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FIRST DATESWHEN TO LEAVE

FIRST DATESTHE ART OF MONTY ✳ EST. 2026
THE GENTLEMAN'S READING ROOMARTICLE FILE 038 / 560ALL THE MONTY FILES ↗

For many people, an hour or two is plenty for a first date, particularly if you're meeting for coffee or a drink. That's a guide, not a deadline. Leave while you're both comfortable, and extend the time only if you're enjoying yourselves; a shorter good date beats a long awkward one.

At one end of the first-date spectrum sits a man who checks his watch after twenty minutes, announces that he has 'learnt everything he needs to know' and leaves before the poor woman has finished her cappuccino. At the other sits the fellow who has somehow turned a pleasant drink into a five-hour expedition involving dinner, an improvised pub crawl and a solemn promise to visit her parents in Devon.

Neither has understood the assignment.

So, how long should a first date last? For a first meeting, arranging roughly an hour to ninety minutes is a sensible starting point. Not a compulsory romantic stopwatch, and certainly not a guarantee of a second date. It's simply enough time for two strangers to settle, enjoy a conversation and decide whether they'd welcome another.

I am an enthusiastic admirer of a lingering dinner. But I prefer to linger because the company is irresistible, not because the man who made the reservation has declared that dessert is legally binding.

01 / FROM THE MONTY FILES

Plan for an hour; leave room for the evening to surprise you

Illustrated scene featuring Monty for the article: How Long Should a First Date Last? Long Enough for a Spark, Not a Hostage Situation
THE ART OF MONTYFILE 038 / AN ILLUSTRATED SCENE

The distinction that solves most of this question is between the planned length and the actual length.

A plan should be manageable. 'Shall we meet at six for a drink?' contains no implication that either of you must remain until the bar staff start stacking chairs. If you enjoy yourselves, you can order another, wander to a nearby café or suggest something else. If the chemistry fails to make an appearance, you can leave with everybody's dignity intact.

The advantage is practical as well as romantic. People have work tomorrow, trains to catch, children to collect, anxious dogs to feed and lives that existed before you announced the availability of your dazzling company.

Don't tell her you're allowing precisely seventy-three minutes. That's the sort of detail one expects from a dentist. Give her the meeting point and a clear idea of the occasion. The clock can remain quietly in your pocket where it belongs.

02 / FROM THE MONTY FILES

Coffee, cocktails, dinner: three very different commitments

A quick coffee can comfortably run forty-five minutes to an hour. That makes it useful when you're meeting through an app for the first time, when either of you has a busy schedule, or when a quiet chat would suit you both better than a grand production.

One drink at a pleasant bar might take an hour or ninety minutes. It has more of an evening-date atmosphere, if that's what you're after, but still allows an easy exit. Choose somewhere you can hear one another. A venue with music loud enough to loosen a tooth is an expensive method of learning absolutely nothing about someone.

Dinner is a bigger undertaking. Ordering, eating and paying can easily turn it into two hours or more. Entirely fine if you both want it, particularly if you already know each other or have been talking for a while. But for a first meeting between near-strangers, a three-course meal can feel like sitting through a play you've discovered you dislike during the first act.

A gallery visit, market wander or short walk introduces another variable: the activity itself. Choose a route or setting with natural pauses and a convenient place to finish. A 'little stroll' that unexpectedly requires mountain boots and an emergency blanket may end the romance before the second stile.

03 / FROM THE MONTY FILES

The first fifteen minutes are not a verdict

People rarely arrive as their full, sparkling selves. There are coats to remove, menus to navigate and that tiny mental jolt of recognising a person previously known only as six photographs and a biography claiming an interest in Italy.

An awkward opening doesn't mean the evening is doomed. Give the conversation a moment to find its shape. Ask something genuine; offer something of yourself. Once you've discussed the obvious question about finding the venue, don't make your entire contribution a fresh series of interrogations.

If she seems nervous, she may become warmer once she settles. Equally, sometimes things simply don't click. You don't owe each other instant fascination, and you shouldn't be judging someone as a permanent romantic failure because their opening story involved a disappointing train journey.

The first quarter-hour should help both people get comfortable. It needn't prove that you're destined to dance barefoot on a Mediterranean terrace together.

04 / FROM THE MONTY FILES

The crucial middle: are you enjoying the person or just the occasion?

Beautiful surroundings can flatter a mediocre date. A candlelit room, generous bartender and a bottle of something splendid may make the evening feel dramatic even when you've struggled to discover a single shared interest.

Ask yourself a less glamorous question: would I enjoy talking to her in a fairly ordinary café? Do I want to hear the rest of her story? Am I curious about what she thinks? Does she appear genuinely interested in my answers rather than simply waiting for her turn?

You should also consider your own experience. Some men become so absorbed in whether she likes them that they forget to decide whether they like her. A date is not an audition at which only one person holds the clipboard.

If the conversation has acquired a lovely rhythm, you're allowed to enjoy it. If you're repeatedly finding yourself looking for a way to finish, you don't have to force another hour in the interests of 'giving it a chance'.

There's a civilised middle ground between leaving because a date isn't fireworks and staying until somebody's coat needs retrieving from the lost-property office.

05 / FROM THE MONTY FILES

How to extend a good date without assuming she's agreed

Suppose you've been talking for an hour, the table's getting cleared and neither of you seems in a hurry. A wonderfully unremarkable question will do: 'I'm having a lovely time. Fancy one more, or do you need to get going?'

That wording matters. You're expressing interest and leaving the other person a straightforward choice. If she says she should leave, don't convert it into a negotiation. Some people have genuine commitments; others simply prefer to stop while the date feels good.

Another possibility: 'There's a little dessert place nearby, but absolutely fine if you'd rather call it an evening.' Say it only if there actually is a place nearby and you're comfortable with another outing. A spontaneous invitation is not permission to drag someone through three postcodes.

If she agrees, wonderful. But don't treat the extension as evidence that kissing or further intimacy is now required. Another drink is consent to another drink. Romance, when it happens, is still a shared decision.

And if you're both utterly engrossed, no law requires you to stop at ninety minutes. The point of a shorter initial plan is flexibility, not rationing pleasure.

06 / FROM THE MONTY FILES

When a first date should end early

Not every first meeting warrants its original allotted time. If somebody is rude, aggressive, sexually pushy, intoxicated to the point of making the encounter uncomfortable or simply makes you feel unsafe, you're entitled to leave. You don't owe an awkward extra hour because you ordered a starter.

A polite exit might be: 'I'm going to head off now. Thanks for meeting me.' You don't need to invent a burning warehouse. If you're concerned about safety, seek help from venue staff or a trusted contact. Choose public places for first meetings and keep a way to get home independently.

More commonly, the issue is merely that the conversation isn't taking off. In that case, finish your drink, thank her and go. You can be gracious without pretending to want a second date.

Do not manufacture a telephone call from a fictitious family emergency. It may feel easier in the moment, but a considerate, unexciting goodbye is perfectly respectable.

And if it's going badly for her, allow her to leave. 'Of course, thanks for coming' takes considerably more charm than trapping somebody in a discussion about whether she'd have liked you if you'd chosen a different shirt.

07 / FROM THE MONTY FILES

The goodbye: don't turn a good finish into an awkward encore

A splendid date can be spoiled by lingering too long after the natural ending. There is a moment when the last laugh fades, coats are collected and continuing to hover begins to resemble a man who has forgotten where he lives.

If you'd like another meeting, say so. 'I've enjoyed this. I'd like to see you again' is excellent English and requires no interpretive dance. You can suggest a plan then, or send a follow-up message when you're home.

If you're not interested, you can still thank her warmly. Don't make promises merely to escape the pavement. 'It's been nice meeting you' is enough. If asked directly about another date, be considerate and honest rather than issuing a fictional appointment.

As for the goodbye kiss, there isn't a clock setting that makes one appropriate. Mutual interest matters, and asking is entirely compatible with being confident. A two-hour date doesn't entitle anyone to anything more than the time already shared.

08 / FROM THE MONTY FILES

A pocket-sized decision guide for the evening

Rather than constantly checking your watch, work through the evening in three parts.

At the start: is this setting comfortable for both of you? Can you hear one another, sit conveniently, and get home easily? If the room is hopeless, suggest a reasonable alternative and let her decide.

After some conversation: do you both seem engaged? Are there real questions, stories and curiosity? It's fine if the chat needs a few minutes to warm up, but you're not obliged to rescue an evening that neither of you enjoys.

At the natural pause: offer a choice. Stay a little longer if you both want to. Leave pleasantly if one of you needs to. Don't interpret polite hesitation as an invitation to push.

The beauty of this approach is its lack of manipulation. You're responding to the actual human being sitting opposite, rather than trying to hit an invented target designed by a stranger on the internet.

09 / FROM THE MONTY FILES

Four plans, four perfectly good lengths

Two people meeting for coffee after work might spend fifty minutes together and leave smiling, already discussing a second meeting. Excellent date.

Another couple might enjoy a ninety-minute drink, discover they disagree about nearly everything except films and decide they're not quite suited. Also a worthwhile date: nobody wasted the night pretending.

Two people who've known each other socially for months might arrange dinner and stay until the staff begin their tactful closing rituals. Lovely, because both wanted that time.

And a man who books a museum trip only to discover she's exhausted may suggest sitting for half an hour instead. Consideration can be far more appealing than ploughing through the entire exhibition just because he's bought tickets.

Notice what's absent from these examples: a magical duration that determines success. The length is a result of circumstances and mutual enjoyment, not a numerical key to attraction.

10 / FROM THE MONTY FILES

The time you spend afterwards matters more than the minutes on the clock

When you get home, don't calculate how many minutes she laughed, what percentage of the conversation belonged to you or whether the goodbye lasted long enough to satisfy some self-appointed romance statistician.

Ask whether you were comfortable, whether you enjoyed her company and whether you actually want to see her again. If you do, express it. If not, be kind and clear.

My preference? Begin with a delightful, manageable invitation. Dress as though you made an effort. Arrive on time. Let the woman surprise you. If an hour passes beautifully, that's a success. If two hours disappear because neither of you wants to stop talking, you've got a marvellous problem.

Just don't make the length of the date the main event. A wristwatch has never fallen in love with anybody, even one wearing a very expensive strap.

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