To feel comfortable going on a date alone to a new venue, check the exact address and entrance, arrange your own journey, and agree on a simple place to meet before you set off. Arrive with a few minutes to spare, choose a public setting where you can wait comfortably, and send a brief message if plans change. You don't need a companion to escort you in, a grand entrance or a perfect knowledge of the building. Your job is to find the place, meet your date and enjoy getting to know her.
My friend, there are restaurants with front doors so discreet that a man can pass them three times and begin to wonder whether the whole establishment exists only for people who know the password.
One such place, a fictional little wine bar called The Green Lantern, occupies the courtyard of a converted old mill. An aspiring suitor named Benedict has agreed to meet a delightful woman there at seven thirty.
Benedict has never visited. He's imagined a glamorous entrance beneath a glowing sign. What he discovers instead is an archway, a furniture shop and a small brass plaque that could belong to a solicitor.
He starts pacing past the shop window, increasingly convinced that he's about to become the only man in Lancashire to miss a date while standing three metres from the restaurant.
An excellent opportunity to discuss the practical side of arriving at an unfamiliar venue, because the actual romance ought to begin after you have found the door.
Establish precisely where you're going
A venue's name is not always enough. Some pubs, hotels and restaurants have similar names, several branches or entrances on different streets.
Before the date, check the full address, postcode and map location. Look at the venue's own website for access notes or photographs of the entrance if it has them.
“Looking forward to Thursday. Shall we meet just inside the main entrance at 7.30?”
You've settled two pieces of information that can otherwise create ten unnecessary messages while one of you stands by the wrong door.
No need to spend half your life studying a satellite image. The object is to remove practical confusion, not acquire a qualification in urban planning.
Give yourself enough time to arrive like a human being
An unfamiliar venue may take slightly longer to find than the café you know. Allow for transport, walking from the station and locating the entrance.
Arrive with enough time to find the entrance, rather than waiting for ages beside a flowerpot.
A few minutes of comfortable margin is useful. If you've arrived much earlier, you might look in a nearby shop or sit somewhere pleasant before going to the meeting spot at the agreed time.
If the bus or train runs late, tell her simply. “I'm running around ten minutes behind because of the train. I'll message when I'm at the entrance.”
Don't manufacture an outrageous story about a mechanical breakdown when you merely left later than intended.
Reliability is attractive. It shows you understand that her time matters as well as yours.
And if you discover that you're genuinely lost, ask staff or someone at the venue for directions rather than wandering ever more heroically in the wrong direction.
Arrange your own journey home
Especially on an early date or when meeting someone from an app, it's sensible to have your own way there and back.
That could be public transport, a booked cab or your own car. Know roughly when the last convenient train leaves and whether the route to the station is straightforward.
If the person is new to you, choose a public venue and let a trusted friend know where you'll be. You needn't share an address or rely on the woman to collect you from home.
The same courtesy applies to her. Don't insist on picking her up or making the arrangements more intimate than she wishes.
A date should give both people the freedom to enjoy the evening or end it when appropriate.
Good preparation isn't a declaration that you expect something dreadful to happen. It's the reason practical concerns can remain in the background while you both have fun.
Monty is fond of a spontaneous late-night escapade, but he's also rather fond of knowing which station the train departs from.
What to do once you've arrived
You've found the entrance. You're a few minutes early. There is no sign of your date yet.
Rather than circling the building as if auditioning for an undercover role, choose the agreed meeting point.
If it's a restaurant, you can tell the host you're meeting someone. Ask whether it's better to wait by the bar or at the table. If it's an exhibition, wait near the stated entrance without blocking the doorway.
When she arrives, smile and say hello. If you haven't met before, check you're greeting the right person.
“Hi, Rebecca? I'm Ben. Lovely to meet you.”
That's the entrance. Nobody need produce a trumpet.
You may discover she's also never been to the place. You can both laugh about the confusing courtyard. The small absurdities of arriving somewhere new can make a perfectly good first conversation.
The goal is not to appear as though you own the building. It's to be pleasant to spend time with inside it.
When there's a reception desk, dress code or booking
Some venues have arrangements unfamiliar to newcomers. A small members' bar may require a booking name. An exhibition might have tickets collected from a desk. A restaurant may take coats as you arrive.
None of this is an examination of your social standing.
Read the confirmation. Keep booking details where you can find them. If there's a dress code, dress appropriately. If you're unsure where to wait, ask somebody who works there.
“Excuse me, I've booked a table for two under Bennett. Where would you like me to wait?”
That's all.
If you feel embarrassed not knowing the procedure, remember that the staff handle first-time visitors routinely. Their job is to help the evening run smoothly, not laugh at a man who doesn't know which door leads to the cloakroom.
And if you've chosen a place far grander than your ordinary haunts, don't begin apologising for being unfamiliar with it. Enjoy learning somewhere new.
A magnificent restaurant is a room in which people eat dinner. The chandeliers do not issue social certificates.
If she arrives first
Perhaps you thought you were early, but she's already at a table, sipping something and reading the menu.
There's no need for a theatrical apology unless you've actually kept her waiting.
“Lovely to see you. Have you been here long?”
If she says she's just arrived, splendid. If she's been waiting because you were late, apologise briefly and settle in.
Don't spend the first course explaining traffic conditions in painstaking detail. She came for your company rather than a documentary about roadworks.
Take a look around, order something you'd genuinely enjoy and join the conversation.
If the table location is uncomfortable for either of you, ask politely whether another is available. A quieter seat can be useful, particularly when the aim is to talk.
The venue is there to serve the date, not the other way round.
If you go to the wrong entrance
Return to Benedict and The Green Lantern. He has reached the courtyard but is now standing beside a locked gate intended for deliveries.
A small sign points to an entrance around the other side.
He could announce a catastrophe and compose a paragraph about his incompetence. Or he could walk to the correct door.
If he's genuinely delayed, he can message Rebecca: “I found the delivery entrance instead of the wine bar. I'm round the corner—see you in a moment.”
She may laugh. She may have made precisely the same mistake.
The practical solution is not to hide, abandon the date or invent a dramatic explanation. It's to find the right place and communicate if necessary.
You can even allow the mishap to become part of the evening's gentle humour, provided it doesn't require her to spend twenty minutes locating you.
One wrong turn should not be allowed to steal the whole date.
When the venue isn't what you expected
Perhaps the place is much louder than the photographs suggested. Perhaps there's a private function, the bar has closed early or the table is beside a very enthusiastic birthday party.
A gentleman can solve practical problems without treating them as personal romantic failure.
If you can't hear one another, ask whether there's a quieter seat. If the venue is unexpectedly closed, suggest an alternative nearby and let her decide whether that suits her.
“The little café around the corner is open and looks much quieter. Shall we try there?”
That's teamwork, not an admission that you've ruined everything.
If the alternative doesn't appeal, you can agree to rearrange for another evening. Two people may have completely different ideas of a pleasant place to meet; that's useful information.
And if you feel genuinely uncomfortable or unsafe, you're entitled to leave. Nobody's agreement to a date overrides their ability to change their mind.
The finest hosts adapt to circumstances, even when they aren't technically hosting.
Don't perform expertise you don't possess
Benedict finally enters the wine bar. There is a list containing seventeen wines whose names he would struggle to pronounce even after four lessons.
He is tempted to pretend he knows precisely what every vineyard produces.
What a tiresome evening that would become.
If you don't know something, ask. “I usually drink red. What would you suggest that's not too heavy?”
If you don't drink, say so and choose something you enjoy. If the menu is unfamiliar, take your time.
There's a peculiar charm in two people discovering a new place together. You can compare the menu, admire the room or laugh about the interesting artwork.
You aren't required to become an expert in architecture, wine or the local history of a converted mill simply because you're spending an evening there.
The woman across the table is hopefully more interested in your company than your ability to pronounce the name of a grape.
The date itself deserves your attention
Once you've found the venue and greeted her, try not to keep revisiting how well you handled the arrival.
It doesn't matter whether you found the entrance on the first attempt or asked a porter which way to go. What matters now is whether you enjoy talking.
Ask about something she's mentioned. Share a funny story. Offer an observation that actually interests you. Notice whether you're both contributing and whether the conversation has warmth.
Perhaps you'll find that you're not particularly compatible. Perhaps the evening will fly by and you'll agree to meet again.
The unfamiliar surroundings may even become a shared pleasure. You could discover a wonderful little bar you'd never have found on your own.
If you fancy her and have enjoyed the evening, say so clearly. “This has been lovely. Would you fancy meeting again next week?”
You don't need to score points for discovering the secret entrance. Though I admit it may deserve a small celebratory flourish.
The lantern finally appears
Benedict discovers that The Green Lantern is named after a tiny lamp above its actual doorway. Rebecca is waiting inside, laughing because she also struggled to find the place.
They spend the first few minutes comparing their adventures through the courtyard. He admits that he nearly asked the furniture shop whether it served wine. She tells him she tried the locked delivery gate.
Before long they're talking about travel, old buildings and a ridiculous holiday in which a hired car took them to the wrong village.
Perhaps they'll like one another enough for another meeting. The point is that the awkward arrival didn't decide the outcome.
If you're going on a date alone to somewhere new, establish where you're going, arrive sensibly, keep your travel arrangements simple and allow the venue to become part of an enjoyable evening rather than a test of courage.
And if you ever find a bar concealed behind a furniture shop, do let Monty know. I have an exceptional weakness for places with secrets and decent olives.