THE JOURNAL

The best flirt I have ever experienced happened in a Starbucks, where a guy with a nice beard leaned over and said, in a very stern tone: “Leave some Splendas for everyone else.” I looked up, startled to be admonished by a stranger and his eyes were, well, twinkling. To be clear, I had just poured four Splendas into a 20oz coffee because I was a new coffee drinker and had to make it taste as much like a dessert as possible. (Four years later, I can tell you that I’m down to a very mature three Splendas.) Anyway, the guy with a good beard and I went on three or four dates, and, while I ultimately didn’t feel anything for him, his flirting skills remain unmatched. He had what might be called – in a movie review or write up of his personality – charm.
Much has been made of how difficult it is to flirt “these days”. Do not listen to the people who say this: they cannot tell the difference between making someone feel uncomfortable and having a good time. But you can. Let’s first define what successful flirting is and what it isn’t. Flirting is not pressuring someone to get into bed with you or incanting some magic words to make yourself seem attractive to someone who would otherwise overlook you.
Flirting is having an attraction-tinged interaction with someone who is already open to talking to you. Flirting is mutual, playful and light. Flirting, at its core, is about expressing interest in another person, and while usually that interest is sexual, it doesn’t have to be. Successful flirting will not get you into bed with someone who never wanted to be there in the first place (that is a creepy goal in and of itself), rather it is a way of treating someone whom you respect with a bit more fun.
According to Dr David Dryden Henningsen, a professor at Northern Illinois University, there are six reasons we flirt: to get someone into bed; simply for the fun of it; to increase self-esteem; to see what it would be like to be in a relationship with that person; to advance a relationship with a person; and to try to get something from someone. This wide spectrum accounts for why some flirting can feel harmless, while some can seem transactional. Therefore, there are places and times where serious flirting is simply not appropriate. Being teasing and friendly with a bartender is one thing, but being overtly sexual with your assistant at after-work team drinks is not OK. Neither is flirting at a funeral (should go without saying, and yet…), or with someone who is already taken. Flirt for the love of the game, not for the score. (This is not meant to be confused with Mr Neil Strauss’ Rules Of The Game, which contends that women are to be dismissed, degraded and manipulated into wanting to date you; the premise of which is as ineffective as it is insulting).
Nota bene: basic kindness is not very effective as a flirt. Holding the door for someone, offering to water their plants when they’re out of town, giving them a ride if their car breaks down? Those things are simple kindnesses, they aren’t playful. Flirting is an invitation to have extra, perhaps suggestive fun in an interaction. Someone can decline said invitation, but the idea is to increase the fun, not to simply be a nice pal and hope that someone notices and appreciates that.
Below, some tips and ground rules for how to have a little fun as we approach the season of holiday parties. Take a look and then go forth: flirt like you mean it. Hopefully you’ll meet someone nice in the process.
01.
Engage
The keys to being able to flirt with someone well are to listen and respond to what they’re saying. If you’re simply waiting your turn to talk, that is not listening. (This is a good general life tip.) If you correct them, talk over them or dismiss what they’re saying, I can guarantee you will not be inspiring mutual attraction.
One of the easiest ways to make sure that you’re helping to carry the conversation is to ask questions. If someone asks you a question, answer and then follow up with “And what about you?” where appropriate. Even better, get them talking about what they do or love or want – anything that might inspire passion or excitement – and then keep asking questions to find out more.
Caveat: this must come from genuine curiosity. You cannot ask your way into someone’s heart. There is not a magical number of times you pose a question that makes you attractive, it’s simply the right way to converse with people – and one men often overlook. If you aren’t genuinely interested in what a person has to say, you ought not to be flirting with them at all.
02.
Tease
The sine qua non of flirting is its lack of seriousness, therefore teasing does a lot of the heavy lifting. Of course, you don’t want to be picking on someone or belittling them – that is not sexy or romantic, that’s mean. Almost all flirtation involves joyful humour. Obviously, do not tease people about their appearance or how they laugh or their background. Have fun with what is happening in the moment. Tease yourself. Make yourself the butt of the joke without being too self-deprecating. The point of teasing is to keep things light and to demonstrate that you’re a fun person to hang around. It’s not to position yourself as better or cleverer than anyone.
03.
Invite
Flirting is meant to bring people together, to invite them to the fun. (In this situation, you are the fun.) What you’re aiming to give off is an air of openness and inclusivity. You don’t want to seem brooding or closed off, despite what “pick-up artist” manuals peddle. Challenging what people say, staying silent or appearing disapproving are all great ways to be precisely zero fun; people want to go home with someone who seems like a good time. You want to be the man who makes people want the night to last longer, who makes people wish the bar was open later.
04.
Enjoy
Remember that you ought to be having a good time, as much as the other person. Flirting isn’t meant to trick them or present yourself as someone you’re not. It’s the encouragement of an attraction via fun. And you should be in on the fun, too.
Illustration by Mr Michael Parkin