FLIRTING CRUSH

How to not be weird when texting a girl for the first time

start a conversation

So, you’ve got her number. Nice. That’s step one. Step two? Figuring out how to text her without sounding like a robot or a guy who’s been reading too many pick-up artist blogs. Honestly, starting a conversation over text with a girl doesn’t need to feel like you’re defusing a bomb. But it can go sideways pretty fast if you're not careful.

We surveyed 183 women between the ages of 18 and 35 to ask what kinds of texts make them want to reply—and which ones make them throw their phone across the room (figuratively, we hope). Add in a few psychologist quotes and some painfully honest anecdotes, and boom: You’ve got a real guide, not just recycled advice from 2012.

Don’t say “hey.” Seriously. Just don’t.

We need to talk about this. The number of people who think “hey” is a valid opener is… concerning. In our survey, only 4% of women said they’d feel excited to get a “hey” from a guy they don’t know that well. You know what the rest said? That it made them feel like they were about to be bored.

“It signals zero effort,” said Dr. Mallory Kent, a psychologist who studies communication. “It’s the kind of message that puts all the pressure on the other person to make things interesting.”

Imagine someone walking up to you and just saying, “Hey,” and then staring at you like it’s your move. Weird, right? Same deal here.

Ask something—anything—specific

If you want to avoid the “hey” trap, start by asking a question. And not something creepy or weirdly deep, like “what’s your biggest fear?” Save that for, I don’t know, your third wedding anniversary.

If you met at a party, maybe: “Hey, did you ever end up getting that slice of pizza you were looking for?”

If you both like music: “Just heard a song I think you’d love. You into throwback R&B?”

The point is, a question gives her something to respond to. It’s like handing her a ping pong paddle instead of just serving and walking away.

Don’t try too hard to be funny—but also, be a little funny

Look, being funny over text is hard. Without tone or facial expressions, sarcasm can crash and burn. But a little light humor? It works.

One guy in our survey said he texted a girl, “If I had a dollar for every time I reread this message to make sure it didn’t sound creepy, I’d be able to afford therapy.”

She laughed. They’re dating now.

“It’s okay to be a little awkward,” says Dr. Kent. “Most people appreciate someone who doesn’t take themselves too seriously.”

Read the room (or in this case, the screen)

One underrated skill in texting is knowing when to stop. If she responds with three words and doesn’t ask anything back? She might not be that into it. Doesn’t mean she hates you. Maybe she’s busy. Maybe she’s just not sure yet. But if the energy is clearly low, give it a beat.

And for the love of all things decent, don’t text again 10 minutes later saying, “Did I say something wrong?”

Just… don’t.

Avoid weird compliments

Compliments are tricky over text. In person, tone helps. Over text? It can get cringey fast. Telling someone “you’re stunning” out of the blue, especially early on, feels a bit much. You might think you’re being romantic, but it often reads as too intense.

A better move? Compliment something specific and low-key. Like: “You’ve got a cool sense of humor. That joke about your boss and the parrot? Still laughing.”

It’s less about how she looks and more about who she is. Way more effective.

Use emojis… sparingly

Emojis can help lighten the tone. A well-placed ???? or ???? can make your message feel more relaxed. But don’t go emoji wild. This is texting, not a kindergarten sticker chart.

Also, and this was weirdly unanimous—don’t use the ???? emoji unless you already have that kind of vibe going. One woman said, “He sent a kissy face after I replied to his first message with ‘lol.’ I blocked him.”

So yeah. Be chill.

If you’re texting her, text her

This sounds dumb, but hear me out. Texting isn’t about just filling time. It’s about showing interest. If you send her a message, actually have something to say.

One survey respondent said, “He sent me ‘what’s up’ four times in a week with nothing else. I finally replied, ‘Not much, apparently.’”

And that was the end of that.

Timing matters, but not as much as people think

You don’t need to wait exactly 17 minutes to text her back so you seem cool. That’s high school nonsense. Still, if you text her at 2:03 a.m. on a Tuesday and you’re not both working night shifts, don’t be surprised if she finds it a little… odd.

Best window? Evening. People are winding down, phone in hand. Just don’t start texting like you’ve been holding in all your thoughts since lunch. A message or two to start is fine.

Know when to switch it up

If you’ve had a good back-and-forth over text, you can eventually switch to voice notes or suggest a casual phone call. Don’t do this immediately, though. And definitely don’t send a voice note out of nowhere saying “just thought you’d like to hear my voice.” That’s straight-up villain behavior.

One guy in the survey said he waited until they’d texted a few times, then asked, “Wanna call for five minutes? I have a terrible story I can’t type out.” She said yes. It worked.

So what’s the takeaway?

Text her like a human being. Be curious, not creepy. Ask real questions. Pay attention to how she responds. If it feels awkward, that’s okay. Everyone’s a little awkward. Just don’t pretend to be someone you’re not, and don’t force it.

Oh—and retire the “hey” forever. Please.

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