To flirt on a first date, start by getting to know the woman, then show that your interest is personal rather than merely polite. Make an observation you can both enjoy, give an occasional genuine compliment, share a little playful disagreement if she likes that sort of thing, and tell her when you're enjoying her company. Watch whether she willingly joins in. If the warmth is mutual, suggest another date. You don't need rehearsed chat-up lines, constant teasing or an obligatory kiss at the end.
I met a gentleman called Julian outside a rather smart little restaurant in Bath. He'd arrived twenty minutes early with a new jacket, beautifully polished shoes and a peculiar expression of terror.
Inside was a woman named Eleanor whom he'd met through a dating app. They had enjoyed a week of lively messages. Tonight would be their first proper meeting.
“I've memorised six flirting techniques,” Julian told me.
“Splendid. Can you remember her name?”
“Eleanor.”
“Then you're already ahead of several chaps I know. Forget the other six.”
He looked appalled.
Julian was a decent man. His only problem was believing that a first date needed to turn romantic according to a timetable: compliment at seven-fifteen, cheeky observation at seven-thirty, meaningful eye contact before the main course, romantic culmination beside the taxi rank.
My dear fellow, a woman is not a theatrical performance with a running order.
A first date offers something much more interesting. Two people who have found each other intriguing get to discover whether the interest survives the arrival of actual personalities.
Let the first ten minutes feel like meeting someone
Greet her warmly. If you're unsure whether she'd welcome a hug, follow her lead or ask. Tell her it's lovely to meet in person.
Then deal with the ordinary business of arriving. Find the table. Look at the menu. Let her get comfortable.
There's no need to open with “You have the most extraordinary eyes I've ever seen” while she's trying to untangle her scarf.
You might refer to something from your messages: “You said the journey here could be an adventure. Did the trains behave themselves?”
Or you can ask how her day has been. Not every sentence needs to sound original.
The first few minutes are useful because they establish whether the conversation feels easy. You're both adjusting to meeting outside a screen or introduction.
Once you've had a little genuine exchange, flirtation has something real to build upon. Before that, a carefully prepared line is often just a stranger announcing his intentions at an inconvenient volume.
Make the compliment specific to her
A first-date compliment can be simple: “You look lovely tonight.” If she's pleased, excellent. Don't immediately deliver three more.
But some of the sweetest compliments emerge from the conversation rather than from her appearance.
Perhaps she explains how she accidentally became the organiser of her entire family's holidays.
“You make all that sound like a grand adventure. I love how enthusiastic you are.”
Or she tells a story that has you laughing.
“I had a feeling you'd be good company, but I wasn't expecting to laugh quite this much.”
Those observations show that you're paying attention to her.
Avoid describing her body in intimate detail or placing her on a pedestal. A first date is not permission to give a full appraisal of a woman you barely know.
Say something you mean and let it stand. Compliments aren't tickets that must be exchanged for affection.
The dinner menu provides a magnificent opportunity
Julian and Eleanor sat down. The menu contained a dish described as “deconstructed garden vegetables on a landscape of fermented heritage”.
Eleanor raised an eyebrow.
“Is that a salad?” she asked.
Julian glanced at me across the room. I made a discreet gesture suggesting that he might respond as a human.
“I think,” he said, “that the vegetables have been through a difficult divorce.”
Eleanor laughed.
A tiny joke, shared at the right moment, was worth far more than his six techniques.
He hadn't insulted the waitress, rehearsed a line or tried to create artificial intimacy. He'd simply noticed something funny and allowed Eleanor to play.
When she wondered what a “heritage landscape” tasted like, he suggested they order it and investigate.
That's often how first-date flirting begins. You're no longer merely exchanging biographies. You're enjoying the same small experience.
Banter is an invitation, not a contest
If she has a playful sense of humour, you may enjoy a little teasing about harmless subjects.
She says her favourite film is one you consider a complete disaster. You can grin: “That's a serious disagreement for this early in our acquaintance.”
If she laughs and defends her choice, carry on. If she looks puzzled, let the joke go.
Don't mock her intelligence, background, accent or appearance. And don't spend the evening trying to win every exchange.
Banter works when she gets to contribute something clever or ridiculous herself. It's a little game you both choose to play.
Julian and Eleanor ended up debating whether their strange restaurant could serve chips without describing them as a “rustic potato experience”.
Neither won. Both laughed.
That shared amusement was the flirtation, not the fact that Julian had succeeded in delivering a perfectly timed quip.
Find out whether the interest is mutual
A woman might be friendly, courteous and thoroughly enjoyable company without feeling any romantic attraction. You might feel the same about her.
So consider the whole date rather than any one signal.
Does she ask about you as well as answering your questions? Does she contribute her own stories? Does she seem happy to stay in the conversation? Do you both find moments to smile and laugh?
These may suggest that the evening is going well. They don't prove she wants to kiss you or see you again.
The clearest sign often arrives when you make an appropriate invitation and she chooses whether to accept.
Don't spend the evening counting how many times she touched her hair or looked at your mouth. That's an appalling way to enjoy a decent dinner.
Pay attention to her words and comfort, and keep your own interest honest.
Let a quiet moment stay quiet
There will probably be a pause. A waiter takes the plates away. Somebody orders another drink. Perhaps you've finished a topic.
Don't panic and produce a joke about marriage.
You can smile, look at the room or take a sip. Sometimes a pleasant silence feels like part of the evening.
If you want to restart, return to something she said earlier.
“You mentioned you were learning to sail. What made you take that up?”
Then listen.
A man constantly trying to be charming can become surprisingly tiring. A man capable of enjoying an ordinary pause is rather easier to sit beside.
If she's looking at her phone or indicating she's ready to leave, that may be a different sort of quiet. Respect her cues instead of filling the moment with louder flirtation.
Move beyond friendly questions when the time feels right
Some excellent first dates never become romantic because the man stays determinedly neutral.
He asks about her work, her holidays, her hobbies and her favourite pudding. She may reasonably conclude that he's conducting a very pleasant conversation with no particular interest in her.
A little warmth can make the distinction.
“I've really enjoyed getting to know you tonight.”
“You're great fun to talk to.”
Or, with a gentle smile after a shared joke: “I'm beginning to suspect we'd be quite good at getting into harmless trouble together.”
Don't say these things because a script demands it. Say them when they genuinely reflect the way you're feeling.
If she responds warmly, enjoy that. If she doesn't, return to ordinary conversation or finish the date politely.
One good flirtatious moment doesn't create an obligation for another.
Keep physical closeness separate from verbal flirting
Julian had been told that a man needed to touch a woman's arm three times during a date or risk being “friend-zoned”.
I told him to throw away this advice with the rest of the nonsense.
There is no required quota for touching. A laugh, a compliment or mutual enjoyment doesn't automatically authorise physical affection.
If you're thinking of a hug or kiss, notice whether she's actually comfortable and ask where you aren't sure. She's entitled to decline, and you're equally entitled to move at a pace that suits you.
You needn't engineer accidental contact while passing the bread basket. It's possible to be warmly flirtatious without touching at all.
A woman who's interested may welcome affection. A woman who isn't must have room to say so without pressure.
Being considerate is not the enemy of romance. It's part of making the experience enjoyable for two people.
How to finish a first date without becoming mysterious
At the end of an evening, don't pretend to be indifferent just because you read that enthusiasm reduces attraction.
If you like her, tell her.
“Tonight's been lovely. I'd like to see you again. How about that little exhibition you mentioned next weekend?”
It's a proposal, not a command.
If she says yes, you can settle the details. If she isn't sure, leave her space to decide. If she declines, accept it kindly.
You don't need to wait an arbitrary three days before following up. Nor should you send repeated messages demanding a reaction.
What matters is being clear about your intentions and respectful of hers.
That will accomplish more than trying to look irresistibly detached while secretly checking whether she's typing.
What if the date is pleasant but there's no spark?
Then you have learned something useful.
Don't exaggerate romantic interest merely because you want to feel successful. A woman may be charming without being someone you want to date.
You can enjoy the meal, thank her for the evening and decide that you won't pursue another meeting.
If she asks directly, be honest and gentle rather than promising something you don't want.
Similarly, if she doesn't want a second date, her decision isn't evidence that you ruined the evening by failing to tell enough jokes.
First dates involve two people making choices, not one man performing until somebody awards him a second appointment.
Julian finally puts away the instruction manual
The dinner continued. Eleanor told Julian about a disastrous sailing lesson. He admitted that he once tried to impress a woman by cooking a meal and set off the smoke alarm before she'd taken off her coat.
They laughed, traded embarrassing stories and found themselves surprisingly interested in each other.
When the waiter brought the bill, Julian didn't deliver one of his memorised lines.
He smiled at Eleanor.
“I've had a brilliant evening. Would you like to do this again somewhere with a less complicated salad?”
She agreed, on the condition that they avoid anything described as “deconstructed”.
That wasn't a victory for the imaginary timetable. It was a moment that had become possible because Julian stopped performing and started enjoying his date.
Flirt with the woman, not the idea of impressing her. Let the chemistry, if there is any, come from the way you talk, laugh and respond to one another.
My complimentary fourteen-page Babe Magnet introduction is waiting below. Consider it a little assistance before your next charming dinner.
And should the menu offer you a landscape of fermented heritage, old boy, order chips.