I Asked 50 Strangers the Best and Worst Dating Advice They’ve Ever Gotten—Here’s What They Said

Apr 14, 2025

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Hannah Feminella

In the spirit of curiosity (and chaos), I walked around New York with a mic and a mission: Ask 50 complete strangers for the best—and worst—dating advice they’ve ever received.
The answers? Chaotic. Enlightening. Occasionally unhinged. And honestly, wildly relatable.

So, grab a glass of wine and settle in for the advice that had me cackling, cooing and cringing in public like a woman with nothing left to lose…


The Actually Good Advice

  • “If you wouldn’t take advice from them on your career, don’t take advice from them on your love life.”
    She wins. End of post.

  • “Ask yourself: Do I like them? Not just: Do they like me?”
    A reminder that being chosen isn’t the same as choosing someone. Revolutionary.

  • “Date someone who makes your nervous system feel safe.”
    It’s giving regulated attachment style. We love to see it.

  • “The right person won’t make you overthink.”
    They’ll make you overeat tacos, maybe. But not overthink.

  • “Don’t confuse chemistry with compatibility.”
    Just because the sex is good doesn’t mean the relationship is.

  • “If they wanted to, they would. And if they wanted to but couldn't, they’d still communicate that.”
    Petition to get this tattooed across the city.


The Unhinged (and Occasionally Horrifying) Advice

  • “If he’s rude to you, he probably likes you.”
    ...said the patriarchy in 6th grade and never updated the software.

  • “Make him jealous. It keeps him interested.”
    That’s not a relationship, babe—that’s emotional CrossFit.

  • “Play hard to get. Always.”
    Or—and hear me out—you could just be emotionally available and save everyone the confusion?

  • “Don’t text back for three days.”
    Okay ghost of 2012, time to go back in the vault.

  • “Only date someone if they’re a 10 in ambition, looks, and income.”
    So…date a hologram?


The Advice That Was So Bad It Became Funny

  • “You have to let him think he’s smarter than you.”
    From the mouth of a great-aunt who thinks feminism is a TikTok trend.

  • “Never be the first to say I love you. That’s desperate.”
    Tell that to my best friends boyfriend of 3 years who snagged him with an “I love you” 3 months in and a cheese board.

  • “Keep a toothbrush at their place after the second date. Mark your territory.”
    This woman might be a genius or a sociopath. TBD.

  • “Date someone uglier than you. They’ll treat you better.”
    She said this unironically. I blacked out.


And the Collective Crowd Favorite...

“Date someone who feels like peace, not like a project.”
Everyone clapped. A couple cried. I almost proposed.


So, what’s the takeaway?

Well, aside from “never take advice from a guy in a fedora,” the real lesson is this: There is no one-size-fits-all in dating.
But if the advice you’re following makes you feel small, confused, or like you’re in a constant episode of The Bachelor—maybe it’s time to change the game.

Because the best dating advice I can give you?
Stop waiting for connection to magically happen in a sea of swipes and half-hearted chats.
Get clear. Get intentional. Get offline. Go on the date. In real life. With someone who actually wants to meet you. FROM will even help you make it happen- you know where to find us..


Until next time—may your dating advice be solid, your drink orders hot, and your exes watching from the sidelines x