WOMEN ARE COMPLICATED. I can say that because I am one.
We yearn for quintessential meet-cutes. We dress up for a Trader Joe’s run just in case the love of our life is reaching for the same ravioli. Wee theoretically love the idea of meeting someone in the real world—but the moment we get approached IRL, we run away at lightning speed. It begs the question: Is there a right way to chat up a woman in public without scaring her off? Or are dating apps and DMs our future?
As a romance-obsessed girlie, I’m not ready to resign myself to a world where my future husband’s first move is liking my Instagram story. So, I went on a mission to get intel from women on the best, non-creepy ways they’ve been approached offline. Armed with their testimonials and expert advice from dating coach Blaine Anderson, I’ve got you covered with concrete tips to master the art of a public pick-up.
Tip #1: Eye contact is everything.
If you spot someone who strikes your fancy but aren’t sure if you should advance towards them, follow Anderson’s first rule of thumb: “Always use eye contact as a cue to approach.”
To see this in action, I spoke with Miriam, a 24-year-old pre-med student who recently exchanged numbers with a biker at a crosswalk. “I was crossing the street, and I smiled at a cute guy while he was at the stoplight on a bike. About two minutes later, he biked up to me, introduced himself, and eventually asked me to dinner.” She credits their meet-cute to that initial smile they exchanged, revealing that eye contact or a friendly nod is her go-to move for signaling that she’s interested.
So, you’ve locked eyes. What next?
“Don’t overthink it,” Anderson advises. “Walk up, and say, ‘We made eye contact, and I wanted to introduce myself.’ Let conversation flow from there.”
Tip #2: Find common ground.
According to our expert, if you want to get the highest success rate when approaching someone IRL, “The key is to not ‘hit on’ girls, and to instead focus on creating warm and authentic interactions.” One sure fire way to do so is by leaning into commonalities.
I met Ryan in Washington Square Park, which was coincidentally the scene of her favorite meet-cute. She was cozied up on the grass in a cool leather jacket, when a male admirer approached to compliment the piece and ask where it was from. When she revealed that it was thrifted (the biggest flex, IMO), they instantly connected on their love for sourcing one-of-a-kind items.
“He asked if he could sit down, we got to talking about fashion, and then it segued into him asking if he could show me some thrift and vintage stores,” Ryan said. The pair ended up thrifting together multiple times, and while the romance was cut short, she recalls their meeting as “a very positive experience.”
What Ryan’s suitor did so well is that he discovered a topic they could bond over, one that even led to a potential date activity. When meeting someone new, it’s easy for the conversation to fall flat. Lead with subjects that the two of you can yap passionately about, and you’ll be golden.
Tip #3: Open with a genuine, non-superficial compliment.
While the women I interviewed differed on some fronts, they all aligned on one, very specific request: Don’t call them beautiful.
A compliment on one’s looks can be flattering, but it can also make women feel objectified and suspicious of your intentions. If you do want to open with a compliment, look for something more specific that isn’t based on her physical appearance.
Take Elana, a twenty-three-year-old fitness enthusiast who’s experienced her fair share of come-ons at the gym. But what separates the gentleman from the creeps is how, and what, they compliment. “I had a guy come up to me at the gym, and he just said, ‘I see you here all the time. You’re so strong. What’s your name?’” While this may seem like a simple approach, it hit all the right marks. “It’s so empowering, because he’s complimenting something about me, my strength, which to me is really sexy.”
For Sedona, an ultra-cool R&B musician, her favorite compliment came in a different form. “I was at the corner store looking so gross, but I had on this really cool sweater that my friend airbrushed for me,” she told me. “This dude came up to me, and instead of automatically flirting with me, he said, ‘Yo, I fuck with that sweater.’”
As an artist and creative, Sedona uses style to represent herself. The fact that someone was able to pick-up on that and use it to initiate a conversation was a huge green flag. “I was more open to talking to him,” she explained, “because I’m always down to talk about my style and wardrobe. That’s something that’s part of my identity.”
What did we learn, class? Instead of generic, superficial compliments, focus on something about the girl — her energy, her fashion sense, her strength — and comment on that. Not only will she appreciate it more, but a genuine conversation is more likely to follow.
Tip #4: Keep it low pressure.
There are two people in this world I’m more jealous of than anything: The first is Taylor Swift’s childhood bestie, Abigail Anderson. The second is Sarah, a 26-year-old who met her fiancé in the frozen aisle of Trader Joe’s. She was making her own Sophie’s choice (trying to decide on a TJ’s ice cream flavor) when someone appeared in her view and stuck out a pint, saying “You should get this one. It’s insanely good.” A little grocery store banter and a few years later, the couple is now ten months away from saying “I do.”
Not only did her future husband nail the opening line, Sarah loved how lighthearted and low pressure he kept their initial interaction. “He ended up giving me his phone number, which made me feel like I could decide whether or not to text him,” she explained. “I texted him right away, but I think that was just something that put me at ease.”
In dating coach Anderson’s book, this interaction would get five stars all around. By offering out his own number, Sarah’s hubby was keeping the stakes low — the key to success. “The less you invest in the outcome of the interaction and the more you focus on getting to know her, the more likely you are to land dates,” Anderson said.
Tip #5: Remember: Women want to be approached.
Despite the very mixed signals we can sometimes be guilty of, I promise you, women want you to be forward. Don’t believe me? Listen to Anderson: “I informally surveyed 13,000 single women in the U.S. and U.K. via Instagram earlier this year, and literally 95% said they wish they were approached by men more often.”
I recognize that there is a fear about coming across as “too forward” or “creepy,” but trust me, as long as you’re respectful, keep the conversation light, and bow out if the vibes are off, then you’ve got nothing to be afraid of. In fact, you might even make someone’s day.
And if you see me all dolled up at Trader Joe’s, do me a favor and help me pick out my next pint of ice cream.
