortable, but chalked my anxiety up to first date nerves, and focused instead on how to make my friend happy.  Her date, whom I shall now refer to as Negative Ned, was spewing crap about his fancy New York job and how much he hated it despite making tons of money. Nobody cared, nobody responded, and still he talked. I looked at my date with the hope that he would swoop in to shut his friend up and say something witty to make me stop sweating, but he didn’t.

At dinner, Negative Ned was worse. The restaurant they picked was a tiny Italian joint where the tables were practically on top of each other and the food could have come from the frozen TV dinner section at Shop Rite. We waited for about 25 minutes before finally sitting down, and during that time my date went to the bathroom four times. Every time he left, Negative Ned would sigh heavily, and only speak to my friend, leaving me leaning against the wall longing for an escape plan.

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Finally we were seated and given thick plastic menus; I studied mine like it was the SAT answer booklet. At long last, my date spoke up. And for the first time that night I felt like this could work. While Negative Ned kept draping his arm over the back of my friend’s chair much to her blatant disgust, my date, let’s now call him Positive Peter, would ask both me and my friend questions about ourselves and our lives that we actually wanted to answer. We played those silly “would you rather” games and talked about the three things we would want if our plane ever crashed on a deserted island. He shared with us his deep “life means this” revelations, and though I didn’t always agree with what he said, he was still way more interesting than I thought he was just 30 minutes before. He was kind, and funny, and considerate. It just took him awhile to peek out from his shell. He still went to the bathroom, every 15 minutes, though.

Positive Peter’s sudden sociability made Negative Ned ten times more negative. I won’t go into all the boring details of his bad attitude (poorly-timed sex jokes, inappropriate touching, lack of respect for women in general), but it hit its peak when Positive Peter turned to explain something to me, and I saw Negative Ned lean into my friend’s shoulder to whisper something that made her face explode with silent rage. When he got up to take a phone call five minutes later with a sour puss on his face, and Positive Peter was in the bathroom for the 112th time, I asked her what he said.

“He asked me if I wanted to get out of here…” followed by a long line of obscenities that I wouldn’t write down, even on the internet.  Despite my friend’s clear desire to get out of there (preferably with me, not with Ned), we had all agreed before dinner that bowling would be a great way to round out the night, and no one had the courage to stop it. I was exhausted and miserable and wished I didn’t just eat two pounds of penne vodka.

By the end, everyone was itching to get away from each other. Luckily for my friend, she had driven herself to Positive Peter’s house, and as soon as we returned, she hugged me, shouted “peace out” to Negative Ned, and drove away like a bat out of hell. Apparently realizing that he wasn’t going to get any from anyone, Negative Ned sulked off, never to be heard from (by me or my friend) again. Good riddance. I climbed back into Positive Peter’s car and gritted my teeth for the drive home. At least my half of the date was going… relatively well?

But then, for the 45-minute ride back to my house, Positive Peter talked about love. He told me what he believed love is, what it meant to him, and what he wanted from it in the future. It was beautiful. I had never, ever heard a man talk about love the way he did. I wish I wrote it down, actually, but I was so completely caught off-guard that all I could think was: Did I get it all wrong? Was this entire night actually a success? Did he, heaven help me, did he love me?

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Nope. He didn’t even kiss me goodnight, barely even hugged me, in fact. I sat in the front seat for two seconds too long after he gave me an awkward side hug and turned away, then I finally got it together and leapt out of the car. I walked into my house without turning back, and crumpled into a heap on my bed before calling my friend to digest the evening. We both agreed never, ever again (we even went so far as to sing Taylor Swift’s “We Are Never Ever Getting Back Together”) and I went to sleep pretending like everything was fine.

Because it was. I woke up happy in my own bed, still single, and still optimistic that my next date would go better. Maybe I put a little too much pressure on the night, but what hopeless romantic doesn’t? Lesson learned. But that still won’t stop me from starting to plan my next date-outfit.

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2 comments so far


  1. OMG! That is slightly horrific. But at least you and your friend got to rock a T-Swift song. 😛

  2. SamiNuke4

    That sounds like such a bad date!! But it was fun to read 🙂

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