If you feel inexperienced at dating in your thirties, start with straightforward invitations, choose dates where you can talk comfortably, and be honest about your history when it's relevant without making it your entire personality. You can learn what you enjoy, communicate your pace and ask questions as you go. You don't need an impressive romantic résumé, invented former girlfriends or a secret handbook for people who supposedly mastered dating at nineteen. What matters now is how you treat the woman you're meeting and whether you genuinely like each other.
Allow me to present the case of a gentleman aged thirty-four who is quite competent at life.
He manages a workshop, pays his bills, cooks a sensational Sunday lunch and once repaired his sister's kitchen ceiling while everyone else offered advice from a safe distance. Yet the prospect of going on a first date makes him feel as if the world has entered an examination season he didn't know existed.
His name, for our purposes, is Edwin.
He has been to a couple of social gatherings with women he fancied, but he's never had a long relationship and hasn't been on many proper dates. Now a lovely woman has agreed to meet him at an independent cinema. He's delighted—and worried she'll somehow detect his lack of experience from the way he buys tickets.
I have terrific news for Edwin. Cinema tickets come with no section marked previous romantic achievements. Let's deal with the evening he's actually about to have.
There's no compulsory dating timetable
By your thirties, the people around you may be married, divorced, living with partners, newly single or happily unattached.
A few have dated constantly. Others spent their twenties working, caring for family, studying, recovering from a difficult period or simply not meeting anyone they wanted to date.
Some people have never been in a relationship, and that history can have all sorts of perfectly ordinary explanations.
You're not required to provide a written defence.
Don't assume that the woman opposite you has reached every milestone either. Her romantic history is her own. She may have been in relationships for years or may have had fewer dates than you've imagined.
You can find out what you both want now without comparing imaginary scores from the past.
The only timeline of immediate interest is whether you're meeting on Friday and whether the cinema actually starts at half past seven.
Don't invent a history to sound experienced
Here is a dreadful plan: Edwin decides to mention a fictional ex-girlfriend named Samantha.
Samantha is glamorous, conveniently abroad and supposedly taught him everything about romantic sophistication. Within twenty minutes the woman he's dating asks whether Samantha liked the same kind of films.
Edwin now has to remember a woman who does not exist, her opinions on cinema and apparently her passport details.
This is not a promising beginning.
If somebody asks directly about your experience, answer truthfully and without performing shame. “I haven't done much dating, actually. Life took me in other directions for a while, but I'm enjoying meeting people now.”
That's a perfectly adult answer.
You aren't obliged to volunteer an account of every relationship you've never had in the first five minutes. But don't lie when the subject naturally arises.
The woman may be curious. She may have questions. She may not care much at all. Let her respond as an individual rather than deciding in advance that she must think badly of you.
How much should you reveal on a first date?
There's a difference between honesty and turning dinner into a press conference on your personal history.
If she asks, “How long have you been single?” you can answer simply.
“I've been on my own for quite a while. I haven't dated much, though I do want to find someone I get along with.”
If she asks why, say what you're comfortable sharing. “I was focused on work,” or “I haven't met many people I wanted to pursue something with,” may be true for you. Use your actual reasons, not examples borrowed from a website.
Then return the conversation to the woman and the connection you're discovering.
You needn't apologise for the answer or ask for reassurance that she still considers you eligible.
Similarly, don't pretend to be a confirmed bachelor who wants nothing serious if you actually hope for a loving relationship.
The most appealing honesty is calm enough to let the conversation move forward.
Your first few dates needn't be elaborate
Edwin looks at photographs of rooftop restaurants, luxury hotels and couples drinking champagne from glasses shaped like laboratory equipment.
He assumes that's what a date in his thirties must look like.
Utter nonsense.
Choose somewhere where you're both comfortable talking: a café with a decent atmosphere, a small exhibition, a relaxed pub, a market followed by lunch or that independent cinema with a drink afterwards.
A first date is an opportunity to find out whether you enjoy someone's company, not a ceremony designed to justify three years of annual leave.
Make the invitation clear and specific. “There's a film on Friday that I think we'd both enjoy. Fancy going together and getting a drink afterwards?”
Confirm arrangements. Arrive on time. Look tidy. Listen to her.
None of this requires a history of previous partners. It requires the same consideration you'd bring to meeting anybody whose company you value, with the delightful additional possibility of romance.
What to talk about when you haven't got dating stories
Some men fear that a woman will expect a fascinating collection of stories about former lovers, extraordinary proposals and romantic holidays.
In reality, you'll have plenty to talk about that isn't a catalogue of relationships.
What's she passionate about? What has she been looking forward to lately? Where does she like spending a free Saturday? What made her choose her work? What ridiculous thing happened on her last holiday?
Share your own life. Edwin might tell her about repairing the ceiling. There's a difference between describing every nail and telling the colourful bit: the moment his sister's Labrador wandered underneath with a stolen paintbrush.
A decent anecdote, a curious question and a little humour are more useful than pretending to have dated women on four continents.
If she talks about her past relationship, listen without treating the ex as your invisible opponent. You can discuss experiences without being compared against them.
People date to discover the person across the table, not to review a league table of their former romances.
You can flirt without pretending to know every move
Perhaps you've watched videos in which men apparently seduce women by deploying the correct combination of eye contact, compliments and strategic pauses.
The result can be a man so busy conducting a technique that he forgets to enjoy the woman he's talking with.
Start with what feels genuine.
If she tells a witty story, laugh. If you like her taste in music, say so. If you enjoy the way she sees the world, offer a sincere compliment.
“I've had such a good time talking to you.”
That's romantic interest expressed in plain language, not a high-risk manoeuvre.
If she responds warmly, you may exchange a little playful teasing. If not, leave the tone where she's comfortable. Don't interpret every smile as permission to touch her.
When you want to arrange another date, ask directly instead of waiting for an elusive signal that success is guaranteed.
Charm is not measured in previous attempts. Often it is simply the pleasure of being genuinely present.
Dating and physical affection at your own pace
One of Edwin's biggest private worries is that a date might lead to a kiss, and he'll look inexperienced.
But physical affection isn't a race or a test of technical sophistication.
You and the woman you're seeing are allowed to take things at whatever pace feels comfortable for both of you. She might want a kiss; she might not. You might want to wait. None of those possibilities requires embarrassment.
If you're unsure whether a kiss would be welcome, you can ask. “I'd really like to kiss you. Would you like that?”
That isn't an admission of incompetence. It's direct and considerate.
And if the relationship develops further, talk honestly about what each of you enjoys, wants and doesn't want. Ask rather than assuming everybody has the same preferences.
You don't need to bluff your way through experiences that are new to you. Real intimacy gives two people room to communicate.
An experienced man who ignores what a partner wants is not magically better company than an inexperienced man who listens.
Don't turn her into an instructor
There's a tempting opposite mistake: expecting the woman you're dating to explain every aspect of courtship.
“Should I text tomorrow? Is this how a date usually works? Have I done this properly? What happens next?”
A little openness is delightful. Requiring her to assess every decision is exhausting.
You can suggest the restaurant, choose a time that works and communicate what you'd like. If a detail matters to her, you can discuss it.
She's a person with her own wishes, not the headmistress of a boarding school for late-blooming gentlemen.
And remember that even people who've dated for years cannot read minds. They still have to ask what the other person wants. Experience doesn't remove uncertainty; it simply means someone has encountered it before.
Treat her as an equal participant. Offer your judgement as well as your curiosity.
When she has much more experience than you
Suppose she tells you she was married for eight years or has dated quite extensively.
You needn't feel compelled to make the numbers match.
She may know more about what she wants in a relationship, or she may still be discovering that. You can listen and tell her what you want.
If she hopes to settle down and have children, that's useful information to discuss honestly when appropriate. If she wants something casual and you don't, say so.
Don't accept a relationship arrangement merely because you're grateful that somebody is interested in you.
There's no need to admire her past partners, compete with them or interrogate what they did better. Your current relationship will be formed by what the two of you choose.
The real question isn't whether your histories are symmetrical. It's whether your present aims, values and enjoyment of one another can work together.
When the first date doesn't lead to another
Edwin may enjoy the cinema and discover the woman doesn't want a second date.
That will disappoint him. It won't reveal that he's failed a special examination for men in their thirties.
If he made a specific mistake—talked over her, ignored a question, forgot an arrangement—he can put that right next time.
But a lack of chemistry isn't always a problem to be solved.
He can keep meeting people through events he enjoys, accept introductions and use dating apps if they suit him. He doesn't need to find a new partner by the end of the month or pretend every outing must lead somewhere.
Nor should he date women simply to acquire experience. The woman deserves genuine interest in her particular personality.
Romantic history is something that develops when people meet and enjoy one another. It isn't a certificate you can purchase before participating.
Edwin buys two cinema tickets
The woman arrives looking lovely. Edwin is almost certain that the clerk can tell he's inexperienced, but the clerk is occupied with a stubborn ticket printer and doesn't appear to care.
They watch the film. Afterwards she laughs at his theory about the ending. He tells her about the escaped Labrador and the paintbrush; she tells him about a disastrous holiday in Cornwall.
He does not mention the fictional Samantha. She never existed, and there is far too much genuinely interesting conversation to justify inventing her.
When they part, Edwin says, “I've had a wonderful evening. Would you fancy dinner next week?”
She considers it, then smiles and says she'd like that.
Perhaps they become a couple. Perhaps they discover other differences on a second date. But one thing is certain: Edwin has finally stopped treating his lack of a romantic résumé as a barrier to meeting someone.
If you're in your thirties and feeling inexperienced, bring the life you've actually lived, not a history you think a woman expects.
And if anyone asks for your dating qualifications at the cinema door, I shall personally have words with the management.