You can flirt without saying a word about a woman's looks. Show interest in what she says, share a little playful humour, notice her choices, and suggest spending time together when the conversation feels mutual. A smile, a shared joke and a clear invitation can carry romantic interest perfectly well. You don't need to inspect her dress, hair or figure as though you're judging a county show.
In fact, there are evenings when the most interesting thing about a woman has absolutely nothing to do with what she's wearing.
Some men believe that the first thing they must do is tell a woman how lovely she looks. You can spend an entire evening doing that and never learn what she enjoys, what makes her laugh or whether the two of you have anything in common.
There's a better opening available: listen to what she's saying and contribute something worth responding to. The conversation is not a beauty contest, old boy.
Start with curiosity, not a verdict
An appearance compliment delivers a judgment. A good opening conversation offers something to explore together.
Suppose you're waiting for the beginning of an outdoor concert. The woman beside you is holding a programme and shaking her head at the running order.
Rather than opening with "You have beautiful eyes", you might say, "Are you judging the set list or deciding whether we should make a run for it?"
She says she's delighted about the opening act but distrusts the headliner.
"Excellent. Then I shall pretend to know far more about the opening act than I do. Who should I listen out for?"
Now you're talking about something she has an opinion on. If she answers enthusiastically, follow her point. If she offers a short answer and turns away, leave it there. Being in the same queue is not consent to a prolonged conversation.
The important difference isn't that your opener is cunning. It's that it gives her a comfortable choice about whether to continue.
Make a small shared observation
Flirting often begins with two people noticing the same ridiculous thing.
At a food market, a stall advertises a cheese as "aggressively mature". You glance at it and say, "Rather a harsh way to describe a gentleman of my age."
If she laughs, there may be room for a conversation about favourite foods. If she says the cheese is marvellous, you can disagree with suitable theatrical concern. If she doesn't respond, don't repeat the line louder.
This works because the humour belongs to the moment. You're not making her appearance or personality the target.
Other situations offer perfectly ordinary material. A museum guide who speaks about a teapot as if it won a naval battle. A café menu with eleven kinds of water. A dog that refuses to walk past a particular lamppost.
One gentle remark is plenty. If you're manufacturing observations every twenty seconds, you aren't flirting; you're providing unwanted running commentary.
For more examples of light conversational play, see how to flirt without being naturally funny.
Show that you've remembered something
A woman tells you she has just started learning Italian. Later, you pass a sign with a dramatic Italian name and ask whether she can rescue you from your dreadful pronunciation.
Or she says she hates crowded venues. When the bar becomes noisy, you suggest moving somewhere quieter instead of forcing her to shout.
Neither moment requires a compliment. Both show you heard her.
Paying attention is more than memorising a fact to use later. It means allowing what she's told you to change the conversation.
If she mentions an upcoming presentation and then you see her another time, asking "How did it go?" is warm without being showy. Be interested in the answer, even if the answer isn't entertaining.
Don't turn remembered details into a dossier. Recalling a story she chose to share is thoughtful; listing things you've discovered from her old social posts can feel unsettling.
Let your own personality appear
Some men remove appearance compliments from their flirting and accidentally remove themselves too. They ask questions, nod politely, then wonder why the exchange feels like a customer satisfaction survey.
You need to contribute.
She says she loves early morning walks. You tell her you'd be willing to appreciate the sunrise if someone invented a more civilised hour for it.
She says she restores furniture. You confess your own attempt at repairing a chair ended with a perfectly good chair and an entirely unnecessary screw left over.
Share something genuine. A difference of opinion is fine. You don't have to agree that her favourite film is a masterpiece to enjoy discussing it.
And don't pretend to have hobbies, opinions or travel experiences you don't. If she loves sailing and your only nautical expertise comes from watching a television documentary, ask about it. A fabricated yacht story is particularly difficult to maintain when somebody asks where you keep the boat.
Flirt with a playful challenge, not a personal criticism
You can create a little romantic energy by making a harmless difference of opinion into a game.
She claims the lemon dessert is the best thing on the menu. You say, "An outrageous claim. I fear we're going to need a proper tasting panel."
If she plays along, you might agree to share two desserts. If she doesn't, order the pudding you fancy and get on with the evening.
The challenge should be about something low-stakes and freely chosen: a film, a board game, a restaurant recommendation, an outrageous prediction about which dog will win the local charity race.
Avoid using her body, age, job performance, education or personal insecurity as the battleground. That's not cheeky charm. That's a man looking for an argument and calling it romance.
If you're naturally a bit provocative, my guide to flirting without making a woman uncomfortable looks more broadly at how to spot when playfulness isn't welcome.
Ask a question with somewhere interesting to go
"How was your week?" can be perfectly fine. So can "What do you do?" The trouble comes when you fire them off without listening.
Try a follow-up that belongs to her answer.
She says she has started taking photographs of birds. Rather than asking her to list every bird she's photographed, you might say, "What was the one you were most delighted to catch?"
Perhaps it was a kingfisher that appeared for half a second after three hours of waiting.
"Three hours? That's dedication. I struggle to queue for a sandwich without losing faith in humanity."
You have learned something about her patience, and she has learned something about your comic inability to wait. You can let the conversation wander from there.
A question can also be as simple as "What happened next?" when she's telling a good story. Resist the urge to make every reply clever.
Don't turn listening into a technique
There's a peculiar breed of dating advice that tells you to repeat a woman's last three words, copy her gestures and count the seconds before smiling.
Good heavens. You're meeting someone, not trying to operate a burglar alarm.
Listen because you're interested. If you aren't interested in anything she's saying, investigate that possibility rather than performing the appearance of fascination.
There may be common ground, and there may not. Both outcomes are useful. A polite conversation that doesn't become a romance is not a failed mission.
If she mentions something serious, such as caring for a parent or losing a job, stop fishing for a joke. Respond with care and let her decide how much to share.
If she wants to return to lighter subjects, follow her lead. A woman shouldn't have to keep the evening entertaining for you.
Make it clear this is flirting, not merely friendliness
Here's the sensible objection. If you're avoiding comments about her appearance, how does she know you're interested romantically?
You tell her, through your attention and eventually through an invitation.
"I've really enjoyed talking with you."
"I'd like to see you again, just the two of us."
"Would you fancy coffee this weekend?"
Those are ordinary sentences, yet they're clearer than fifteen vague compliments.
You can be gently playful about the invitation when you already share a joke. If the two of you have been discussing disastrous cooking experiments: "I know a café where neither of us is allowed near the stove. Fancy trying it on Saturday?"
Make the invitation easy to decline. If she says no, says she is seeing someone, or looks uncomfortable, accept the answer without trying to negotiate.
Your ability to hear a no matters more than the elegance of the line.
What if she compliments your looks first?
Wonderful. Say thank you. You aren't required to retaliate with a matching compliment about her appearance.
Suppose she admires your outrageous jacket. "Thank you," you might say, "It's very brave. I'm still deciding whether I am."
If she asks where you found it, answer. Perhaps there's a story. Perhaps the moment passes.
Or you can simply say, "That's kind of you." Then carry on with the conversation.
Avoid announcing, "I never compliment women's looks." It sounds like a principle you're trying to earn a certificate for. She asked about the jacket, old boy, not for your personal manifesto.
If a relationship develops and both of you enjoy affectionate appearance compliments, there's no ban on them. The point is that you needn't rely on them to begin.
Flirting at a party, on a date and by message
At a party, share the situation. Ask how she knows the host. Build from the answer rather than immediately judging her outfit. Don't follow her from group to group to keep the conversation alive.
On a first date, the conversation has already been framed romantically. You can be warmer and more direct: "I've been looking forward to hearing the rest of that story." That doesn't make any assumptions about physical closeness.
By message, return to a topic she enjoyed. "You were right about that book. I've just reached the chapter with the missing painting and am now suspicious of everybody." It's personal and gives her something to answer.
With someone you've known a while, mention a shared experience and ask if she'd like to do something together. Keep the invitation clear enough that she knows it is a date, rather than a mysterious meeting about coffee.
Across all these settings, notice whether the effort runs both ways. A woman who replies politely but never takes up an opening might simply not want to flirt.
The mistakes that make non-appearance flirting feel odd
One mistake is replacing "You're beautiful" with extravagant praise of a woman's courage, intelligence or supposed extraordinary spirit. If you barely know her, how could you honestly judge her entire character?
Another is being so careful not to comment on appearance that you never indicate romantic interest at all. You can be respectful and still say, "I'd like to take you out."
A third is treating every shared laugh as a hidden sign that she fancies you. A laugh tells you she found something funny. The clearest way to find out whether she'd like a date is to ask and listen to her answer.
Think back to that conversation at the concert. If you both enjoyed talking about music, you could finish by saying, "I'd like to hear more of your recommendations. Fancy coffee next week?" That's all that's needed.
Don't memorise a list of 'successful' non-appearance lines. Look for an actual connection and speak naturally about it. The aim isn't to win points for what you didn't say; it's to give two people a chance to enjoy meeting.
If you'd like more of Monty's advice on meeting women without becoming a walking collection of rehearsed lines, the free 7 Secrets to Becoming a Babe Magnet is waiting for you.