date girl

letters to dates past

dear pear guy…

dear pear guy

Dear Pear Guy,

“I’m so glad you look like your photos,” you said, in a way that suggested that definitely wasn’t always the case.  You were cute in that skinny tattooed skater kind of way.

After a drink and the obligatory first date nerves, we got out of our own way and the night disappeared in a glorious blackhole of conversation, vodka and good food. You texted me as soon as we parted: “You’re so lovely.” You were unabashed with your feelings and I liked it. A lot.

On our second date, we watched 500 Days of Summer and you stroked my hair like a cat. On our third date, you introduced me to your friends. “They like you better than they like me,” you said afterwards.

There was no fourth date, only a message saying you felt like you were dating “above your station” with me. The old you deserve better charade.

I was on a new date when you texted, “Do you like pears?” Dumbfounded, I replied that I did. “I want to make you a cake,” you said.

Three days later, no word and definitely no cake. I called you out on it. You said you burnt it.

You messaged me on NYE and said you wished “all good things” for me. I tried to wish the same for you.

Date Girl. 

dear accountant guy…

dear accountant guy

Dear Accountant Guy,

My brain, on you:

  • Cute (good eyes, good arms)
  • Polite (manners, treated the wait staff well, etc.)
  • Doesn’t drink (good thing? Not sure)
  • Chose good venue (city, underground small bar)
  • Has solid career (accountant, big $$$, but doesn’t like job)
  • Goes to gym regularly (hence the arms)
  • Owns studio apartment (in Darlinghurst)
  • Similar age (26)
  • Close with family (but not too close, they live in Newcastle)
  • Genuine (appears to have decent motives).

My heart, however, would not have a bar of it.

When you asked me out again, I said I didn’t think we were a good match and that was the truth. I was mad at myself for a while, but now I try and remember the above conflict for when I get rejected myself.

Date Girl. 

dear model guy…


Dear Model Guy,

I thought you’d be a fake profile. Guys as beautiful as you don’t need online dating. But there you were, leaning against the brick wall outside the bar looking like the goddamn cover of Vogue.

I got a wine and you got a beer. You only drank half.

“I don’t really drink. Too many calories,” you said. I guessed we weren’t eating, then.

You were new to Sydney from New York, looking at the city through a bright and shiny new lens. You ranted about America. I nodded along. You didn’t ask about me once.

People openly stared at us when we walked down the street. You, because you’re a model, and me, because I was with you. The attention was foreign and oddly exciting.

Down by the harbour, you complimented my eyes as well as a few other physical attributes. You only got away with that lack of subtlety due to your exceptional cheekbones.

I saw you again, I blame the cheekbones etc. I was your one-woman audience and you lapped it up. There were several rain checks on the next date.

A month later, you sent me a message on Facebook, asking for feedback(!). Judging by the generic nature of the message, you’d sent it to a not-so-select few. You wanted to know why I lost interest and how you could improve. I didn’t reply.

Date Girl.

dear jazz guy…

Dear Jazz Guy,

I hadn’t even known you for two minutes before you asked, “Have you ever felt trapped in a relationship?” I said no.

“So you just bail as soon as things get hard?”

“No, but I know when something’s over”

Having exhausted that very intense early date topic, you gave me a run down of the history of Jazz from 1930 to 1950.

We sat surrounded by sandstone in a New York-esque bar, while a musician set up his instruments. The musician took a liking to you and bought us drinks. He wouldn’t stop talking to you about his teenage daughters and how they’re growing up too fast. It soon became a date for three. You, me and the middle aged muso. 

Eventually, he played some jazz, which you were quick to point out as mediocre. 

As one song ended, we left, did the awkward ‘nice to meet you and nicer to never see you again’ thing and parted ways. 

Date Girl. 

dear staring guy…

Dear Staring Guy,

Going to the Marina Abramovic exhibition for our first date was your idea.

We queued up and had five minutes of hurried conversation. You told me you were currently going through a phase of listening to Louise Hay audiobooks, and I found your honesty disarming.

Once inside the building, we put on our noise cancelling headphones and you took me by the hand. We walked toward the white booths and sat down on the plastic chairs, facing each other. We stared at each other. And stared. And stared.

After an eternity, you took off your hipster glasses. That was a whole new ballpark. I felt like I knew you more intimately than guys I’d dated for months. I wondered if my eyes were giving away more than I wanted to. 

We finally broke eye contact and exited the building. We had been staring at each other for 45 minutes. 

Outside, you felt unfamiliar and it was jarring. We bought two soy flat whites from the cafe and sat down on the edge of the pier. As usual, I took forever to drink mine.

You said I was hard to read, and should smile more. I was a bit taken aback, but liked your directness. 

You wanted to stare at each other again and I obliged. After a while, I closed my eyes to get some space. I felt your lips on mine, a sneaky kiss. 

Another hour passed before our goodbyes. I walked through the Rocks on a high from our secret mission. 

I saw you one more time and when you left you were a picture of cool: “See ya round, darlin’.”

I never heard from you again.

Date Girl.

dear shoulder pat guy…

Dear Shoulder Pat Guy,

There were no seats available, so we had to stand up in the middle of the bar the entire time. You acted totally disinterested, but kept wanting to get another drink. I think you were doing the whole ‘I’m-so-cool-that-everything-bores-me’ thing.

I wanted to like you, I really did. But you made it so hard. You kept putting down my career aspirations, saying it was a “terrible industry” with “no work”. Possibly true, but let a girl dream, please. You told me how well you were doing career wise, and how it would take me “a long time” to get to where you were at.

I told you I had a dinner to get to, and you seemed oddly disappointed. I thought you hated me, Shoulder Pat Guy.

We walked outside and it was clear you were expecting a goodnight kiss (were you on the same date as me?). Between making me feel like I was terrible company and the smell of alcohol on your breath, I could only bring myself to say goodbye to you in one way. I patted you on the shoulder.

I don’t think you liked that, as when I went onto Tinder you had ‘unmatched’ me.

Date Girl.

dear fish coaster guy…

Dear Fish Coaster Guy,

You were doing SO WELL until the fish coaster. You took me to amazing restaurants, you bought me flowers, you sent me thoughtful texts (although the “How is your nap going?” one was a little worrying – if it’s going at all, I CAN’T REPLY).

We stayed in regular contact when you went to the Bahamas for work. The resort you were at was insanely luxe, you lucky thing. You came back and we went out for dinner. You reached for your bag and said, “I got you this, but I’m not sure what it is.”

You pulled out a wooden, brightly painted coaster in the shape of a fish. An angel fish, no less. I wish I could’ve seen my own face, and I’m sorry that you had to. I examined this thing when I got home. It doesn’t even fit a drink on it. What do you do with ONE fish coaster that doesn’t fit a drink? I’m thinking of framing it, actually.

You have a lot going for you, Fish Coaster Guy. You are lovely and genuine and if my feelings toward you had been stronger, we would’ve worked past the fish coaster. 

Date Girl.        

dear pictionary guy…

Dear Pictionary Guy,

You were all Dutch accent, floppy hair and lack of social awareness. You pulled a notebook and pen from your bag and said, “Let’s play Pictionary”. If I looked shocked, you didn’t notice. We hadn’t even ordered a drink yet.

“I’m thinking a native animals theme,” you said as you started to draw. A round fin appeared.

“It’s a dolphin.”

You looked hurt. I’d beat you to the punch line. You didn’t stop, though. Koala, kangaroo, echidna, platypus, butterfly.

The kind waitress brought us drinks. They weren’t nearly strong enough for this.

You finally handed me the pen. We were out of native animals, so I drew a rabbit. You got mad: “That’s not native”.

When you left to go to the bathroom, I did two things: I took a photo of the piece of drawing paper, and I texted my roommate asking him to bail me out with a phone call. I do feel bad about that.

I told you my roommate was locked out and I had to go home to let him back in. You totally knew I was lying. And my immediate karma was having you ride the same bus back to the station with me.

The only thing we needed to make the night more awkward was fluorescent lighting, and the bus delivered.

Date Girl.

dear sleazy emoji guy…

Dear Sleazy Emoji Guy,

My god I love a guy that uses emojis. And your misuse of the ‘sleazy face’ emoji was my favourite. For a while I thought you were being very suggestive, saying things like “I’m alone in the office smirking-face

But then, when you continued with messages like “Got caught in the rain again smirking-face” and “Got a phone call and now my dinner’s cold smirking-face” I realised you thought it was an annoyed face.

That, or you have a really sexy dinner.

Date Girl.

dear camo guy…

Dear Camo Guy,

You wore camouflage shorts to a fancy bar. You told me you were late because you were drinking beers with your mate and had to take the back roads so you didn’t get caught. “But don’t worry,” you said, “I’m really good at it.”

Your mum lost her license recently for a DUI. “It runs in the family,” you laughed. You were about to order shots before I declined.

I didn’t last long, with you. Just long enough for you to tell me you were online dating because your mates “were getting so much sex from it”.

I said I had an early morning and had to go. You offered me a lift home(!). I declined.

Looking back, I still find the camouflage shorts the most offensive thing about the night.

Date Girl.