9 Unwritten Toronto Dating Rules Every Newcomer Should Know Before A First Date

Whatever you do don't split the bill.

Brooke Houghton at Piano Piano. Right: The CN Tower.

Brooke Houghton at Piano Piano. Right: The CN Tower.

Dear Brooke, I just moved to Toronto from India and am starting to explore the dating scene. What are some things to avoid doing on a first date in the city?

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Welcome to Toronto and congratulations on your move!

I don't know what dating in India is like, but dating in Toronto is like running through a raspberry bush naked and praying you find a sweet little snack without enduring too much pain.

Ok, maybe I'm exaggerating a little – it's not that bad here.

Dating in the city is a wild ride, and I'm here to be your guide in this jungle of love.

I've been dating in Toronto for almost two years, and I've been on my fair share of good and bad first dates.

A first date isn't a big deal, but it can make or break a possible connection. I think of first dates as a soft interview. You want to get to know their likes, dislikes, learn a little history and see if they'd be a good cultural fit in your life.

Remember, as much as you want to be polite and make a good impression on them, they should also excite you!

So before you go on your first big date and paint the CN Tower red, here are a few things I'd recommend you avoid.

1. Don't ghost before the first date!

A woman texting.

A woman texting.

Diego Vito Cervo|Dreamstime

​Toronto is a busy city filled with busy people.

If you don't confirm a date, most people are going to assume it's not happening.

The morning of the big event, shoot your date a casual text like, "Hey, looking forward to tonight. Are we still good for 7 p.m. at (insert location here)?"

If they don't reply, don't bother showing up – chances are they won't be there.

2. Don't just walk into a restaurant 

If you're going out on a prime date night like Thursday, Friday, or Saturday, any half-decent Toronto restaurant will be packed.

So if you walk in without a reservation, chances are you and your date are going to have to wait anywhere from 20 minutes to two hours for a table.

Making a reservation in advance will impress your date and save you a lot of time in the long run.

3. Don't talk too much about yourself!

People eating at a restaurant.

People eating at a restaurant.

Mariusz Szczawinski|Dreamstime

You're going on a date to get to know another person, not recite a sales pitch of why you're the perfect partner.

A conversation during a date should flow back and forth like a tennis match. You ask them a question, they ask you a question.

If you're monologuing, you're doing something wrong.

Be thoughtful and try to ask your date sincere, open-ended questions that help you learn about them.

If you're on a date with a tennis player, ask them how they got into the sport and why they pursued it! Listen while they're talking and ask a relevant follow-up question.

The secret to being a good date is active listening and timely questions.

I once had a date with a guy who spent about 30 minutes detailing how he hired a professional photographer to take his Hinge pictures to optimize likes, and I remember floating into the recesses of my mind and asking what karmic crime I had committed in a past life to end up here.

Don't be that person.

4. Don't order something you can't eat

Toronto is full of amazing food, but hey, sometimes we're not all pros at every cuisine.

So if you can't handle spicy foods very well, don't order a spicy dish that will have you grimacing through dinner and ordering glasses of milk by the dozen. Or a messy rack of ribs that will ruin your shirt and douse your hands in the sauce.

Order something you're comfortable eating and can snack on while making conversation throughout your meal.

5. Don't just pick a random restaurant or activity

Ask your date what type of food they like or what they like to do.

Before you broach the "where should we go" topic, ask the person you're seeing their favourite types of food and activities and cater your options towards things you'll both enjoy.

If they love golfing maybe mini putt would be a hit! If they love pasta more than their own flesh and blood, take them to Oretta or Trattoria Nervosa.

You don't want to pick a seafood restaurant only to find out later that they have an allergy to 90% of the menu... trust me.

6. Don't spend a fortune on a first date

A first date doesn't need to break the bank. It just has to be thoughtful.

Pick a restaurant or activity that's within your budget. You don't need to splurge just to make a romantic splash.

If money's a little tight, plan a date that will excite your partner based on their interests that's more affordable. If they love movies, take them to one of Toronto's free outdoor movies.

Pack a basket with comfy blankets, pillows and their favourite snacks and drinks. If you don't know what they like, ask them and then surprise them!

They'll be touched you remembered, and it will be just as special as dropping $200 on dinner and cocktails.

7. Don't be weird with the bill

A bill on a table.

bill on a table.

Trong Nguyen|Dreamstime

If you're a guy, you should pay the bill on a first date.

Everyone has their own opinion on who should pay the bill, but we can all agree there's nothing more painful on a date than a long pause after the bill hits the table.

The etiquette rule of thumb is that whoever asked the other person on the date should pay, and while splitting is an option, it's woefully unromantic, in my opinion.

Whenever I've been on a date, I'm always prepared to pay the whole bill, and I'll always offer to cover the check, but when my date fights me on it, I appreciate it.

I'm much more likely to go out with someone who effortlessly grabs the bill without making a fuss and politely declines my financial advances than someone who asks to split.

That being said, you should always offer to pay, it's just good manners, and if someone grabs the check the first time, make sure you grab it the next time regardless of your gender.

8. Don't ask if you can kiss your date

Consent is so sexy and so important!

But at the end of a first date, look toward your date's body language rather than asking outright if you can kiss them.

Are they lingering outside of the restaurant or their front door? Are they leaning in? Are you making prolonged eye contact without talking? Did they initiate a long hug while saying goodbye?

Don't just attack your date with your mouth but make sure you're relying on physical cues just as much as verbal ones.

Feel out the vibes before making your move, and go slowly. If their body language and the vibe feel promising, but you're still unsure, then you could slip in an "I'd really like to kiss you," but don't ask unprompted.

9. Don't play it cool after the date

You like them!!!

You have a big fat crush, and there's a hummingbird in your chest beating its little wings around your ribs!

If you have a great date, don't play it cool and wait three days to text.

At the end of the date, either in person or over text, tell your date you had a great time and that you'd love to see them again.

If they also had a great time, don't delay and get your second date in the books!

The best piece of advice I can give you is to be yourself.

You are wonderfully unique and you may have to kiss a couple of Canadian geese to find your perfect match but you'll find them.

Just stay hopeful and if it's not a match made in heaven, at least you've made a new friend in the city!

This article's right-hand cover image was used for illustrative purposes only.

The opinions expressed in this article are the author's own and do not necessarily reflect the views of Narcity Media.

Cheaper Than Therapy is a spicy column and video series hosted by Brooke Houghton where readers can share their own anonymous questions and get expert advice for free. Brooke speaks from her own experiences as a single 20-something woman in Toronto and brings on expert guests from therapists to celebrities to help solve your relationship, sex and love issues. So if you can't afford therapy from an actual professional, ask her a question here and tune in next month for another episode of Cheaper Than Therapy

Brooke Houghton
Brooke Houghton is a contributing writer for Narcity Media based in Toronto, Ontario.