On a first date, talk about things that invite stories: places you've enjoyed, funny mishaps, passions, family traditions or what you both want to try next. Ask questions you genuinely care about and offer something of yourself in return. You're looking for a flowing conversation, not conducting an interview.
A first date is a peculiar arrangement. Two people who barely know each other agree to spend an evening discovering whether they'd like to spend another evening doing exactly the same thing. One of them is nervous about the conversation. The other is nervous about the conversation. Both pretend to be absolutely fascinated by the menu.
Then comes the dreadful question: “So, where do you see yourself in five years?”
Good heavens. She's ordered a glass of wine, not applied to be regional sales director.
A gentleman asked me once what he should talk about on a first date, and I told him the question was perfectly sensible but slightly upside down. The aim isn't to cover a predetermined list of topics. It's to leave the table having discovered what this particular woman is like, and having given her a proper chance to discover the same about you.
The conversation should feel like an enjoyable evening, not an assessment centre with better lighting.
That doesn't mean you walk in without a thought in your head. Having a few good starting points is tremendously useful, especially if nerves tend to turn your imagination into cold porridge. Here's how I'd approach it.
Begin with the evening you're actually having
You sit down. The waiter brings menus. There's music, people arriving, an interesting painting above the bar, perhaps a remarkable amount of velvet in a room that doesn't seem quite prepared for it.
Start there.
“Have you been here before?” is fine, but rather forgettable on its own. “I'm trusting you to stop me ordering the most disastrous thing on this menu,” gives her something playful to work with. If she knows the restaurant, ask what she likes about it. If it's new to you both, you've got a tiny adventure to share.
A first date doesn't need an explosive opening. A relaxed minute discussing the place can settle both of you. From there, let a detail lead somewhere personal.
She says she loves little restaurants because her family used to go exploring on Sundays. Suddenly you're talking about childhood outings, family traditions or the worst meal either of you has ever been served.
The shared setting was only the doorway. The interesting bit is the person on the other side.
Ask about experiences, not just personal statistics
“Where do you work?” “How many brothers and sisters have you got?” “What part of town do you live in?”
None is forbidden. But after ten minutes the conversation starts to resemble an insurance application.
What makes someone's life interesting isn't simply the headline. It's how they feel about it.
If she works in a hospital, you needn't ask her salary, shift pattern and promotion prospects. You might ask what surprised her about the job, or what a genuinely good day there looks like. If she has just returned from holiday, ask which moment she'll remember longest rather than requiring a full itinerary.
A particularly good question invites a story: “What's the most spontaneous thing you've done recently?” Or: “Was there a place you expected to hate and ended up loving?”
These questions have room for personality. One woman might describe climbing a mountain; another might recount buying a sofa so enormous that it had to be delivered through a neighbour's garden. Both tell you more than “I enjoy travel and home improvement.”
And don't fire them out like a quizmaster. One good question, followed properly, can carry a conversation for twenty minutes.
Find out what lights her up
Everybody has something that brings a different expression to their face. Perhaps it's an obsession with old cinemas, restoring motorbikes, competitive baking, the local football club or rescuing ancient furniture from skips.
When you find it, stay a while.
Ask how she got into it. Ask what people misunderstand about it. Ask what she'd do with an entire free weekend and no obligations. The most rewarding answers are rarely the ones you predicted.
Now, an important warning to my fellow gentlemen: curiosity is not pretending to agree with absolutely everything.
If she loves cold-water swimming and you consider a chilly bathroom floor a personal attack, you don't need to announce that you're thinking of taking the plunge. You can say, “I admire the courage. Personally, I believe water should be warm enough to host a respectable cup of tea.”
There you are. You've revealed something about yourself, made room for a laugh, and avoided signing up for a hobby that would have you shivering beside a lake at six in the morning.
Tell stories of your own or you'll become the interviewer
One of the easiest first-date mistakes is asking excellent questions and contributing almost nothing yourself.
She tells you about her disastrous attempt at pottery. You laugh, ask another question, then another. Before long she has revealed her dreams, hobbies and entire biscuit preferences, while she still doesn't know whether you possess a personality or merely a notebook.
Offer a related piece of yourself.
Perhaps she describes the lopsided vase she brought home. You admit that your last attempt at making something involved assembling a flat-pack wardrobe backwards, then having to pretend the unusual door arrangement was intentional.
Good stories are not necessarily grand stories. They have a beginning, a complication and a detail that makes them yours. A five-minute monologue about your professional achievements is less interesting than a thirty-second account of what happened when you tried to impress your nephew by cooking pancakes.
Choose anecdotes that give her something to respond to. Leave space for her reaction. If she's laughing or asking questions, keep going. If she's looking past your shoulder, bring the plane in for landing.
A date is a duet, not your farewell performance at the London Palladium.
Talk about what you enjoy, what you value and what you hope to do
A good first date should eventually move beyond weather reports and restaurant reviews. You're trying to find out whether you like each other, after all.
That doesn't require an interrogation about marriage by the starters. It might mean talking about what makes a weekend feel worthwhile, why a friendship matters, what you'd love to learn, or which small things make ordinary life better.
Try asking, “What's something you've been looking forward to lately?” That question has a much friendlier sound than “Explain your long-term life objectives.”
Her answer might be a holiday, a qualification, finally sorting out her garden or an evening with old friends. You get a glimpse of how she lives and what matters to her.
You should be equally willing to answer. If you're looking for a relationship, there's no need to disguise that behind a carefully rehearsed performance of indifference. You can be honest without presenting a ten-year plan before the main course.
The best conversations become a little more personal as comfort grows. They don't leap from “How's your pasta?” to an exhaustive analysis of someone's childhood wounds.
What not to talk about on a first date
People love absolute lists on this subject. Never mention politics. Never mention an ex. Never talk about money. Never discuss anything serious until date number four, after a suitable ceremonial announcement.
Life isn't quite that tidy.
You can talk about serious subjects if they arise naturally and both people are comfortable. You can mention a previous relationship when relevant without turning the evening into a prosecution of your former partner. You can be open about major values without demanding instant agreement.
The trouble begins when a topic becomes a test, a rant or a captive audience experience.
Avoid grilling her about sexual history, demanding explanations for being single, complaining at length about women you've dated, or boasting about your income as though you're auctioning yourself beside the pudding trolley.
And if you disagree? Splendid, occasionally. Two adults can disagree about something without summoning a tribunal. Ask why she sees it differently, share your view, and notice whether the exchange is enjoyable or making her uncomfortable.
If a sensitive subject lands badly, you can simply say, “We've managed to make dinner sound like Question Time. Tell me something considerably more fun.” Then change direction.
Handle awkward silences without declaring a national emergency
There will probably be a pause. Perhaps the food arrives. Perhaps you both take a sip of your drinks. Perhaps a waiter asks whether everything is satisfactory while one of you has half a potato in your mouth.
All perfectly survivable.
A moment of quiet isn't proof the date has failed. Don't rush to fill every second with a prepared question, especially when she's still chewing.
If the conversation genuinely stalls, return to something she mentioned earlier. “You said you were planning a trip to Edinburgh—have you decided what you're doing there?” shows you listened and gives the evening a natural thread.
Or share an observation about where you are. Or admit, with a grin, “I've just lost the point of that story completely.” A little self-awareness can be more appealing than desperately pretending every sentence has been flawless.
The greater danger isn't a pause. It's becoming so frightened of silence that you stop paying attention to the person in front of you.
How to know the conversation is going well
Don't judge the date by whether she laughed at every joke or by how many minutes you've been talking. There's no official scoreboard, thank heaven.
Instead, consider whether the conversation is two-way. Does she offer stories without being dragged through a questionnaire? Ask about you? Return to topics that interested her? Seem comfortable enough to joke or disagree?
Most importantly, how do you feel? Are you enjoying her company, or concentrating so hard on making a good impression that you haven't noticed whether you actually get on?
Attraction isn't a prize awarded to the man who completes the conversation correctly. This is a chance for two people to make a mutual choice.
A wonderful first date might include a couple of clumsy moments. A very polished one might feel oddly empty. Pay attention to warmth, interest and the ease of being yourselves rather than seeking a flawless performance.
Finish with clarity, not another interview question
The bill comes. You step outside. There's that familiar awkward moment where both people wonder whether to linger.
If you've enjoyed the evening and would like another, say so. “I had a really lovely time with you. I'd like to see you again.” Clear, straightforward and rather refreshing.
You can suggest a specific idea once you've both established that another date sounds good. Perhaps she mentioned a favourite gallery or a place she'd like to visit. Remembering it gives your invitation a personal touch.
If she doesn't feel the same way, accept that without pressing. Not every pleasant evening has to become a love affair, and there is nothing undignified about two people discovering they aren't quite a match.
And if you've enjoyed yourself but you're unsure? You are allowed to think. A first date isn't a compulsory referendum before the taxi arrives.
A final word from Monty
The best first-date conversation isn't the one with the most impressive questions. It's the one where both people feel heard, discover something unexpected and have enough fun to forget they're supposed to be making an impression.
Start with what's in front of you. Ask about the things she cares about. Tell her things about yourself. Follow an interesting answer instead of moving mechanically to the next subject. Let the serious moments and silly moments take their turns.
You do not need to leave the restaurant knowing her five-year plan.
Knowing whether she makes you laugh, whether you're curious to hear more, and whether she'd like to see you again—that's quite enough for one evening.