The Good, the Bad, and the Awkward: 5 First Dates I’ll Never Forget


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Dating is so weird. It simultaneously triggers my anxiety and makes life seem beautiful. It’s an antiquated practice but still feels fresh and crucial. Good dates can be amazingly, astonishingly good, and bad dates can be unendingly, unforgettably bad.

Dating and hookup sites like make it easy to find dates plentifully and quickly, but after a while, sometimes all those trepidatious evenings start to blur together. There are, however, some dates I’ve been on that I will just never, ever forget. Whether memorably marvelous or memorably mortifying, here are five dates that will stick in my head forever…

My first date ever was with a boy I met on DeviantArt (ugh, god, I know!). A high schooler already, he seemed devastatingly wise and cool to my dweeby middle-schooler ass. We met ostensibly to trade photography tips and wander around Kensington Market taking pictures, but first we made a pit stop in a nearby Burger King to fuel up for our mission.

It’s normal for conversation to be stilted when you first meet someone in person, as you both shake off first-date jitters and get to know each other’s conversational rhythms. But sometimes that rigidness just doesn’t go away. This was one of those dates.

After waiting in line to buy our food and finding we had damn near nothing to say to each other, we sat down with our burgers and fries and tried not to look each other in the eyes. Mid-bite, he shook his head sadly and proclaimed, “This is exactly the kind of awkwardness I was hoping to avoid.”

Needless to say, there was not a second date. I think he later came out as gay – which might explain our lack of romantic or sexual chemistry, but not our lack of conversational chemistry. Dates can still be great even if they end up veering less romantic than expected – I’ve made some of my closest friends that way – but that was not the case here. It was, shall we say, not an auspicious start to my dating career.

2267570972_b6771af296_oMy first good date was with a gorgeous, goofy, purple-haired lesbian I’d had a crush on forever. The week previous, I’d confessed my feelings in a handwritten note containing lovelorn excerpts from my journal. My crush was reciprocated, and now, tentatively, she was my girlfriend and I was hers. It was the most exciting and terrifying thing that had ever happened in all my fifteen years on earth.

We met at her favorite coffee shop, Chocolate Heaven. My cafés of choice at the time were Starbucks and Tim Hortons, so this cozy indie haunt seemed as refreshingly quirky as my new girlfriend herself. She ordered a cappuccino and I swooned; what a cool thing to drink, I thought. I ordered a hot chocolate and my hands shook so much, the mug clattered in the saucer.

We talked for hours. We couldn’t stop talking. Her synapses fired so quick, it was like riding a roller coaster of puns, anecdotes and retorts. Her eyes flashed brightly, her hands swirled in wild gesticulations, and she spun clever yarns I devoured with fervor.

When we couldn’t reasonably linger in the café any longer, I walked her home. On her porch, I rocked back and forth on my heels, shoved my hands in my pockets, hemmed and hawed. I’d never received a kiss; how could I be so bold as to initiate one? But somehow I did. I leaned in, and – ouch – our foreheads collided. We tried again. My nose crashed into hers. “One more time,” she giggled, and we gave it another shot. That time, it worked. I skipped home like the smitten idiot I absolutely was.


One night in 2009, a boy rang my doorbell. I answered the door with tears in my eyes. He was the reason I was crying, and he knew it. He’d betrayed my trust, and I was crushed, in more ways than one.

I said his name when I opened the door, surprised to see him. “I really like you,” he blurted in response. This was new information to me. “Would you maybe wanna go out with me sometime?”

“Let me get my coat,” I managed to respond, the tears already drying on my cheeks.

We went to a nearby café. I ordered a chai latte, which he insisted on paying for, in that dorkily chivalrous way teenage boys have. As we waited for our drinks at the bar, I chirped, “I can’t wait to call my best friend and tell her I went on a date with you! She’s gonna freak out.” He grinned and replied, “Why don’t you call her right now?” He was a weirdo. It’s one of the reasons I liked him so much. I took my phone out of my pocket and dialed, unable to stop smiling.


My most life-changing date was in March 2011, and I didn’t even want to go. It was my first time meeting an OkCupid suitor in person, and I was nervous about any and all possibilities: nervous our conversation would be awkward, nervous he’d think I was ugly, nervous he’d be an axe murderer. I asked my best friend to casually “drop by” the tea shop where the date would take place, about midway through, so she could save me if I needed saving.

As it turned out, I had no reason to worry. I showed up and found that the boy was charming, smart, witty, and kind. We geeked out over Pokémon, bemoaned the shortcomings of OkCupid, and laughed at each other’s weird jokes. When my friend stopped by to check on me, I told my date that she was doing this and why, and he was completely cool with it. He understood. We bid my friend adieu and my new cutie walked me to my doorstep.

We didn’t even kiss on that first date, and that is why I will argue ceaselessly with anyone who claims a first date has to end with a kiss or the match was a failure. That man ended up becoming my first serious boyfriend, my first love, and my portal into new worlds. We took things very, very slowly, and I’m glad. That first date was just as effortlessly delightful as the rest of the relationship. I don’t regret a bit of it.

tumblr_nnsjpdxtr61qzigipo5_1280My first Tinder date was with a cute comedian. I met up with him at a sketch show, breathless and late. “What did you do today?” he asked, conversationally. “Oh, I was working on a post for my blog,” I told him. “What was the post about?” he asked, and I had no choice but to tell the truth: “Um, it was about my clit.” He reacted, I should say, admirably well.

The show was so funny I repeatedly choked on my beer. Afterward, I asked, “Do you wanna hang out for a while?” and he said, “Yeah, I really do.”

We sat in the dim scuzz of Comedy Bar for hours, asking each other questions about our childhoods and favorite movies and online dating experiences. Eventually we meandered to McDonald’s for some food. I remember he complimented my blue tights and asked if he could touch them. I think that was the moment I decided I wanted to have sex with him. And later, I did.

It’s funny how, even though that relationship ended terribly, the first date still shines in my memory. Sometimes a first date is a preview of the magic to come, and sometimes it’s the only magic the two of you will ever conjure together. Either way, good first dates are worth appreciating: they are preciously rare in this world.

What are the most memorable first dates you’ve been on?


Heads up: this post was sponsored, but as always, all writing and opinions are my own!