To flirt on a walk, choose a comfortable public route, keep pace with the woman beside you and use things you notice together to start playful conversation. You can make a warm remark about something she says, share a little personal interest and occasionally meet her eyes when you stop or turn towards each other. Don't force eye contact, touching or an elaborate romantic speech while you're both watching where you're going. Let the walk be a pleasant shared experience, with the possibility of a second date if you both want one.
Some gentlemen feel completely at ease talking as they walk, yet become strangely formal the moment they're seated opposite an attractive woman at a table.
A restaurant can feel like a small stage. There she is, looking directly at you. Here you are, searching desperately for something fascinating to say about the water glasses.
A walk changes the arrangement. You're side by side, there's always something around you, and a comfortable silence needn't look like a failed interview.
I discovered this advantage by accident while accompanying my friend Hugo on what was supposed to be a sedate afternoon date along the seafront.
He'd planned a graceful stroll beside a woman called Frances. Unfortunately, he'd chosen new shoes, a route with an unexpectedly aggressive hill and an afternoon when the wind was making serious efforts to remove everybody's hats.
“Hugo,” I warned, “romance ought not to require mountaineering equipment.”
He insisted on continuing. Frances laughed and suggested a different path.
That was the first really promising moment of the afternoon: he listened.
Choose the route for conversation, not for photographs
A beautiful view is delightful, but it isn't worth much if the two of you must march single file through mud or shout across a road.
Choose somewhere public, reasonably familiar and easy to leave. A park, promenade, riverside route or town centre with interesting shopfronts can be splendid, depending on the weather and what she enjoys.
Ask whether she'd like a walk rather than declaring it the plan.
“How do you feel about a wander through the gardens and a coffee afterwards?”
If she doesn't fancy walking, suggest something else.
Keep the route manageable. People vary in mobility, footwear, comfort and interest. Do not assume she wants to climb a steep hill in delicate shoes merely because you've imagined the sunset photograph.
A good date plan gives you space for conversation and the freedom to finish or change direction when you both choose.
Romance becomes less charming when one of you is struggling to find a bench.
Walking side by side changes the conversation
You needn't stare directly at each other throughout the date.
That can make it easier for someone who feels self-conscious sitting face to face. You're looking ahead, occasionally turning towards each other and sharing the sights around you.
You might stop beside a particularly extraordinary statue and ask what she thinks the sculptor intended.
If she decides it resembles a confused goose, you may develop a little private joke about the statue's artistic dignity.
But remember that an enjoyable walk is still about the other person, not a running commentary on the architecture.
Listen when she speaks. Offer your own thoughts. Ask about something she's told you, then allow her to ask about you.
A good conversation has direction without needing a destination printed on a map.
If you're walking quietly for a moment and it feels comfortable, you don't have to fill the silence simply because there's no waiter arriving with the next course.
Flirting begins with shared moments
Perhaps she points out a beautiful old house and says she'd love to live there.
You could say, “Excellent choice. I'd better warn you that I'm absolutely hopeless with grand staircases.”
Or perhaps she admits she always gets lost, even in familiar places.
“I can offer navigation, though my last expedition ended in a car park behind a garden centre.”
The purpose isn't to be funny every minute. You're responding to something she actually said and allowing a little warmth between you.
If she laughs and joins in, continue. If she's not playful, you can talk normally without treating the silence as a disaster.
Some of the finest flirtation is a small shared joke that appears naturally and returns later.
The goose statue may become “your new country estate”. An unexpected downpour may become your joint misadventure.
You cannot manufacture these details in advance. That's part of their charm.
Walk at her pace, not the pace of your ambitions
Hugo's unfortunate habit was charging ahead whenever he became nervous.
Frances would begin describing a family trip, and Hugo would accelerate as though delivering the story in person to the next town.
Don't do that.
Match a pace that lets both of you talk and enjoy the surroundings. Check whether she's comfortable without repeatedly interrogating her about the condition of her footwear.
If the path narrows, you can step aside. If the route becomes unpleasant, suggest an alternative.
You can be considerate without assuming she needs escorting like visiting royalty.
And if you'd like to look at her while she makes a point, turn your head briefly when it's safe. You don't need to walk backwards so that the conversation can be conducted face to face.
A gentleman can be attentive and still avoid walking into a bollard.
Don't turn a walk into an unwanted touching exercise
There's some peculiar advice suggesting that the purpose of walking dates is to develop physical contact through a series of staged manoeuvres.
It makes the whole business sound like training for a pickpocket.
You don't need to engineer accidental bumps, grab her elbow or insist on taking her hand.
If there seems to be mutual romantic warmth, allow affection to develop naturally and be sure it's welcome. A straightforward question about holding hands is better than simply assuming.
If she's walking with space between you, don't keep moving closer to close the gap. If she moves away from a touch, respect it immediately.
The purpose of the walk is to get to know her and enjoy being together. Physical closeness may happen if both people want it. It isn't a target to achieve before you reach the next bench.
Some attractive moments consist entirely of talking and laughing while the wind ruins both your hairstyles.
How to give a compliment while walking
A walking date often provides opportunities for compliments that feel personal.
Perhaps she tells you a wonderful story about a trip abroad.
“I like the way you tell things. You make even a missed train sound like an adventure.”
Or she spots a tiny detail in a building that you've walked past without noticing.
“You've got a brilliant eye for things. I'd never have seen that.”
These remarks can be warmly flirtatious when they arise from the interaction.
You could also simply say, “I'm having a lovely time with you.”
There's no need to stop suddenly, turn her to face you and deliver a speech. A compliment can arrive while you're walking together, followed by a smile.
If she seems delighted, excellent. If she's uncomfortable, don't repeat the compliment or demand to know why.
You can admire a woman without expecting her to respond according to a script.
When to stop walking and let a moment happen
A side-by-side conversation sometimes creates a natural reason to pause.
You've reached a lookout, found an interesting market stall or discovered that the sea appears to be staging a particularly dramatic performance.
Stop and enjoy it.
The change of pace can allow a little face-to-face conversation without making it forced. Perhaps you share a joke about the view or discuss where you'd like to visit next.
A pleasant quiet moment is fine. So is an honest expression of enjoying each other's company.
Don't assume a picturesque sunset automatically creates permission for a kiss. If affection feels possible, be considerate and make sure she wants it too.
You might also discover that she isn't romantically interested. The view remains perfectly respectable despite this disappointment.
No amount of magnificent scenery can guarantee chemistry.
Hugo, Frances and the war with the wind
Halfway along the promenade, Hugo's hat was seized by a sudden gust and carried towards a row of beach huts.
Frances laughed and ran a few steps after it. Hugo followed, narrowly avoiding a sandwich board advertising afternoon tea.
They eventually recovered the hat beneath a rather offended-looking seagull.
Hugo was mortified.
Frances, however, had been enjoying herself.
“That's the most excitement I've had all week,” she said.
“Then I must warn you,” he replied, “my trousers are equally vulnerable to meteorological attack.”
They laughed and settled on a bench overlooking the water.
For a few minutes they weren't concerned about whether their conversation was clever or romantic enough. They had a ridiculous little experience that belonged to the two of them.
The shared adventure didn't guarantee attraction. But it gave them something to talk about and allowed both people to be themselves.
Hugo's new shoes, sadly, were beyond redemption.
What to do if the weather turns dreadful
The English climate has never displayed much respect for a gentleman's romantic intentions.
Have a simple alternative in mind: a café, a public gallery or somewhere comfortable where the date can continue if both of you wish.
Ask what she'd prefer.
“Shall we duck into the café, or would you rather call it a day?”
It's better to be practical than to insist your original plan is romantic when both of you are damp and miserable.
If the weather improves, you might continue outside. If not, there's nothing wrong with a warm drink.
Do not assume your date wants to return to your home merely because it rains. A public alternative keeps the decision comfortable and unpressured.
Romance is often improved by a little flexibility and a reliable coat.
Should you take a walk on the first date?
A short public walk can be a lovely first meeting if you both like the idea.
It may suit people who enjoy moving rather than sitting across a table, but it's not universally preferable. Some women want a café, a gallery, a restaurant or an activity that doesn't involve much walking.
Offer the option and accept her preference.
If you've met online and don't know each other, agree on a public place, a manageable route and a straightforward way to finish the meeting. Let someone you trust know your plans if that helps you feel comfortable.
Avoid isolated paths or remote locations for a first encounter. Deserted woodland isn't always a comfortable place to meet a stranger.
Thoughtful planning gives the actual connection a chance to develop.
Turn a successful walk into another date
As you return to the starting point, you can be clear if you've enjoyed the afternoon.
“I've had such a good time. Would you fancy dinner together next Friday?”
Perhaps your shared interests suggest something better: an exhibition, the bookshop you passed or a concert she's mentioned.
Make the invitation easy to answer. If she accepts, lovely. If she declines, thank her for the company and don't try to change her mind while you're still walking.
No special farewell choreography is required. If physical affection isn't obviously mutual, a warm goodbye is perfectly fine.
You can also decide that, pleasant as the stroll was, the attraction isn't there for you.
A walk is a chance to discover whether you want to see someone again, not a commitment to produce a romance by the end of the route.
Monty's final observation from the promenade
Hugo and Frances eventually reached the café we'd intended to visit in the first place.
They were windswept, cheerful and carrying one rescued hat that looked rather worse for its adventure.
Hugo asked whether she'd like to meet again. She suggested visiting the small maritime museum the following week.
He'd rarely enjoyed a date as much.
It wasn't just the scenery. He'd allowed the afternoon to become a shared experience rather than a performance at which he needed to say exactly the right thing.
That is the joy of flirting during a walk. You can look outward together, find reasons to laugh, share opinions and let interest show through ordinary kindness and attention.
If you want more help with those first conversations, I've written a free little introduction titled 7 Secrets to Becoming a Babe Magnet. You'll find its invitation elsewhere on this page.
And do take a decent hat, old boy. The seagulls have developed quite expensive tastes.