To start dating when you have no experience, decide what sort of relationship you're looking for, find one realistic way to meet women, introduce yourself honestly and invite someone you enjoy talking with on a simple first date. You don't need previous girlfriends, rehearsed chat-up lines or a complicated romantic history. Use honest photographs and information if you try a dating app, arrange a first meeting in a public place, take an interest in her as an individual and let things develop at a pace that suits you both.
Now, before we go any further, I should like to dismiss a thoroughly ridiculous notion: that everyone else was born knowing how to date.
They weren't.
Some men begin courting at sixteen. Some start at twenty-six, forty-six or considerably later. Some have spent years concentrating on work, family, illness, travel or simply other things.
The trick is to begin without turning your lack of experience into the headline of your entire personality.
A man may be capable of running a household, learning a trade or supporting his friends while still feeling inexperienced at asking a woman out. That's not a contradiction. The first date is new territory, but you can approach it with the same consideration you bring to other parts of your life. You don't need an initiation ceremony. You need an opportunity to meet somebody you genuinely like and a willingness to make a simple invitation.
“How does one begin?” he asked.
Decide what you want before opening an app
You don't need a detailed blueprint for the next decade, but having some sense of what you're hoping to find makes dating easier.
Would you like a committed relationship? Are you open to meeting somebody and seeing whether you click? Do you prefer a slow introduction before romantic expectations develop?
There isn't one answer everybody must give. What matters is that you don't pretend to want something you don't, merely to attract someone.
If you're looking for a serious relationship, say so in the appropriate setting. If you're unsure, you can be honest about that too, provided you don't give someone misleading promises.
Dating apps often let you indicate your intentions. Social events may make expectations clearer through their format. Someone you meet through mutual friends may require a little more conversation before either of you knows whether romance is on the cards.
The aim is to meet women who are free to make an informed choice about whether they'd like to get to know you.
Where to meet women when you've never dated before
There are plenty of possibilities: dating apps, introductions from friends, singles events, hobby groups, community gatherings and the ordinary encounters that happen when you're out enjoying your life.
You don't need to do all of them.
Pick a route that seems manageable and suits the kind of person you hope to meet.
If you like organised social situations, a singles event with activities may be less daunting than approaching strangers in a packed bar. If you're comfortable writing a few messages before meeting, a dating app might suit you. If you have friends who enjoy hosting dinners, ask whether they'd introduce you to someone they think you'd get along with.
The last option isn't a request that friends produce a girlfriend on demand. It's a polite willingness to meet new people.
If a friend hosts regular gatherings, you may already have opportunities to meet people in a relaxed setting. Join in because you enjoy the company, rather than treating every occasion as a hunt for a date.
We began there. No yacht required.
Make a dating profile that represents the real you
If you use an app, start with photographs that actually look like you.
A clear picture of your face and a couple of recent images showing something of your ordinary life are better than a gallery of filtered mystery portraits. Avoid making it impossible for a woman to work out which man you are in a group photograph.
Give her a few details that make conversation possible.
“I work in engineering, enjoy restoring old radios and have an unreasonable weakness for seaside fish and chips” is more informative than “Just ask”.
You can mention what you're hoping to find without turning the bio into a list of demands. A warm, specific line is more inviting than a noticeboard headed NO DRAMA.
Don't claim hobbies you don't have or borrow somebody else's expensive car for an illusion of glamour. If she likes you, you'd rather she liked the person who actually turns up.
Start conversations by noticing something real
When you match with a woman, don't spend three days searching for a magical opening line.
Read what she's written and respond to something specific.
She enjoys hiking? “That photograph by the lake looks fantastic. Where was it taken?”
She loves Italian food? “I've been looking for somewhere good for pasta. Have you found a place worth travelling for?”
She mentions a particular book? Ask what she thought of it, if you're genuinely interested.
If you meet in person, the same principle applies. Talk about the situation you're sharing instead of delivering a memorised performance.
If she doesn't seem interested, don't keep pushing. Not every conversation will become an invitation.
How do you know when to ask her out?
Look for a conversation in which both of you are participating.
Does she answer with some enthusiasm, ask you questions and seem happy to keep talking? You may have enough of a connection to suggest meeting. You don't need weeks of correspondence before making the invitation, though some people prefer more time or an initial call.
Be straightforward.
“Your story about the coast made me smile. Would you fancy meeting for coffee on Saturday?”
That's an invitation, not a contract. If she'd rather continue chatting for a while, respect that. If she declines, accept her answer.
Choose a venue that's easy to find, public and comfortable to leave. Avoid spending a fortune on a first meeting. You're getting to know a person, not staging the opening night of a West End production.
You are meeting another person, old boy, not negotiating a royal marriage.
He booked a small café instead. His bank manager remained blissfully unaware of the romance.
What happens on your first date?
Arrive on time, greet her warmly and put your phone away.
If you're unsure whether a handshake, hug or other greeting would be welcome, follow her cues or simply ask. You're not required to guess correctly about physical contact.
Start with ordinary conversation. You already know something about her from the messages or the circumstances in which you met. Pick up a thread.
“You mentioned you were going to York last weekend. How was it?”
Then listen. When she answers, respond to the actual detail rather than racing through a checklist of prepared questions.
Tell her things about yourself too. A date should feel like an exchange, not an interview conducted by a man who has memorised an application form.
You can compliment her if it feels natural. You can laugh at something amusing. You can say when you're enjoying the evening. You don't need to manufacture confidence by bragging or speaking over her.
And notice how you feel. It's not solely a test of whether she likes you.
The things beginners worry about unnecessarily
Most of these decisions become easier when you stop trying to achieve a perfect performance.
Order food you actually enjoy and can comfortably eat. Ask questions because you're curious. If there's a quiet moment, let it pass. If you mishear a word, ask her to repeat it.
You don't need to kiss her at the end of a first date. You don't need to avoid kissing her according to somebody else's arbitrary timetable either. Any physical affection should be clearly welcome to both of you.
You also don't need to pretend you have previous dating stories. If an appropriate moment arises and she asks about your past, you can say, “I haven't dated very much, actually. Other things have taken my attention, but I'd like to meet someone now.”
That's a normal answer. Not an apology, not a confession, and certainly not the opening of a three-volume autobiography.
Should you tell her you've never dated before?
Answer honestly at a level of detail that suits the stage you're at.
Perhaps you've concentrated on work or family. Perhaps you had little interest in dating until recently. Perhaps you simply never met somebody you felt ready to pursue.
“I spent a long time focused on my career and didn't make much time for dating. I'm interested in changing that now” tells her what she needs to know.
You don't have to invent ex-girlfriends to seem experienced. That lie will only leave you remembering details about imaginary holidays.
If she decides inexperience doesn't suit her, that's her choice. You don't need to persuade her that a different history would have made you more worthy.
Who pays on a first date, and how do you say goodbye?
Ah, the apparently complicated business of ending an enjoyable evening.
There is no universal rule that a man must pay for everything. You can offer to cover the coffee or meal if you wish, but respect her preference if she'd rather split the bill.
A gesture freely offered is rather nicer than one presented with a secret expectation of affection in return.
If you've enjoyed the date, say so before leaving: “I've had a really nice afternoon. I'd be glad to see you again.”
She may feel the same way, may want time to think or may decline. Don't try to read the outcome from whether she adjusts her coat before leaving.
When you part, respect personal space and don't assume a kiss is owed because the evening went well.
If you'd like to follow up, a friendly message later is perfectly sufficient. You don't need to wait three days to appear mysterious. Nor must you send nine consecutive updates about the weather.
What if the first woman you ask says no?
Then you've had your first experience of something that happens to experienced daters too.
It's disappointing, perhaps embarrassing, but it isn't evidence that you should have started years earlier.
You may have misjudged mutual interest, or she may simply not fancy you. She is entitled to choose. You are entitled to try again with someone else when you feel like it.
Learn any useful lesson, such as making your invitation clearer or choosing a better time. But resist constructing an entire theory of what women want from one person's answer.
Equally, if the date was pleasant but you didn't feel attracted to her, you don't owe another outing. Be kind and clear rather than keeping her interested out of politeness.
Make a simple invitation and see what happens
Suppose you've enjoyed talking with a woman at a friend's gathering. You could say, 'I've enjoyed meeting you. Would you fancy coffee next weekend?' If she accepts, make a practical plan, arrive on time and give the conversation your attention. If she declines, acknowledge it and continue with your life. A first date may lead to another or may simply teach you that you can handle meeting somebody new. The useful progress comes from taking an honest step, not from acquiring a perfect story to tell afterwards.
She agreed.
Your first step begins before your first date
If you've never dated, pick one small action that moves you towards meeting women.
Set up an honest profile. Find a social event you'd actually enjoy. Tell a trusted friend you'd be open to an introduction. If you're already talking to a woman and the interest seems mutual, suggest a simple coffee.
That's enough for a start. You don't have to complete an entire romantic career by Thursday.
And for a taste of Monty's methods before your first proper invitation, 7 Secrets to Becoming a Babe Magnet is the free 14-page guide featured here. No invented girlfriends required.
Welcome to dating, old boy. There is no entrance exam, and the champagne is optional.