Tuesday, March 5, 2013

Haven't We Met? You're Some Kind of Beautiful Stranger: A Guide to Flirting

It’s happened to (almost) everyone, you’re at a party/bar/coffee shop and you see an attractive stranger, one that you want to talk to. Maybe you can’t explain why, chances are that you see attractive people all the time but every once in a while, someone is different in that you decide you want to approach them. So you do and you walk away from the conversation either wanting to see them again or knowing that you probably won’t, but either way you did it. You flirted with a stranger. (This can also apply to someone that you have seen around but don’t really know)

Let me state that I don’t believe I am at all qualified to write this post. When it comes to flirting with someone I am interested in, I am rendered incapable. I become shy. I am the queen of awkward. I blurt out the most random and often counter productive things including but not limited to: “Your shirt is blue” or my personal favorite, “You seem like a player.” (cringe) For some reason, I have no problem walking into a networking event and engaging with new faces but when it comes to that cute guy across the room I can’t bring myself to do it. Maybe this is because in a work or friendly capacity, I know where I stand and what’s at stake, but when an undefined element enters the picture I’m thrown off my game. The truth is, walking up to a stranger/someone you don’t know very well and trying to flirt with them is pretty scary, no matter who you are. The main reason being that rejection isn’t fun regardless of how healthy your self esteem might be.

So when it came to writing this post, I sent out a mass email to friends, both male and female, some and attached some single and asked them for their expertise in this rather daunting forum. Some responses made me laugh, some made me cringe, but for the most part, I was surprised to find that very few had an exact methodology or approach to how to pick someone up. 

I also was told that the concept of picking someone up based on attractiveness is shallow, and to a degree it is. However, I think we need to be honest that-in addition to the personality aspect- we tend to engage in romantic relationships with people that we find physically attractive. And what each person finds attractive is different. (For instance, I don’t find Bradley Cooper or Ryan Gosling good looking but there are thousands who would disagree with me. However, Will Arnett...that's another story)

I’m digressing a bit. We’re talking about how to pick someone up and from my research I have determined some of the best approaches and some glaring no-no’s. (On a side note, this list is designed for approaches in which the goal is to get to know the person better, not just for the night:)


Smile. Sounds simple but appearing friendly and open is a big part of the battle. Furthermore, it might give the person you’re interest a reason to approach you, thereby saving you the work! I’m not suggesting to smile like a crazy person the whole time but try not to look bored or scowl.

HAVE FUN. Piggybacking on smiling, make sure you’re having fun! There is something intrinsically sexy about someone who is enjoying themselves and their surroundings. They have a sparkle and allure to them that people want to be a part of. Don’t spend your time worrying about whether the person you’ve been eyeing has noticed you yet, do your thing. The odds of getting positive attention from them increases if you’re having an awesome time with your friend vs standing alone impassively staring at them. (That just SOUNDS creepy, imagine what it looks like!)

Start a conversation. Some people are comfortable just walking up to someone but a lot of us aren’t. So for those who fall into the latter category: stand nearby, in a queue or something. Comment on something to them about the place, bbq, drink choice, anything really, as long as it isn’t negative. Get talking, Stand a little bit too close. Look rapt by everything they say, keep eye contact, laugh at their jokes. Say intelligent things. One thing that I HAVE learned over the years is that you can find common ground with anyone. The secret is finding what it is and building from there. One way to do this is by asking questions, actually listening to the replies and adding in if you can. If things go well, then all you need to do is work in a way to exchange information and see what happens from there.***please refer to the bottom for some tactic that I've seen work 

Have a wing(wo)man. No, this isn’t primary school and your friend shouldn’t go up and say, “My friend thinks you’re really hot,” that doesn’t work and nor should it. However, friends can be utilized in different ways. Let them make the initial approach/start the conversation, only to have you join in at some point. Flirting is really just an extended conversation, if the person likes you they'll continue talking to you, if they don’t, they'll stop. So then, you just move along and keep having fun with your friends. No harm, no foul.

Be yourself. Sounds pretty basic, right? However, when we’re trying to impress someone sometimes we get lost in the art of picking up and forget ourselves. While it’s normal to be a little bit nervous, it’s essential that we are comfortable enough with ourselves to be honest and realistic. The best conversations occur when we’re being natural, when we don't realize that we're flirting. If we don’t click with the person we’re interested in, then it’s best to move on anyway.

Be confident. We’ve talked about before that it’s sexy to be independent and confident, and it’s also sexy to not appear like it’s your goal to be picked up, because really it shouldn't be. (Your goal should be to enjoy yourself and your surroundings to go about your business as normal and see where the evening takes you.) One friend of mine just had an experience where she met a guy, had a great conversation and later on in the relationship they discussed how each one thought the other was picking them up. She wrote, “MAYBE the secret to picking someone up is actually believing you are the one being picked up. This could potentially go very wrong I suppose, but it probably does something to your confidence and thus your swagger and eventual success in the picking up. She’s right. You know your worth and what you have to offer, so it’s safe to assume that others see this as well and would want to pick you up.


Use pick up lines. They’re cheesy, they’re annoying, they show a lack of confidence and originality.

Latch on. Having a great conversation/flirtation session is great, but it doesn’t mean you’re attached at the hip for the rest of the night. If you are really confident you don’t spend all night talking to them, but smile, or catch their eye occasionally, - you are so popular and busy talking to everyone else. you can text them later or the next day. The chase is fun.

Be rude or insulting. Somewhere along the road, people got the notion that playing hard to get translated to being rude. Instead, bad manners are just obnoxious and a sure fire turn off.

Overindulge. Liquid courage is something many people rely on to generate initial momentum, but there is a limit. Falling down and slurring your words, hysteria or any overtly out of line behavior will only hinder, not help your cause. The only exception is on your birthday. Because everyone gets a birthday pass. 

Be creepy. Quirky and zany are good. Creepiness is not. A mild example came in a friends email, At the weekend I had a man point at my shoulder dimples and say ¨Do you know you have dimples there?¨, I was like...¨.....yeah¨, and then he stood and grinned manically at me.” This isn’t even that bad, there are many incredibly creepy and disturbing things that people say and do to garner attention, but it’s the wrong kind.

Lose sight of reality. The bad news is that not everyone we’re interested in is going to be interested in us. Sometimes, they won’t want to talk to us, sometimes they’ll decide after 10 minutes that we’re not their type. Sometimes they won’t ask for our phone number. This is kind of a blow to our ego but not the end of the world. It happens. Usually, it’s pretty obvious when someone is brushing us off, but we are too single minded to see it. Please, be objective, take the hints given, and gracefully make your exit while your dignity is still in tact.

Be desperate. Remember that thing called dignity that we just talked about? Try and hold on to yours. Nothing is more unattractive than being desperate. Except maybe being crazy and desperate. Or a crazy desperate stalker.

Let rejection get you down. This is just one person. Out of billions in the world. Just because they don’t want you doesn’t mean there is anything wrong with you. Sometimes people just aren’t compatible. Sometimes you’re just not their type. Shake it off and move on.

Be over the top. A friend wrote that “Last summer I had a guy gushing over the fact that I was the most beautiful woman he´d ever seen (!!!!!!) and couldn´t actually put a sentence together without having to stop and breathe. I still can´t work out if he was joking.” To do something like this, even if meant as a compliment is way too much. Telling someone they are beautiful is great. Doing it in a way in which they can’t tell if you are sincere or not, is um…not so great.

Be awkward. Coming from me this is rich. I can't really give tips as to how to avoid this, since it's something I am still learning. All I can say is to avoid it.

***Three tactics that have worked:
1. My friend Harry swears by getting someone to teach you something.  Obviously you have to be in conversation with this person for this to happen. So for instance, if the person you’re talking to mentions surfing or cooking, it’s the perfect opportunity to say, “I’ve always wanted to learn how to X!” if they’re into you, chances are they’ll offer to teach you. Only do this if you mean it though. If you can't swim, don't ask for surfing lessons. 

2. Another friend of mine accidentally picked up a guy when she went up to him and said, "Listen can we have a pretend conversation because there is this really creepy guy who is bothering me and I want him to go away." The guy she approached responded with, "How about we have a real conversation instead?" They got together shortly after that.

3. One night at Mao's, my friend and I spotted a very attractive guy at the bar. I have no idea what came over me, but I marched over to him and started speaking to him.  It went well. Sometimes the simplest approaches are the best. 

These aren't fool proof. The reality is that every situation is different, just with people being the variables there is no real way to control a situation or how it's going to go. The best way to look at it, I suppose, is that you've got nothing to lose and everything to gain. Starting a conversation is just that, a conversation...wherever it leads is another story. Maybe nowhere, maybe a friendship, maybe a romance. You'll never know until you try, and the worst that happens is that you'll have to try again. 

*thanks to "Blue Shirt" who was the original inspiration behind this post; and an even bigger thanks to all of my friends who so generously procrastinated from their day to respond to my email. You anecdotes and tips were wonderful. I promised that I wouldn't divulge my sources but you know who you are

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