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These children of Jewish mobsters were kept well shielded from their fathers’ affairs

Lisa Novick Greenberg/John Novick

By BERNIE BELLAN
What’s it like growing up the child of a mobster – and a Jewish mobster to boot?
The idea of stringing together various stories about children of Jewish mobsters came to me as I started to read a terrific new book that was sent to our office, totally unexpectedly.

The title of the book is “The Apple and the Shady Tree”. The author is someone by the name of Lisa Novick Goldberg. The book is available on Amazon in either paperback or Kindle format.
There were a couple of ideas that kept crossing my mind as I read Lisa Novick Goldberg’s book. One was: Are criminals self-isolating during these extraordinary times? After all, they don’t adhere to society’s norms at the best of times. Why would they lower themselves to start following the same rules that should apply to everyone else? What would someone whose livelihood depends on providing others with something that’s illegal to begin with – such as drugs or other contraband, gambling, and prostitution, do when most of us are told to self-isolate?
I worry for those types of people. It must be even more difficult for them to get by than it is for the rest of us. Think Tony Soprano and his psychiatrist.

Secondly, as soon as I started to read this book, I thought to myself: We’ve had stories that are similar in nature written about in the pages of this paper before. In 2014 I wrote a review of a book titled “Davey the Punk”, which was written by a well-known Canadian musician by the name of Bob Bossin – whose father was Dave Bossin (or “Davey the Punk” as he was known to all his friends).
In 2017 Martin Zeilig wrote a fascinating story for us about someone named Al Smiley, who was best friends with Ben “Bugsy” Siegel. Smiley was actually a former Winnipegger and Martin interviewed his daughter, whose name is Luellen Smiley.
As well, in 2015 CBC Radio ran an interview conducted by Anna Maria Tremonti with Sandra Lansky following the publication of Sandra’s memoir of growing up the daughter of Meyer Lansky, who was known as “the brains of the Mob”. Sandra Lansky’s book is titled “Daughter of the King: Growing up in Gangland”. I haven’t actually read that book, but I have listened to the interview a couple of times. It remains one of the greatest interviews I ever heard Anna Maria Tremonti do. (It ranks up there with Jian Ghomeshi’s interview with Billy Bob Thornton as one of the most riveting pieces of radio I’ve ever heard.)
As a matter of fact, I’ve urged the Jewish Heritage Centre of Western Canada to mount an exhibit on Jewish gangsters – in a departure from the standard custom of harkening back to a rose-coloured past that doesn’t shed much light on some of the more unsavoury aspects of Jewish life. Of course, if the JHCWC were actually to mount such an exhibit, whoever would be doing the research for it might not live long enough to see what comes of it.
I’ve also asked the organizers of Limmud whether I can present a talk at Limmud on Jewish mobsters – including many Russian oligarchs, but so far I haven’t been granted permission. Maybe next year I’ll be told to go ahead. There are a number of individuals I know who can provide me with first-hand information, some of whom are subscribers to this paper, yet whose identities must remain a secret.

But, to return to the original focus of this article: What’s it like to grow up the child of a gangster?
Here’s what Luellen Smiley, Bob Bossin, and Lisa Novick Goldberg had to say, in part:

Al Smiley/Luellen Smiley

From Martin Zeilig’s interview with Luellen Smiley: “Some children are silenced. The pretense is protection against people and events more powerful than them. As the daughter of Allen Smiley, associate and friend to Benjamin ‘Bugsy’ Siegel, I was raised in a family of secrets…
“When I was exposed to the truth by way of a book, I kept the secret, too. I was 13. My parents divorced, and five years later, my mother died. In 1966, I went to live with my father in Hollywood. I was forbidden to talk about our life: ‘Don’t discuss our family business with anyone, and listen very carefully to what I say from now on!’ But one night, he asked me to come into his room and he told me the story of the night Ben was murdered…
“After my father died, I remained silent, to avoid shame, embarrassment and questions. But 10 years later, in 1994, when I turned 40, I cracked the silence. I read every book in print – and out of print – about the Mafia. Allen Smiley was in dozens. He was a Russian Jew, a criminal, Bugsy’s right-hand man, a dope peddler, pimp, a racetrack tout. I held close the memory of a benevolent father, wise counselor, and a man who worshipped me.
“I made a Freedom of Information Act request and obtained his government files. The Immigration and Naturalization Service claimed he was one of the most dangerous criminals in the country. They said he was Benjamin Siegel’s assistant. They said he was poised to take over the rackets in Los Angeles. He didn’t; he sold out his interest in the Flamingo, and he went to Houston to strike oil…
“It seems there is no end to the stories surrounding Ben and Al. I am not looking for closure. I’ve become too attached to the story. To me, he was a benevolent father, a wise counsellor and a man who worshipped me.”

Bob Bossin in front of a family picture, including his father, “Davey the Punk”

Here’s an excerpt from my review of “Davey the Punk”, about Bob Bossin’s father, Dave Bossin: “As well – as he explains during the course of the book, he had to piece together his father’s past – which was kept well-hidden from him as he was growing up, and which largely remained a mystery to him until he was well into his 40s, through a series of interviews he conducted with relatives, friends of his father, and other individuals who happened to have dealings with Davey.”

Finally, we have Lisa Novick Goldberg’s memoir of growing up in a Mob-connected household with her father, whose name was John (or, as he was known to his friends, “Jonny”) Novick. Actually, his real name was “Herbert”, Lisa explains, but his Italian gangster friends thought that Herbert wasn’t the kind of name that a gangster should have, so they told him to change it to Jonny. In another fun aside, Lisa says that her father’s mother couldn’t pronounce the name Herbert anyway; she always called him “Hoibert”! Now that wouldn’t have placed him in good stead with his mostly Italian underworld friends, would it have? Also, since almost every gangster mentioned in this book had a nickname (My favourite was “Johnny Eggs”, because his mother raised chickens on a farm), it’s hard not to look upon these guys –who would slit your throat without hesitation if need be, with a certain fondness.
As with Luellen Smiley and Bob Bossin, Lisa Novick claims she had no idea about her father’s sordid background when she was growing up. She does say that when he was home, which wasn’t very often, he was always on the phone – and she wondered what he was talking about, but you can hardly expect a kid to understand what it is that their father is doing to make a living when he takes great pains to keep it shrouded in mystery.
It wasn’t until Lisa was a young adult that she was able to learn the truth about her father. She was actually summoned to appear before a grand jury in New York when she was only 22 (in 1980). While she denied having any knowledge of her father’s connections to the Mafia (he was actually well connected to the Genovese family – one of the five “families” that make up New York’s Mafia underworld), Lisa admits that, by that time, she was pretty much aware that her father was immersed in a wide range of illegal activities.
John Novick’s ostensibly legitimate business was as the biggest supplier of soft pretzels in New York City, with all the major sports venues being his customers. As well, he had kiosks near subway stations throughout the city. Lisa gives quite a detailed explanation of how money is laundered through what appear to be legitimate businesses, yet in footnotes that she provides throughout the book, she explains that she had to research almost everything she describes by looking at FBI archives and court transcripts, as well as other books and articles about New York’s Mafia underworld.
Yet, even though Lisa did realize her father was earning his income illicitly – for the most part (she does relate a series of hilarious business ventures in which he was involved that all failed), she doesn’t judge him at all harshly. In fact, she admits that she was always much closer to her father than her mother, whom she describes as having a terrible temper and much less gregarious than her extremely popular father.
One other aspect of John Novick’s career as a criminal is that, unlike almost everyone of his Mafia cohorts, he was never indicted and never served any time in jail. Although he comes across as someone who succeeded in making money despite his own inability to properly organize his affairs, apparently he was so popular with almost everyone who was involved in illegal activities that he benefited from his close relationships to the point where he was able to count on the largesse of some of the most vicious criminals in New York City for over 50 years. He also had a fantastic ability to do complex math calculations quickly, which proved invaluable to him as a gambler, which was his favourite pastime.
John Novick died in 2014. He had a myriad of health conditions when he was admitted to hospital one year before his death, principle among them being severe obesity. He weighed over 300 pounds when he was first hospitalized but had shrunk to a mere 150 pounds by the time he died. Reading about his voracious eating habits is quite repelling, although fascinating at the same time. He could devour a four-pound lobster, followed by a streak drowning in butter, Lisa writes, topped off by everything that was on a dessert tray that was brought to his table.

But, what of these mobsters’ children’s connections to their Jewishness? In none of the three cases I’ve cited does being Jewish play much of a role in their childhoods, other than when it comes to food. Lisa Novick says that both her parents were not at all involved in Jewish life. They didn’t attend synagogue nor did they observe any of the Jewish holidays (although she does describe her father’s weird habit of fasting on Yom Kippur by staying in bed and doing nothing but watch television. That was his only nod to Jewish observance, she writes.)

Meyer Lansky/Sylvia Lansky

As far as Sylvia Lansky goes, by the way, considering that her father was probably the most famous Jewish mobster of all time, what I remember best about her interview with Anna Maria Tremonti were some of her anecdotes about meeting famous celebrities. She tells the story of encountering Frank Sinatra in a New York restaurant one time when she was a little girl. Sinatra came over to the table where she was seated with her mother and father, but he accidentally knocked over the ice bucket that held a bottle of champagne directly on to her lap.
Sylvia describes how a look of mortal fear came into Sinatra’s eyes; clearly he thought that Meyer Lansky might order a hit on him right then and there. When Anna Maria asked Sylvia how she felt at that moment, I’ll always remember her answer: “I was cold.”
Sylvia also relates her own torrid love affair with Dean Martin. He could make love six times in one night, she recalls during the interview. Jews and Italians – joined at the hip, and often other places as well.

So – these were all spoiled children of men who made their money illegally – and none of them wondered where all the money was coming from. Is that unusual? I’m not so sure.
It’s one thing to not know what your father does for a living, but it’s another thing to see your house fill up with material goods – as was the case with all four of these mobsters’ children. Wouldn’t you wonder how your father was able to acquire so much “stuff” – and why were all their fathers so secretive about what they did?
I’ve barely mentioned the mothers of the children who grew up with mobster fathers. I suppose one can make a “deal with the devil” fairly easily if need be. There’s a lesson in here somewhere about how people can rationalize their behaviour. Yet, I’m sure you’re just like me in agreeing that reading about the family lives of mobsters – just as it was depicted on “The Sopranos” is noteworthy not for its excitement, but for the extreme pains criminals take to keep their lives as mundane as yours or mine.

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Fake IDs and Underage Bettors: The Growing Problem for Sportsbooks

The​‍​‌‍​‍‌​‍​‌‍​‍‌ expansion of legalized sports betting worldwide has resulted in sportsbooks grappling with a problem that they can no longer overlook: the increase in underage individuals using counterfeit identification to place bets. As more and more ways to bet through mobile apps and online sign-ups emerge, minors who are set on their goal are inventing ways to get around age limits. The emergence of this trend is a breach of the law and morality; however, it is also an enormous problem that threatens the very existence of the platforms, which are forced to rigorously obey the regulations ​‍​‌‍​‍‌​‍​‌‍​‍‌.

Why Fake IDs Are Becoming More Sophisticated

Conventional​‍​‌‍​‍‌​‍​‌‍​‍‌ fakes used to be quite simple to recognize—low-quality printing, different fonts for the text, and inconsistent holograms would make them not very reliable for any kind of verification. But counterfeit documents have changed significantly over time. Nowadays, fakes are made better with the help of printing technology and software, and they can even copy barcodes and other scannable features, so their IDs look almost real.

This fact complicates things significantly for sportsbooks, especially those operating online. Most of the time, automated identity verification systems capture a user’s photo and perform basic data matching. In cases where a very good fake ID is used by a teenager who looks older, some systems cannot recognize the trick. Therefore, young bettors have found ways to be able to place wagers through these ​‍​‌‍​‍‌​‍​‌‍​‍‌loopholes.

The Influence of Social Pressure and Online Culture

Social​‍​‌‍​‍‌​‍​‌‍​‍‌ media is a major factor in the increase in risky behavior that minors are engaging in. On various platforms such as Instagram, TikTok, and Reddit, teenagers come across betting slips, parlay wins, and big-payout screenshots that are shared, most probably, by other users. The glamorization of sports betting is leading young people to copy the behavior of influencers, older friends, or even celebrities, as they think that it is the right thing to do.

The competitiveness usually associated with sports is one of the reasons some minors decide to bet on sports. For many, betting becomes another way to engage as a fan—by predicting outcomes, challenging friends, and experiencing the same excitement that adult fans enjoy. Unfortunately, only a small number of minors fully understand the financial risks involved, making them more vulnerable to developing harmful patterns that could continue into adulthood. This is why choosing the most responsible sportsbook, which you can discover more here, is essential. Such platforms provide guidance, enforce safe practices, and ensure regulated play, allowing fans to engage with sports betting in a more informed, secure, and controlled manner.

Sportsbooks Facing Regulatory Pressure

The​‍​‌‍​‍‌​‍​‌‍​‍‌ sportsbooks are being given the task of more closely monitoring and preventing minors from betting on their platforms. If they fail, harsh penalties are possible, including severe fines, loss of a gambling license, and negative publicity that undermines a brand’s trustworthiness. As a result, it is becoming increasingly difficult for people to verify their identities, although this also inconveniences those who are, in fact, legitimate users.

Sportsbooks have to decide between two options that are in conflict with each other: on the one hand, they have to keep the registration process as simple as possible, and on the other hand, they have to carry out age verification in a very thorough manner. The work of balancing is tough, and the underage gamblers are trying all methods to find a way ​‍​‌‍​‍‌​‍​‌‍​‍‌out.

The Rise of Identity Fraud Services

An alarming trend is the emergence of online vendors who openly advertise fake IDs and identity documents. These vendors often claim their products can pass standard sportsbook checks. Some even tailor IDs to specific regions, knowing that certain provinces, states, or countries use verification systems that rely heavily on image comparison rather than live validation.

The availability of these fraudulent services not only empowers minors but also exposes sportsbooks to risks related to stolen identities, money laundering flags, and fraudulent accounts that may later become legal liabilities.

The Consequences for Underage Bettors

While​‍​‌‍​‍‌​‍​‌‍​‍‌ a minor might think that gambling is just a bit of fun without any harm, the outcome can be quite serious. If there is a catching, accounts are closed right away, winnings are confiscated, and parents or guardians, in some cases, are made legally liable for any financial disagreements. Besides that, the risk of developing a gambling problem in the future increases with early exposure to gambling, especially since teenagers are more impulsive and less capable of handling financial risks.

The majority of minors are not aware that sportsbooks keep very detailed records of their activities, including device information and IP addresses. In case a fake ID works one time, using it multiple times will definitely lead to getting ​‍​‌‍​‍‌​‍​‌‍​‍‌caught.

A Growing Problem That Requires Joint Action

Fake​‍​‌‍​‍‌​‍​‌‍​‍‌ IDs and underage betting are issues that have become a major challenge in the industry, and no single stakeholder can solve these problems on their own. Sportsbooks need to enhance their identity verifications, regulators should get prepared for new types of fraud, technology providers have to come up with new solutions more quickly, and parents should always be aware of what their children are doing online. The industry’s rapid development is making this problem more and more urgent because the number of minors trying to get around the safety measures is increasing.

Sports betting can serve as a fun and legal form of entertainment for adults, but the need to protect the youth is what defines the industry and ensures its survival in the long run. As the quality of fake IDs keeps improving and the online culture is more and more inclined to consider betting as a normal activity, sportsbooks must ensure that underage users do not have access and that the environment is safe for all users. They need to do this now more than ​‍​‌‍​‍‌​‍​‌‍​‍‌ever.

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How Canadians Are Adapting to the Boom in Legal Sports Betting

Canada’s​‍​‌‍​‍‌​‍​‌‍​‍‌ fan engagement with sports has been radically changed by the recent single-event legalized sports betting. In the past, this was something you could only do through offshore sites or informal pools, but now it has become a normal part of the Canadian sports culture, according to GamblingNews.com. Online sportsbooks are being established at the provincial level, and private operators are entering the regulated markets, so Canadians are discovering new means to entertain, grasp, and make correct decisions in sports ​‍​‌‍​‍‌​‍​‌‍​‍‌betting.

Widespread Adoption Across Provinces

The implementation of legal sports betting has varied across Canada’s provinces, but uptake has been strong in all jurisdictions. With its liberal licensing regime, Ontario has emerged as the most lively market in the country, thus enabling a multitude of private sportsbooks to compete. In the rest of the provinces, there are mostly platform operators controlled by the government; however, users are still in a state of rapid adjustment to the broadened offerings and new ways of wagering. As accessibility gets better, Canadians are becoming more aware of the distinctions between markets, bonuses, and betting styles, which makes the transition seem more like a logical continuation of their current sports ​‍​‌‍​‍‌​‍​‌‍​‍‌habits.

Increased Engagement with Sports and Data

Legal​‍​‌‍​‍‌​‍​‌‍​‍‌ betting has had an influence on how sports are consumed by a lot of Canadians. Fans are following gambling news, analyzing games in detail, checking lines more carefully, following injuries, and using statistics to make the best decision. The game-day experience has been expanded by betting, which has thus motivated fans to retain basic team loyalty. The rise of data-driven content, such as odds breakdowns, predictive analytics, and expert commentary, has been instrumental in making sports more interactive. Rather than being a passive viewer, a Canadian is now engaging more with the numbers, trends, and probabilities, thereby deepening his/her understanding of the games.

Growth of Responsible Gambling Education

As​‍​‌‍​‍‌​‍​‌‍​‍‌ betting gets more and more exposure, a conversation about safe play is also getting louder. Gambling organizations in Canada have put in place a variety of measures and have devoted a lot of resources to making gambling more responsible and safer. Users have changed their behavior as well; they are now more aware of tools such as deposit limits, time monitoring, self-exclusion programs, and reality checks. Different provinces put a lot of effort into education first, thus helping bettors notice the signs of risky behaviour and learn how to stay within healthy boundaries. This cultural change is contributing to the normalization of responsible gambling practices instead of being treated as a mere ​‍​‌‍​‍‌​‍​‌‍​‍‌intervention.

The Social Element of Modern Betting

Since​‍​‌‍​‍‌​‍​‌‍​‍‌ the legalization of sports betting in Canada, it has become much more of a social activity. People in their friend circles now talk about their bets, share parlays, and watch matches together, thus creating a new level of fun. Social media is very much involved in it as bettors post their predictions, celebrate their wins, or explain their unfortunate outcomes. There are more and more online communities dedicated to betting discussions, where people find wagering as a mutually enjoyable pastime rather than a lonely one. The feeling of togetherness is what makes Canadians use betting as a part of their sports routine in a joyful and engaging ​‍​‌‍​‍‌​‍​‌‍​‍‌manner.

Adapting to the Variety of Betting Options

With​‍​‌‍​‍‌​‍​‌‍​‍‌ the legalization of sports betting in Canada, there are now more options available that go beyond the typical single-game bets. Live betting, player props, same-game parlays, and futures markets have all become elements of the modern betting landscape. Such a variety demands the adaptation of the bettors, and a considerable number of them are figuring out the operating principles of each type, the value of the times when they offer, and the manner in which odds change dynamically. In addition, bettors are becoming acquainted with such concepts as payout volatility, implied probability, and risk management. The learning curve is definitely there, but it has also resulted in a richer and more strategic betting ​‍​‌‍​‍‌​‍​‌‍​‍‌experience.

Integration of Betting in Sports Media

Wide​‍​‌‍​‍‌​‍​‌‍​‍‌ channels and sports networks in Canada have been very much on board with the advent of the betting boom. Playouts of betting lines are part of the pre-game shows, analysts are using betting language patently to highlight something on the field, and treat the sports betting companies as a partner to a team or a league for branded content. Canadians are warming up to the reality where the provision of betting information is just a normal part of their sports coverage. The change is considerable, and it can be seen as a transitory moment when betting moved from being a small niche topic to becoming a standard element of sports ​‍​‌‍​‍‌​‍​‌‍​‍‌entertainment.

A Growing but Responsible Cultural Shift

Canadians,​‍​‌‍​‍‌​‍​‌‍​‍‌ in the wake of legalization, see sports betting as one natural way to extend their love for sports while recognizing the necessity of self-control. Thanks to enhanced access, better education, and more transparent platforms, the whole betting experience has become safer, more enjoyable, and more a part of the daily sports culture. Canadians, as the market expands, are creating a scenario where gambling becomes a tool for deepening their connection with sports rather than a source of ​‍​‌‍​‍‌​‍​‌‍​‍‌anxiety.

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How to Start Dating Online in Canada, Especially Ontario



Online dating in Canada can be genuinely effective, but only if you approach it like a simple process instead of a high-stress hobby. Ontario is a good place to date online because the population density (especially around the GTA) creates more active pools, while smaller cities still have enough users if you set your filters intelligently.

This guide gives you a practical Ontario-focused playbook: how to start dating online, what to set up, how to message, how to move to an actual date, and how to protect your time and safety.

Quick-start plan for Ontario singles

StepWhat to doOntario-specific exampleCommon mistake to avoid
1. Pick your laneChoose 1–2 platforms based on your goalToronto: nearly any major app is active; smaller towns: broaden radius to nearby citiesDownloading 6 apps and burning out fast
2. Build a “real” profile4–6 photos + short bio + 2 promptsAdd a local hook: “Best coffee spot in Ottawa?” or “Best weekend day trip from the GTA?”Only selfies, no bio, or “ask me”
3. Message with intent1 specific question + 1 next step“Coffee or a walk this week?”“Hey” and waiting for magic
4. Move to a date quicklySuggest a public, simple meet“30–60 minutes at a cafe near Union Station”Texting for 3 weeks, never meeting
5. Use safety rulesPublic first date, own transport, tell a friendShare date location + time with a friendFirst meeting at someone’s home
6. Filter hard, stay kindEnd mismatches early and politely“I’m looking for something more serious—wishing you the best.”Debating obvious red flags

1) Choose apps based on what you want (not what’s trendy)

Before you pick anything, decide your “dating intention” for the next 30 days:

  • Serious relationship-focused: choose platforms where profiles have prompts, values, and more context. These tend to produce better conversations and clearer intentions.

  • Casual dating / exploring: faster, swipe-heavy apps can work if you’re direct and you don’t take it personally when people vanish.

  • International or broader discovery: consider platforms that make cross-border matching and messaging easy, especially if your local pool feels repetitive.


Ontario tip: if you’re outside Toronto or Ottawa, don’t assume “online dating doesn’t work.” Often it’s a settings problem. Increase your radius to include a nearby hub (for example, Hamilton, Kitchener-Waterloo, London, or the GTA), and be open to meeting halfway.

2) Build a profile that feels human (and gets better matches)

Your profile isn’t a résumé. It’s a conversation starter. The best profiles do two things:

  1. show what you look like, clearly

  2. show what it might feel like to date you


Photos: a simple set that works

Aim for 4–6 photos:

  • One clear face photo (good lighting, no sunglasses).

  • One full-body photo (normal setting, not a bathroom mirror).

  • One lifestyle photo (hobby, cooking, gym, hiking, reading, music).

  • One “social proof” photo (with friends is fine, but make it obvious who you are).

  • Optional: a photo that shows your vibe (casual, dressed up, outdoorsy, artsy).


Avoid extremes: all selfies, all group shots, all travel photos, or filters that change your face. You’re not advertising perfection. You’re signaling honesty.

Bio: a 3-line formula that converts

Use this structure:

  • Who you are: one sentence

  • What you want: one sentence

  • Local hook: one sentence


Example bios (Ontario-ready):

  • “Ontario-based, equal parts ambitious and laid-back. Looking for a real connection with someone emotionally mature. Tell me your go-to comfort food or your favorite hidden spot in your city.”

  • “New-ish to the area and building a life I’m proud of. I’m dating with intention, but I like things to unfold naturally. Coffee dates and good conversation beat endless texting.”

  • “I’m the type who plans a day trip and packs snacks. Looking for someone kind, consistent, and curious. Bonus points if you like markets, walks, and laughing at dumb jokes.”


3) Messaging that doesn’t sound like a bot

Most conversations die because people write low-effort openings. Your first message should be:

  • specific

  • easy to answer

  • slightly playful or warm

  • connected to their profile


Openers you can copy

  • “You seem like someone with good taste—what’s a perfect Saturday for you?”

  • “Quick question: coffee first date or a walk first date?”

  • “You mentioned hiking—are you more ‘short scenic trail’ or ‘full-day mission’?”

  • “What’s the most underrated place in your city for a chill date?”

  • “Two truths and a lie—go.”


A realistic mini-script to move toward a date

  • You: “I’m enjoying this chat. Want to keep it simple and do coffee this week?”

  • Them: “Sure.”

  • You: “Great. I’m free Thursday evening or Sunday afternoon. Which works?”


In Ontario, many people appreciate directness because schedules fill up quickly (commutes, hybrid work, family obligations). Clarity reads as confidence, not pressure.

4) First date ideas that work in Ontario year-round

Plan dates that survive weather and keep pressure low.

Best first-date formats:

  • coffee/tea (60 minutes is perfect)

  • casual lunch

  • market + snack

  • walk in a busy, public area (only if weather is decent)

  • museum/gallery (good for conversation breaks)


Ontario-specific practical tip: keep the first meet short and public. If it’s going well, you can extend it. If it’s not, you can leave politely without feeling trapped.

5) Safety and boundaries (the non-negotiables)

Online dating is normal. Basic safety habits should be normal too.

Do this every time:

  • meet in public for the first date

  • use your own transportation

  • tell a friend where you’re going and when you expect to be done

  • keep personal details (address, workplace specifics) private until trust is earned


Watch for pressure signals:

  • pushing to meet at their home immediately

  • refusing a simple video call but demanding quick trust

  • love-bombing (intense affection very early)

  • turning the conversation toward money, “business,” or investments


If someone reacts badly to your boundaries, that’s useful information. It means your boundaries are working.

6) Ontario realities: age and alcohol

If you’re dating in Ontario, it’s also helpful to know common legal basics: the age of majority is 18, and the legal drinking age is 19. If you’re unsure or you’re traveling within Canada, double-check local rules, but those are the typical Ontario standards people plan around (especially when choosing bars or venues).

7) A simple 2-week routine that prevents burnout

If you want progress without turning dating into a second job:

Week 1

  • build a solid profile (one evening)

  • swipe/message 15–20 minutes per day

  • aim for 5–10 quality conversations, not 100 matches

  • propose 1–2 simple dates


Week 2

  • go on those dates

  • adjust your profile based on who you actually liked

  • tighten filters (age range, distance, intentions) to reduce noise


Online dating improves fast when you treat it like an experiment: test, learn, refine. You don’t need more apps—you need better signals, clearer messaging, and consistent boundaries.

If you want, tell me your approximate age range and whether you’re aiming for serious, casual, or international dating, and I’ll tailor the examples (bio + openers + first-date ideas) specifically for Ontario in the same format.

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