It’s a weird time to be a gentleman on the dating scene — or at least so I’m told. Mating rituals once conducted over a tall drink, on a date set up by a friend of a friend no longer run the game. Instead, the social hubs of the city are illuminated by a ghostly blue glow, thrumming with the pulses of fingertips pressing, swiping and tapping their way into pseudo-intimate connections.
And, thanks to this technological revolution, something as simple as sending a drink to a stranger across a bar has become a phenomenon reserved for scenes in James Bond movies and Mills & Boon novels. To this, we say more’s the pity. Sure, Tinder is great for the person seeking a flight of fancy (see also: a quicker route), but a true gentleman loves a challenge.
With this in mind, we have curated a failsafe, step-by-step guide for sending a drink over to a stranger at the bar — without falling into the trap of becoming at best quaint, or at worst downright creepy.
1. Assess the situation
Like any intrepid explorer in the wilderness, survival in a crowded city bar will rely on your sharpened instincts and keen assessment of the environment.
Once you’ve spied the person you’d like to make the first move with, assess the situation. If they are clearly otherwise engaged, bide your time. If they are already on their way to being on the wrong side of tispy, then they are no longer a viable option.
And if they’re already clearly on a date? Best to back away slowly.
2. Eye contact
They are the window to the soul and, more importantly, can be used to make a more graceful signal than an ill-advised thumbs-up when the recipient turns to discover their benefactor.
Eye contact signals confidence, genuine interest and offers a chance to better survey how your gift has been received to plan your next move.
3. Decide on a drink
Show that you’re attentive by ordering another round of what they already clearly enjoy. (Perhaps allowing for an exception if their last round was a night-starting double shot).
If they clearly are not drinking alcohol, don’t be perturbed; just send something booze-free but still interesting.
4. Subtly order
Nobody likes a show-off, and a gentleman who makes a song and dance out of ordering for a stranger runs a seriously high risk of seeming arrogant or, (worse) as though he is taking part in a Stag-Do dare.
Similarly, make your motives too clear and the person you are buying for will cotton on to your intentions, somewhat ruining the surprise.
Stay calm and collected as you request the order, and let the barman take care of the rest.
5. Keep your cool
Ask the bartender to point you out upon delivery, before offering an understated acknowledgment — a small wave will suffice, as will a small toast of your own drink.
Don’t be put off if you aren’t instantly offered a beaming, grateful smile from across the bar — your recipient is likely to be a little confused at first.
You’ve made your super-suave move now, so the time has come for a friendly smile. Try not to over think it, just glance over and smile as if you’ve seen someone you recognise.
Avoid any further signals at this point, to ensure you aren’t coming on a little too strong.
7. Confidently approach
This step comes with the disclaimer: do not approach a person at the bar who has offered you no signal that they are interested in the exchange going any further.
If, however, they seem keen to get to know their mysterious benefactor, then walk over ready with a few opening lines and do not succumb to the fear you might be making a mistake — it’s too late to run back now.
8. No chat up lines
9. Order another
If you have followed all these steps diligently, made your way to the other side of the bar and entered into a delightful, free-flowing conversation then it’s time to make the next step.
The key here is to offer another drink before ordering “another round over here”. This will allow your companion to politely say no without feeling under too much pressure. It might also mean that they offer to pay for the next one, which might be a more comfortable exchange for them.
10. Know when to quit
This piece of advice relies on you having a pretty accurate radar when it comes to reading the signals of the person sat across from you. As a basic rule, if they’re repeatedly checking their phone, regularly scanning to room, or making vague, abstract excuses for taking their leave, then it’s time to cut your losses and say a polite goodbye.
There’s always next Friday night.
Looking for more etiquette advice? Here are 10 ways to make yourself more charismatic…