
What to know
- Some residents swear by pickup lines (even claiming high success), while others find them awkward or creepy—preferring genuine conversation instead.
- According to a dating expert, flirting works best when it feels natural and respectful, with compliments focused on personality or energy rather than physical appearance.
- Pickup lines can fall flat on dating apps where tone is hard to read, while in real life, reading the room, timing your approach, and showing genuine interest make a bigger difference than any scripted line.
“Hey, wait—I’ve seen you before… in my dreams.” Are pickup lines still in, or is there a new playbook when it comes to flirting?
First impressions matter, so some Torontonians jump right in with a pickup line, but others are grossed out by them – wishing for more conversation, instead.
For this edition of This Is Dating Now, Now Toronto asked Torontonians how they flirt, and a dating expert weighs in.
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Here’s how Torontonians flirt
A Toronto resident, Messi, explained he uses his university major to rizz someone up. “Hey, I’ve seen you before. I think we have the same class.” That sparks conversation, to which the other person typically asks which class. “I’ll be like, I think we have chemistry,” Messi typically replies.
He said he has a 100 per cent success rate and women always give him their phone number to this pickup line.
Though Messi loves using pickup lines, he doesn’t wish for a woman to ever use one on him. “It would just feel kind of emasculating,” he explained.
Toronto resident Uma, however, felt pickup lines are outdated. “It would be nice for someone to just ask me how my evening’s going… Just be caring like we’re just having a conversation,” she said.
This comes after a multitude of pickup lines she’s experienced. Some include:
- “I feel very platonic about you, but I’d also be down to give you an orgasm.”
- “Hey, wait—I’ve seen you before… in my dreams.”
- “Are you from Tennessee, because you’re the only ten I see.”
She says all these lines made her feel disturbed. “I didn’t want that,” she added.
Thankfully, not all men use pickup lines. Torontonian Idris even said he finds them “disgusting,” telling men, “Go have a normal conversation like a normal human being, fellas.”
In contrast to Messi, he appreciates when someone approaches him. “I take it as a compliment… I respect the approach and the game. It takes a lot to appreciate someone and get out of your comfort zone,” he said.
For Toronto resident Alex, he charmed his way into getting a girlfriend. “She’s very intelligent, so I kind of used that for our conversation,” to which he spoke about history. Though he joked about what probably charmed her, “Realistically, it’s probably my accent,” as he’s half Italian and half English.
Using this technique has gotten him into a three-year relationship with her, going strong.
But for Torontonian Julian, he usually uses his body rather than words. “I tend to go to a lot of clubs, so it’s usually dance with them first, figure it out later… It’s easier to move with the body than just to speak.”
But he’s also been a victim of pickup lines. Someone has once told him, “Have you ever been arrested? Because, you know, it’s illegal to look that fine.” For Julian, though, all that matters is the delivery of it. “It was just like this really drunken, quiet, stuttering man. I was like, ‘Oh, this is not really doing it for me I fear.’”
So how should you flirt?
Toronto Dating Hub Founder and Dating Coach Andrea Lo touched on Julian’s experience, explaining that the idea of a compliment isn’t necessarily wrong, it’s often about execution.
“People often go for a compliment about their physical appearance. And to be honest, having talked to thousands of women that come through my events… women are like, ‘What, are we pieces of meat? It’s like, why are you commenting on my physique?’” Lo said.
Lo explained it feels like getting undressed by someone with just their eyes, and can feel insensitive and disrespectful.
Instead, she recommends complimenting someone’s smile or energy. “It takes us by surprise and it feels like you’re actually genuine and curious about us,” she said.
Lo shared that pickup lines can work – or can’t. “I think the big part is if they feel natural and genuine. I think authenticity matters.”
She explained that pickup lines can sometimes be used for “getting women into bed,” but it should instead be used with positive intentions. When done right and authentically, it has more chances of working.
Lo advised not to use ChatGPT or have something sound too rehearsed, it’s better when it’s natural.
But on dating apps, it’s harder to get a pickup line to work. “You can’t read energy through a text… [A pickup line can be] so surface level, it’s rinse and repeat. You could have copied and pasted it,” she said.
Lo suggests when using a dating app, to see someone’s profile and ask them a question or share a similar experience. For example, if there’s a picture of a sunset in Lisbon, to say you just came back from there and ask where they went. Or, if you haven’t travelled there, to ask where they went to because you’ve been wanting to go there.
In person or online, she suggests “vibe-checking yourself” so you’re not creepy at an event.
- How am I dressed?
- Am I charming?
- Am I socially awkward?
Essentially, self-evaluate and get some professional help and tips if you’re having trouble talking in a romantic setting.
Also, it’s important to understand cues. If someone you’re interested in is in a serious and deep conversation with their friends, don’t go up to them. “It doesn’t matter if you had the pickup line, it’s like dude, you didn’t read the room, now you’re not welcome,” Lo explained.
But if you choose the right time and your pickup line just doesn’t go quite as planned because you’re nervous, it’s okay to say you’ve screwed up because of your nerves and that you just wanted to talk to them – as long as it’s in an honest and authentic way.
Got a dating story for us? We want to hear it! Send your experiences to news@nowtoronto.com for a chance to be featured in a future edition of This Is Dating Now.
