Flirty questions to ask over text, and what to do with the answers.

"What's something you're weirdly competitive about?" is the best flirty question we know. Everyone has an answer that isn't embarrassing, and whatever they say, you now get to tease them about it for the rest of the week.

That's most of what makes a question flirty. It doesn't have to be about attraction at all. It needs a small stake and an answer you can play with. The questions below are sorted roughly by how far into a chat you'd want to be before sending them. All of them are PG-13, because the explicit stuff isn't flirting over text so much as skipping it, and it tends to land badly with people you've been talking to for two days.

Easy ones, for early on

These work in the first few days, when you know their name, their job and not much else.

• What's your most controversial food opinion?
• What would your friends say is your worst habit?
• What were you like at 15? Be honest.
• Which film have you seen more times than you'd admit to?
• What's your karaoke song, and how bad is it on a scale of one to the neighbours complaining?
• Coffee order. I'm judging.
• What's the last thing that made you laugh out loud on public transport?
• What's the most useless skill you have?
• What's a small thing that reliably makes your day better?

The coffee one sounds like nothing. It isn't. People have strong feelings about oat milk, and anyone who says "instant, three spoons" has handed you a whole conversation.

Would-you-rathers and quick picks

These are fast, there's no wrong answer, and every answer is something you can argue with. They also work well when a chat has gone a bit flat.

• Museum date or bowling?
• Would you rather plan the date or be surprised?
• Early breakfast or chips at midnight?
• Would you rather I sent a voice note or a long text?
• Dance badly in public or sing badly in public?
• Beach holiday or a city you have to walk 20,000 steps a day in?
• Would you rather win an argument or be right? (These are different, and how they answer tells you a lot.)
• Board games: fun or a threat to the relationship?

Pick one and commit to your own answer before they reply. "Bowling. I'm terrible and I'm loud about it" gives them something to tease you with too.

A bit bolder (still PG-13)

Save these for when it's already going well and they've been flirting back. If you're not sure they have, you're probably not there yet, and that's fine.

• What's the first thing you noticed about me?
• Be honest, how long did you spend on your reply to my first message?
• If we were out right now, where would we be?
• What's something you've always wanted to do on a date and never have?
• What would make a first date go well, in your book?
• Have you been smiling at your phone, or is that just me?
• Rate my texting out of ten. Be kind.
• What's the best compliment you've ever been paid? I'm taking notes.

The "where would we be" one is a team favourite because it's a plan in disguise. If they come back with the name of an actual bar and what they'd order there, that's not really a hypothetical any more.

The answer is where the flirting happens

A question on its own is just an opening. The flirting happens in what you do next, which is usually some mix of teasing them about the answer and giving your own, ideally built around the one detail that was funnier than the rest of it, because that's the bit they were secretly hoping you'd pick up on. Fire question after question and it turns into a survey. One good question, then five or six messages playing with the answer, is roughly the right ratio.

Here's the sort of thing we mean, with one of the Itclickt companions:

She answered, then left a loose end hanging for you to pull. Now there's a rivalry to ask about, and a man in a red hat you'll be hearing about for weeks. A good answer usually comes with a thread like that, and the flirting is mostly in noticing it.

If you want to try a few of these out before you use them on someone whose opinion you care about, companions are a decent place to do it. They answer in character, they tease you back, and some of them will make it clear they'd rather just be friends. Which is useful, in its way: a good flirty question should still work as a friendly one if the other person isn't interested. "What's your karaoke song" is fun either way. "What are you wearing" isn't.

A few to skip

"Why are you single?" sounds curious and lands like an accusation. There's no good answer to it, only defensive ones.

"What's your type?" puts them in the position of describing someone who might not be you. Ask what they noticed about you instead.

"What do you do for fun?" is fine, but it's a job interview question in a nicer jumper. "What did you do last Saturday?" gets you the same information with actual details in it, and details are what you can tease.

"Are you always this cute, or is it just today?" is a line with a question mark on the end, and they'll know.

And "you up?" at 1.17am has never, in the history of phones, been answered well.