To stop feeling awkward on dates, choose a setting where conversation can happen naturally, stop trying to fill every silence, and treat the woman opposite you as a person you're curious about rather than someone you're performing for. Ask a question, listen to her answer, share something of your own and let the conversation develop. A little nervousness or an occasional clumsy moment is normal. The goal isn't to become flawlessly smooth; it's to make spending time together easier and more enjoyable.
There is a certain fellow who goes on a first date as though he's attending an interview for an extremely lucrative position.
He arrives polished, prepared and already perspiring at the thought of a follow-up question. He has memorised three amusing stories, two compliments and the correct moment at which to ask about siblings.
By dessert, the poor woman has provided her employment history, favourite holiday destination and thoughts on early childhood. She still hasn't seen the slightest glimpse of whether the man himself knows how to have a good time.
An acquaintance of mine named Martin was an accomplished specimen.
Martin had a dreadful habit of arranging his dates with the precision of a military parade. At precisely seven he'd ask about work. Seven-fifteen was devoted to hobbies. By half-past seven he was supposed to have made one lighthearted remark about travel.
“I don't think I'm very good at dating,” he told me.
“My dear Martin,” I replied, “you aren't dating. You're conducting a very polite census.”
Let's begin by taking the clipboard out of his hands.
Why some dates feel awkward even when nobody does anything wrong
Sometimes there's simply no romantic connection. Two decent people can sit through a pleasant dinner and discover that their conversation doesn't flow. You cannot manufacture chemistry by rearranging the cutlery.
But awkwardness can also come from the structure of the meeting. A noisy venue makes listening difficult. Sitting opposite someone in complete silence feels more intense when the only thing to look at is a candle. An expensive dinner creates a sense that the evening must justify its price.
And sometimes the problem is self-conscious performance. You become so busy thinking about your next sentence that you stop noticing hers.
The easiest improvements are practical: pick a suitable place, allow a natural shared activity, and stop viewing every minute as an examination.
For a first meeting, coffee and a short walk somewhere public may feel more relaxed than a formal three-course meal. A gallery or daytime market can give you things to talk about without forcing continuous eye contact across a small table.
Arrive with curiosity, not a list of interrogation questions
It's fine to have an idea or two in mind. You might want to ask how she got into her profession, what she does at weekends or what she thinks of the place you've chosen.
But don't treat the conversation as a questionnaire.
Suppose she says she enjoys cooking. Instead of rapidly moving to “Have you got brothers or sisters?”, stay with her answer.
“What do you love making?”
She says she's been learning to make pasta.
“That's ambitious. I usually congratulate myself if the sauce survives.”
Now she has room to laugh, share a story or ask what you enjoy cooking.
One subject may lead to three others, and none of them needs to appear on a prepared list.
In genuinely enjoyable conversation, questions and observations move back and forth. If you're the only person asking, notice that too. A date should involve two willing participants.
Give the silence somewhere to go
You will encounter a pause. Perhaps the waiter arrives. Perhaps you've finished a topic. Perhaps she's thinking.
Don't panic and announce a second question before she's had time to answer the first.
Look around. Comment on something genuinely interesting. Take a sip of your drink. Let the next thought arrive.
A brief quiet moment can be perfectly comfortable if you aren't treating it as a disaster.
If the conversation has really stalled, try returning to something she mentioned: “You said earlier you've just moved here. How are you finding it?”
Or share a little story of your own, preferably a short one she can join.
“Have you ever been to a restaurant where the waiter seems furious that customers have turned up? I encountered one last week.”
A story with a simple opening gives her something to respond to. Twenty minutes about the history of the establishment does not.
Do something together instead of constantly facing each other
Martin's first breakthrough happened at a Saturday antiques market.
He'd planned to meet a woman named Anna for coffee, but the café had a queue stretching into the next county. So they walked through the market while waiting.
They debated an enormous brass lamp that looked rather like a piece of machinery removed from a submarine. Anna found a stall selling old postcards. Martin discovered an antique telephone and insisted on testing its weight, as though he were considering making a very long-distance call to 1924.
They were suddenly laughing and talking without struggling to invent topics.
The market provided conversation material. It also gave them permission to move, stop, observe and share impressions.
That's why an activity can help. It mustn't be so complicated that you can't talk, and it shouldn't trap either of you for hours. Keep it accessible and agree on something you're both interested in.
Stop checking whether you're being attractive every thirty seconds
Here's one of the less glamorous truths about romance: worrying constantly about how you're coming across can prevent you from actually engaging with the woman in front of you.
You miss the end of her story because you're assessing whether your previous joke sounded clever. You don't ask a follow-up because you're trying to remember the next part of your script.
Instead, pay attention to what you're enjoying.
Is she interesting? Do you like her sense of humour? Are you comfortable with the way she treats you? Would you enjoy seeing her again?
These questions matter just as much as whether she likes your shirt.
If you notice yourself slipping into performance mode, return to the conversation. Ask about a detail she mentioned. Respond honestly to what she's said. Allow yourself to be interested rather than constantly impressive.
A date isn't a talent show in which the judges conceal their scorecards until dessert.
Give answers that offer something back
Awkward exchanges often happen because someone gives answers that leave no opening.
“What do you enjoy doing?”
“Football.”
“Oh. Who do you support?”
“Liverpool.”
“Right.”
Now she must work again to keep things moving.
There's nothing wrong with being a football supporter, naturally. But a slightly fuller answer helps.
“I support Liverpool, so my weekends can be rather emotional. I also love getting out for a walk when there's no match on. Are you into football at all?”
You've offered a glimpse of your personality and invited her to share hers.
Do the same when she speaks. Acknowledge her answer, show curiosity and volunteer your own view. Not every response needs a witty punchline.
If she asks what you enjoy about your work, don't merely state your job title. Tell her something about the part you find satisfying or the characters you meet.
Conversation becomes easier when neither person has to drag every detail out of the other.
Flirting can be small and unmistakably human
There's an extraordinary amount of rubbish written about the precise number of seconds a man should maintain eye contact before a woman falls helplessly in love.
Monty declines to operate with a stopwatch.
If you fancy her, show a little warmth. Smile at a shared joke. Notice something distinctive about her. Tell her you're enjoying her company.
“You're very funny. I hadn't expected to spend so long discussing antique telephones.”
It's a compliment with context, and it doesn't place pressure on her to respond romantically.
A little teasing may be welcome if she is clearly playing along. If she isn't, don't repeat it or increase the intensity.
The point is to let a date become a little flirtatious if both people enjoy it, not to force the transformation at a prearranged minute.
Stop overmanaging the little practical details
He spends fifteen minutes apologising for the table. He asks whether the temperature is acceptable every three minutes. He consults a map to ensure their walk is precisely one mile long.
It can become exhausting for both of them.
Make sensible plans, of course. Know where you're going. Check that the venue is open. Give her a choice where appropriate.
But once you've arrived, let the evening happen.
If the café is full, suggest the one round the corner. If it starts raining, find somewhere dry. If your original plan isn't working, ask whether she'd prefer something else.
Being adaptable can be much more enjoyable than rigidly defending the itinerary.
When Martin stopped trying to manage every minute, Anna had the chance to suggest the places she wanted to see. The date improved immediately.
Know when an awkward feeling is telling you something useful
Not all awkwardness is a problem you must fix.
Maybe she's giving one-word answers and making no effort to talk. Maybe you have little in common. Maybe she keeps making jokes at your expense and you don't find them funny.
You may simply not be well matched.
You can try changing the subject or inviting her to share something she enjoys. But you're not responsible for single-handedly producing the evening's entertainment.
If either of you is uncomfortable, respect that. A date can end politely without a dramatic explanation.
“I think I'll head off now. Thanks for meeting me.”
There's no reason to extend a connection that clearly isn't working.
And if you're genuinely interested but she isn't, accept her answer. Being relaxed on dates doesn't mean being able to change someone else's mind.
How to end a date without making the goodbye an ordeal
For some men the last ten minutes are the most uncomfortable of all.
Should you kiss her? Hug her? Say you'll call? Ask for another date immediately? Stand by the car for half an hour discussing whether either of you has an early start?
There's no compulsory choreography.
If you've had a good time, say so: “I really enjoyed today. Would you fancy meeting again?”
If she's enthusiastic, you can make a plan. If she's unsure, let her decide. If she declines, be gracious.
Don't assume physical affection is expected. Follow what is clearly welcome and ask if you're uncertain.
You can leave on a lovely note without creating an elaborate closing ceremony. Sometimes “It was great meeting you” and a warm smile are precisely what the moment needs.
Afterwards, a short, genuine follow-up can be appropriate if you'd like to see her again. No formula about waiting several days is required.
Martin discovers an entirely different dating method
By the time Martin and Anna reached the end of the antiques market, they'd forgotten half their original plan.
They'd bought nothing but two coffees and a postcard showing a seaside town neither of them recognised. They'd disagreed over the merits of a hideous ceramic duck. They'd laughed at an old telephone whose receiver weighed roughly as much as a brick.
Martin hadn't delivered his three prepared anecdotes. He hadn't checked his watch once to see whether he was on schedule.
When he asked Anna whether she'd like to see him again, it sounded like a natural continuation of an enjoyable afternoon.
She said yes.
That doesn't mean every market outing will end romantically. What it shows is that awkwardness often fades when you stop trying to control the encounter and start taking part in it.
The point of a date is the other person
You can make a date easier with a well-chosen venue, genuine questions, relaxed pauses and a little honest flirtation.
But don't become so fixated on being smooth that you lose sight of the woman herself.
Look at her. Listen to what she says. Let her surprise you. Be willing to discover that you like her enormously, or that you're both perfectly nice people who would be better off meeting somebody else.
That's the difference between dating and giving a performance.
And if you want Monty's help making that first meeting a little more charming, my complimentary Babe Magnet introduction is yours through the free-guide offer on this page.
Put the imaginary clipboard down, old boy. Ask her what she thinks of the hideous duck.