Guest Post: Emma and the Terrible Dates

This week’s post comes from Emma, who runs a YouTube channel called ‘Em telling it like it is’, which you can check out here.

I thought I’d share with you some of my worst dating disasters. The first is about how I dumped a total hottie on the first date.

The Milk Man

We had bumped into each other on a bus. More specifically, a night bus. Even more specifically, at about two o’clock in the morning, after my makeup had smudged everywhere from dancing all night. He was a mix of cute and handsome which is a look normally only found on a Ken doll, so when he asked for my number, I figured I’d say yes. I could easily ignore him or block him if it got weird. Which is my rationale whenever I start seeing someone new, but that’s not the point.

We went for tea, and the first date started off without a hitch, and with a LOT of points in his favour. He still had impeccable taste in clothes and I was only 10% worried he was gay – 30 points. He had a stable, high paying job he seemed to enjoy – 40 points. He was sweet, kind, funny and the epitome of a gentleman – 50 points. ‘So why in the world would you dump him?’ I can hear some of you shrieking.

Well, because our date went dramatically downhill from there, when he put milk in his tea.

Not that that would turn me off, you understand, but it turned his stomach right off. He was lactose intolerant! And he told me this as he watched me pour the milk into mine and wondered aloud if he should do the same. And, as I gently asked him why would do such a thing if he’s lactose intolerant, he poured the milk in anyway and started sipping.

Alright, so several thoughts passed through my mind at that point.

You don’t have to do everything that I do for me to like you!

Not putting milk in your tea isn’t a common deal breaker!

Is he actually lactose intolerant?

Maybe… he was exaggerating?

The date continued just fine… until we were walking back to the metro when what was bound to happen happened. So in as casual a tone as possible he suggested we stop by his friend’s place.

There, he built an entire love story with his friend’s bathroom, while I awkwardly hung out with the friend. And the friend’s mother. And the friend’s sister, of course. There was also a dog involved. Not awkward at all!

Just as I was about to call it quits, Prince Charming stopped flirting with Toilet, emerged, and started flirting with me. Great in theory, except it was more like he was talking about me to his friend… in front of me.

“Emma is just so sweet.”

“She’s so nice, right?”

“Isn’t she pretty?”

I’m not sure who was more uncomfortable, the friend or me. In any case, Prince eventually went back to his throne while his friend hurriedly assured me Charming wasn’t usually like this. And, thoroughly un-charmed, I booked it out of there.

So, yes, I basically caught Prince Charming with his pants down. And, no, I never went on another date with him. Even when he texted me on Valentine’s Day. Then right before Easter. Then again at Thanksgiving. And right before Christmas. I haven’t heard from him since so maybe he’s found his equally lactose intolerant Princess Charming. Here’s hoping!

The Student Crush

For my second story I’d like to rewind all the way to my college days. Picture a dorky but pretty, shy but hardly boring girl of 17 ready to explore romance, find ‘The ONE’ and easily settle down. Was I naïve? Very much so. Did I flirt with the cute bad boy? Yes. The one who already had a girlfriend? Yeah… but, hey, I can admit to not being perfect! Which is why we are going down this road. Or, at least, I am and you are somewhat blindly following. Just watch out for that tree!

One particularly memorable bad boy was named Bradley. And I thought the flirting was going pretty well, until his friend, who I’ll call Awkward Adrian, came over to me and asked me to back off. Which I did, with a lot of mortification, though I wasn’t really sure why he was asking.

I soon discovered the reason the next time Awkward Adrian, Bad Boy Bradley and I hung out.

See, unbeknownst to me, Awkward Adrian had feelings for me. And he kept saying lovey-dovey things to me, in front of my crush, Bradley. As though we were dating!

Things like: Sweetheart, when am I seeing you again? Darling, you look so pretty today. Yeah, I told Bradley about us, don’t be so shy!

I was sooooo confused that I really couldn’t muster up much of a defence. Or a counterattack. Or any words at all, for that matter. But, hey, in retrospect, maybe Awkward Adrian had just wanted me for himself all along, and was hoping that this was the way to win me over? Who knows?

All I know is this: men are strange creatures and should be approached with extreme caution. No petting, no feeding them snacks and certainly no direct eye contact. Maybe that’s why Awkward Adrian wanted me: I did, after all, feed him his very first clementine. I was concerned about him getting scurvy, you see.

A Few Other Encounters

You’d think that having a sense of humour would get me attention from the right type of guy. And that ‘The One’ would make all these creeps disappear like a dream come true. Well, at least, I thought it would.

But it turns out my sense of humour hasn’t always garnered me as much appreciation or love from men as I’d hoped. For example:

  • The time I was at a jock party and I scared all the men away from me. How? Easy. I actually said interesting things, made jokes and had my own opinion. Big no-no. Big turn-off, apparently.
  • The time I was flirting with this guy whose sense of humour only included puns. Soooo, he didn’t find me very funny and it took me at least 10-15 minutes to digest any of his jokes. Let’s just say my pun literacy is equivalent to that of a cat: it just doesn’t give a shit. And if you don’t understand my comparison, talk to a cat owner. They’ll tell you what’s up. And, no, I myself am not a cat lady. Not yet anyway…
  • The times I got ghosted. I mean, I don’t know if my sense of humour is actually why I got ghosted, but any hypothesis is as good as the next, right?

So, yeah, having a sense of humour hasn’t served me well. Nor has directly hitting on guys. Nor has waiting for a guy to hit on me. Nor has… anything, really.

What I Have Learned

Experience has taught me to be creative, and so now I have a whole arsenal of dating tools which includes:

  1. An invisibility cloak of ‘Oops, my phone hasn’t been working properly’.
  2. My Fictional BoyfriendTM for the overly persistent passers by.
  3. My confused mask of a facial expression when I’m being asked for ‘directions’. In the bonus pack, it includes its very own encyclopaedia of a fictional language which is mostly comprised of complete gibberish. Because I can claim not to speak English, Spanish or Dude-ish, when I need to.
  4. My trusty bike, when I work late. Ah, the joys of whizzing by wizards hoping to enchant me into their beds! And, yes, I’ve weighed up the risk of riding in pitch darkness over the risk of being accosted, thank you very much. I think I know which risk I’d rather take.
  5. My last recourse: using my purse (which weighs a few tons because, yes, I’m female) as a medieval weapon of doom.

And how has my dating life been recently? Let’s just say there have been a few more downs than ups, some more princes that dare not be mentioned, a few paupers that I’m not too sure I want to remember and a good few gaps of peace and quiet in between.

I also dated three people in a row who were adopted, and nearly dated a fourth. This is by no means a criteria that I look for in my dates – just a weird coincidence from the universe, I guess. Like the time I had a crush on three guys called Chris in a row. Also not a requirement, in case anyone’s asking.

I’m nearly ready to call my dating life well and truly dead… but I still reserve some hope. ‘Some’ being a very operative and very tentative word.

But, look, if there’s a real takeaway to all of my ramblings, it’s this: Princes and Princesses everywhere, don’t add milk to your tea and don’t try to hijack a person’s love. Please. Someone, someday, will love you just the way you are. For some of us, for now, that’s called family, pets and friends. But who knows what might be coming up next?

Emma is an actress, writer and the creator of YouTube channel ‘Em Telling It Like It Is’. Because artists usually wear many hats, one of which must be flamboyant. She tours yearly with Shakespeare Canada in Quebec, Ontario, New Brunswick and Nova Scotia. She also rarely sleeps. You can check out her video, A Modern Guide to Romance, right here, or take a look at her YouTube channel.



  1. Lu
    31st August 2019 / 6:08 pm

    Emma is hilarious,
    I love her style if writing:-) and sense of humour…
    Thanks Lucy for these Saturday morning reads,am always looking forward to them

    • 3rd September 2019 / 3:24 pm

      Hey! Emma here 🙂 Thanks so much! Lucy is awesome and I’m glad I got to work with her on this

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Names and some minor details have been changed to protect the innocent. And sometimes the guilty.
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