How to Flirt (Even If You Think You Can't)

Entry No. 229 ·

In a busy bookshop café on a Saturday afternoon, a woman of about twenty-two in a plain oversized cardigan and a man of about twenty-three in a plain grey sweatshirt share a small table by the window, both mid-laugh at something she has just said, two half-finished coffees between them and a single deep rose pink tulip in a small glass; around them, other young customers read and chat, everyone in plain clothes with no lettering or logos.

By The IF Team

To flirt, let someone see that you are enjoying them a little more than you would enjoy a friend, and leave room for them to do the same. Hold their eye a beat longer, ask about the thing that makes them light up, tease gently, notice something specific about them, and then watch whether any of it comes back. Good flirting is playful rather than polished. It shows interest without demanding anything, and it stops the moment the other person is not playing. There is no single correct way to do it — there are styles, and the best one is the one that sounds like you.

If you are convinced you are hopeless at this, you are in large company, and you are probably wrong. Nobody is taught to flirt; most of us picked it up from films, friends and a few mortifying evenings. People also judge themselves harshly: in a series of studies, strangers who had just chatted consistently underestimated how much their conversation partner liked them. The version of you that feels awkward from the inside usually comes across as warmer than you think.

Flirting is also how most people test the water before saying anything outright. Sometimes the water is not yours to test: they are seeing someone, or you are, or the moment simply never arrives. That is where IF comes in. It is an app for saying how you feel, honestly, whether you are single or in a relationship and whoever has caught your eye — you take a feeling that has already grown in real life, put it into words in the app, and act on it when the time is right.

What flirting is, and what it is not

Flirting is a signal with a smile in it. It says “I like being around you” in a way that leaves both of you free to treat it as play. That freedom is the point. It lets two people find out whether the interest is mutual without either of them having to stake everything on a declaration.

It is not a set of lines, a performance or a technique for getting past someone’s reluctance. Anything that relies on pressure, persistence or making someone feel smaller is not flirting, however it is packaged. And it is not a promise: flirting with someone does not oblige either of you to take it further.

Find your flirting style

Researchers at the University of Kansas surveyed more than 5,000 adults about how they show romantic interest and found five broad flirting styles: traditional, physical, sincere, playful and polite. Most people use a blend, and none is the right one. Knowing which comes naturally to you means you can lean into it instead of copying someone else’s.

  • Sincere: you flirt by connecting. Real questions, real answers, and the feeling of being properly listened to. If deep conversations come easily to you, this is your strength.
  • Playful: you flirt for the fun of it. Banter, teasing and running jokes. It is lovely to be around, though it can be hard for the other person to tell when you mean it.
  • Physical: you flirt with your body as much as your words. Eye contact, closeness, turning towards someone. Powerful, and it needs the most attention to how the other person is responding.
  • Polite: you flirt carefully and by the rules. Respectful, unhurried and never pushy, which can mean your interest is easy to miss.
  • Traditional: you expect the familiar script, where one person makes the moves and the other responds. Comfortable for some people, though it can leave both of you waiting for the other to start.

In that research, the sincere, physical and playful styles went with more dating success, and the sincere and physical styles with relationships that grew quickly and felt emotionally close. Take that as encouragement to be warm and present, not as a rule. A polite flirt who is clearly enjoying someone beats a playful one who is performing.

How to flirt in person, step by step

  1. Start with warmth, not a line. A smile and a comment about something you are both looking at — the queue, the band, the dreadful quiz question — is all an opening needs.
  2. Ask, then ask again. A first question starts a conversation; a follow-up shows you were listening. In studies at Harvard, people who asked more questions, especially follow-up questions, were better liked by the people they were talking to.
  3. Make it specific. Notice something only they would say or do, and tell them. A specific remark proves attention in a way no compliment from a list can; there is more on how to compliment someone you like.
  4. Tease lightly, and only upwards. Gentle teasing about a harmless quirk is affectionate. Anything about their body, their background or something they cannot change is not.
  5. Let your body agree with your words. Face them, keep your phone away, hold eye contact a moment longer than usual and smile when you mean it.
  6. Leave on a high. End while it is going well, with a hint of a next time: “I want to hear the end of that story. Coffee next week?”

If they are someone you see often — a classmate, a teammate, a friend of a friend — it helps to be around before you try to be noticed; getting your crush to notice you covers that slower route.

Flirting by message and on the apps

Messages strip out your face and your voice, so the same playfulness has to travel in words: callbacks to earlier jokes, questions only they could answer, an emoji where you would have smiled. The danger is that a chat becomes a hobby rather than a bridge. Use messages to build the spark, then suggest meeting. How to flirt over text goes into the craft of it.

How to tell if they are flirting back

Flirting is a conversation, so pay as much attention to what comes back as to what you send. Encouraging signs include:

  • They match your energy: you tease, they tease back; you lean in, they do too.
  • They ask you questions, including follow-ups, rather than only answering yours.
  • They find reasons to extend the moment — another drink, the longer walk, the last conversation of the night.
  • They pick up threads later: a joke from last week, something you mentioned in passing.

None of these is proof. Plenty of warm people are like that with everyone, which is exactly why telling flirting from friendliness is so hard, and why the wider picture in the signs someone likes you matters more than any single moment. When you still cannot tell, the kindest move is to be a little clearer yourself.

When it is not returned

Sometimes the energy does not come back. Their answers get shorter, they turn to someone else, they mention plans that do not include you. That is an answer, and a graceful exit is the most attractive thing you can do with it. Smile, change the subject or wish them a good night, and do not try again harder in the same evening.

The same holds after a clear no. Flirting only works between two people who are both choosing it, so the moment someone stops choosing it, so do you. Being turned down is not a verdict on you. It is information, and it frees you to spend your charm on someone who wants it.

From flirting to something real

Flirting is a beginning, not a destination. Once the interest is plainly mutual, the next step is to say so in a way that cannot be mistaken for banter. That might mean asking them out with the word “date” in the sentence, so neither of you is left wondering whether it is a date or just hanging out. It might mean the moment at the end of the evening when you are both deciding whether to kiss — and asking is part of the flirting, not the end of it.

Whichever it is, clarity is kind. A good flirt makes the other person feel wanted and free at the same time.

Where IF fits: when flirting is not the honest option

Flirting works best when you are both free to play. When one of you is in a relationship, it gets complicated fast: what feels like harmless warmth to you can feel like a line crossed to someone else, and anything you would need to hide has already gone too far. Feelings across those lines are normal and nothing to be ashamed of; it is cheating, and the lying that comes with it, that does the damage.

IF gives that kind of feeling somewhere honest to go instead of a grey area. If the person you like is taken, or you are, you can write it plainly in an IF — up to 250 characters, sealed — rather than flirting around it. While either of you is with someone, IF will not let a chat start at all, so the message makes no demand on anyone in the meantime: it sits sealed until you are both single. Should they already be on IF, they might get a note that an IF is waiting — with no name attached and none of your words.

If you are both single, IF works like any dating app: send a Like, and if they Like you back, a chat opens. If they have not joined yet, you can address an IF to the email, number or Instagram handle they gave you themselves, and it will be there if they ever sign up. Your first IF is free. Flirting is the hint; an IF is the sentence you mean.

Questions people ask

What actually counts as flirting?

Anything that signals romantic interest playfully rather than outright: lingering eye contact, teasing, compliments with a bit of warmth in them, finding reasons to be near someone. What turns friendliness into flirting is usually intent, and the fact that you would behave a little differently with someone you were not drawn to.

Can you learn to flirt if you are shy?

Yes. Shy people often make excellent sincere flirts, because they listen well and ask real questions. Start small — one longer conversation, one specific compliment — and let warmth do the work that confidence does for other people. Flirting is a skill, and skills improve with low-stakes practice.

Is it okay to flirt when you are in a relationship?

Couples draw that line differently: some are relaxed about light, friendly flirting, others are not, and it is worth knowing where yours sits. If it is a real crush, though, flirting tends to blur things. An IF holds the feeling honestly instead, and nothing opens until you are both single; there is more on having a crush while you are in a relationship.

How do you flirt without being creepy?

Pay attention to the other person more than to your own performance. Keep it light, keep it public, notice when they step back and step back too, and never touch anyone who has not clearly welcomed it. Creepiness is mostly persistence after a signal to stop.

Flirt like yourself, and say what you mean when the moment comes. If the moment belongs to a later chapter, write it into an IF and save it for that chapter.