Honestly, we’ve all been there. It’s weird how your brain just goes blank when you’re around someone you actually like. Like, you’ve had conversations your whole life—why is this suddenly rocket science?
To help you out (and save you from more awkward weather chats), I asked 300 people between ages 18–30 about what actually works when it comes to keeping a convo going with your crush. The good news? You don’t need deep questions or dramatic icebreakers. You just need stuff that sounds like you.
Ask about their weird habits
This one surprised me, but it came up over and over in my survey. People love sharing their strange little routines—like needing the fan on to sleep, or eating fries with honey, or refusing to wear socks that don’t match.
“I told my crush that I name all my houseplants like they’re coworkers,” said one person. “Instead of thinking I was a weirdo, he said, ‘Wait, same,’ and we ended up sending each other plant updates.”
According to relationship therapist Maya Jin, sharing quirks is a low-stress way to connect. “It invites humor and makes the conversation feel personal without being too intense,” she explains. “And when someone laughs with you instead of at you, that’s chemistry right there.”
Talk about what you were like as a kid
This one’s gold. Not only does it make people smile, but it tells you a lot about their personality. Were they the class clown? The quiet observer? The bossy oldest sibling?
You can start light: “I used to wear a cape to school and thought I was a magician.” That’s not just funny—it makes you real. And it gives them something to bounce off of.
One girl told me, “I said I once ran away from home at age six because I didn’t want to eat green beans. He laughed and told me he did the same thing over a math worksheet.”
See? That’s bonding. That’s how sitcoms start.
Ask about their comfort shows, not just ‘What are you watching?’
Everybody asks, “What are you watching right now?” but here’s a better one: “What’s your comfort show when you feel like crap?”
Why? Because it skips the trendy stuff and gets into personal territory. There’s a reason someone watches The Office for the 18th time instead of trying something new. It tells you how they soothe themselves, what they think is funny, and what kind of vibe they go for.
“Talking about comfort shows works because it blends nostalgia, humor, and personality,” says Dr. Jamie Torres, who researches connection in early dating. “It tells you how someone deals with stress—and that’s more useful than knowing their top 10 Spotify tracks.”
(But yeah, music is good too.)
Talk about unpopular opinions, as long as they’re not too spicy
Hot takes can actually be kind of bonding—if you keep them playful. “Pineapple on pizza should be illegal” or “Summer is actually the worst season” are great starters. They’re low stakes, but fun.
One person in my survey said their first real laugh with their crush came after he declared that flip-flops were “a crime against footwear.” They ended up joking about weird fashion choices for 20 minutes.
Just don’t go into politics unless you really know your audience. You’re trying to flirt, not launch into a TED Talk.
Get weirdly specific with questions
Instead of “Do you like to travel?” (which everyone answers with a half-shrug), go for stuff like:
- “If someone gave you $1,000 and said you had to spend it in 24 hours, what would you do?”
- “What’s one food you irrationally hate?”
- “If you could be any minor background character in a movie, who would you be?”
These are weirdly fun, and the bonus is that you get way more interesting answers than the usual script.
According to Dr. Torres, “Specific questions require people to think creatively, which lights up more of the brain’s reward center. It’s science—but also just more fun.”
Talk about your ‘flop era’
You know, that period where nothing was going right and you were a bit of a mess? Maybe you had a haircut that aged like milk. Maybe you thought cargo pants were the moment. Maybe you joined a pyramid scheme. It happens.
Mentioning your flop era shows that you don’t take yourself too seriously. “Self-deprecating humor—when done in moderation—can be attractive because it feels real,” says Jin. “It shows that you’re okay with imperfection.”
One girl told me she shared her high school poetry with her crush. “It was terrible,” she said. “But he read it and said, ‘Honestly, you committed to the bit. That’s impressive.’”
Now they send each other old Facebook posts as jokes. That’s how real friendships—and sometimes relationships—start.
What to skip (unless you want to kill the vibe)
- Too many deep questions too fast. Save the “What are your greatest fears in life?” for later, not over coffee number one.
- Interrogation mode. If the convo feels like a job interview, take a breath. Ask, then actually listen.
- Oversharing about exes. No one needs to hear about your three-year situationship with someone who “didn’t believe in labels.”
Talking to your crush shouldn’t feel like defusing a bomb
It’s just a conversation. It can be weird, funny, awkward, or surprisingly sweet—and it’s all part of the charm. The goal isn’t to impress them with perfect answers. It’s to show up as yourself and see if something clicks.Because if it does? You’ll barely remember what you talked about. You’ll just remember how it felt.
Need help coming up with an opener that doesn't feel cringey?