How To Approach A Guy You Like And Keeping Your Cool

Omigod, like, he’s like really cute. Like really, really cute, like. Did I forget to mention cute? We get it. That guy at the gym who deadlifts the pounds like a breeze, that guy you connected with on Facebook who seems way out of your league, or that insanely attractive man at work who should have been a model. Cupid’s bow can come darting at you from all different directions. At this point you’re like, whoever said all the good men… wait, which planet are they from? Here you are, smitten by a guy so hard you’re kind of already trying to decide between ivory and pure white for the wedding dress (You’re not? Am I the only one who does that? Damn gurl!) Or maybe it’s not even about how the guy looks. Maybe he’s this genius wizard type at work and has unknowingly done you a huge favor at some point, and you really, really like him for being so smart and kind at the same time. Or maybe beyond those rippling muscles on the guy at the gym, he has a creative soul and is actually a painter by profession, and this lethal combination of a strong body and a soft soul has swept you off of your feet. Or that guy who met online has simply been very respectful in his conversations (reference: some very, very nasty guys we encounter online every day) and you’ve started growing fond of him for this simple reason. And even if it apparently seems like nothing, it is important to you, because that’s the power of unexpected good behavior these days! But the bottom line is, you really like this guy.

Here’s where you hit yourself on the head for thinking and worrying too much about this. First, he might be, at the moment, the most exotic thing you’ve ever set your eyes on, but he’s still just a guy. A normal human being. It’s understandable, the crazy feelings you’re experiencing right now and your nervousness around those feelings, but you need to get a grip on them if you ever want to make it to the next level with this awesome guy. And for that, you have to turn down the awesome in your head a little. There are two reasons for this. One, it just might be a figment of your imagination born out of your feelings for this guy, and if you were to later find out that he’s not all that awesome after all, you’d be disappointed and not take the association any further. Even though he might be a perfectly alright person otherwise. Sometimes our projected ideas about a person (from staring at and appreciating him from afar for far too long) are too demanding of that person and it eventually all ends in disappointment. The second reason is more important. And urgent! If you don’t stop worshipping this demi-god, you will never ever gather the courage to approach him. And even if you do manage to talk to him, you’ll never be able to keep your cool for long enough to make any conversation that makes sense. Which will basically send any chances you had with the guy down the drain. Don’t be that girl who never goes on her adventures to find out what happens next!

Once you’re internally convinced that the guy is made of human flesh just like any of us and didn’t just walk out of a Michelangelo painting, it is time to devise a plan to nail... the art of approaching him (what were YOU thinking?) without hiccups. And have no doubts, we’re talking full on stealth mode here. It is a battle, and one that you must win. I know what it sounds like, and I promise you, you aren’t unintentionally caught in the middle of teen romance drama movie script, but it IS romance, and in every romance, there IS some kind of drama. Can’t possibly deny that? And the drama in your life is that you’re too shy to approach this guy. At work, in the gym and on Facebook –you see him almost every day, you’re so familiar with him and you’ve also started feeling you have a connection with him, but you just don’t know how to take that first step ahead. You’re afraid you’re going to lose your cool and completely freak out when you approach him for the first time. But here’s the thing: everything in this world starts with a first time. And know this for a fact, even if you made a complete mess of yourself when you approach him, you’ll never know how you would do if you never approached him in the first place! However, the goal of this post is to make sure that you DON’T have to make a mess of yourself at all. And that is achieved by planning. It’s not as bad as it sounds, and you don’t need inspirations from Mean Girls, it’s simply to be self-aware and knowing which action leads to which consequence (getting the guy to talk to you, or getting his phone number, asking him out, making him ask you out — whatever’s your goal).

The first step to this plan is to know and understand the guy. You can’t possibly devise a plan to be cool and confident in front of him without having the slightest idea what kind of a person he is or what he likes and dislikes. That is why you should take some time ahead to observe your “subject”. Don’t rush this process. The key to be confident in your skin and not shaking at the knees when you approach this guy is to be armed with the right information. Not that you’re going to manipulate him or something, but it is just helpful to know that he’s as much human as you and has just as normal likes and dislikes like you do. Because at the state of mind you generally are in when you like a guy, he seems all but perfection. But as you to get know him, you’ll see that he’s not all that intimidating after all. And then it won’t be so difficult to approach him, whether online or in person, at the gym or at work. And for that, you need to take the time to observe him from a distance. Now I know you’ll say that’s exactly what you’ve been doing all this while, but all that time you were only really just gawking at him, not looking to get to understand him. Your observation now has to be more targeted and with specific intentions. You’re working on turning the tables here.

Basically, get into his head. Learn whether he likes cats or dogs. Learn whether he likes his steak rare or well done, whether he’s a beer and nachos guy or a spaghetti and wine guy, and about his favorite pizza place and how many times a week he visits. Learn about his favorite movies and TV shows, and the book he’s currently reading. Learn — and this one’s important — WHY he broke up with his last girlfriend (through the grapevine of course, you’re still too “shy” to approach to him). And what kind of girls he usually likes. Don’t stalk him of course. We're NOT promoting that kind of behavior! Give him the respectable distance any person should have, and be discreet about the whole observing thing, don’t just go snooping around everything he owns. But if you are sensitive to his behavior and the way he talks to others, you’ll pretty much get to know a lot about his likes and dislikes and his overall “type.” The reason you’re doing this is not because you are that crazy stalker we read in the crime section of the newspaper about, and definitely not because you want to do everything in life exactly like he likes, but because you want to know the guy in order to work your confidence before you can approach him. And like we all know, knowledge enhances confidence. Without knowing anything about him, you’ll KNOW you’re taking a blind shot which will likely demotivate you from approaching him at all. Which is a great loss for you, and a great loss for him (‘cuz you’re awesome, duh!).

This is kind of obvious. Being in close proximity will help you both with the “research” and for multiplying the chances of getting to approach him (someday, someday). Make sure you’re around him, you know, “just casually hanging out, you weren’t even aware he was there”, for as much time as you can manage, and which doesn’t hamper your work or your meals (although, if you REALLY like the guy, that might already be happening). So if you meet this guy only during that time when you’re leaving the gym and he’s starting, book yourself a slot with him. Bribe your colleague into letting go of the cubicle or chamber next to his at work. And post a lot of pictures of Facebook, of yourself, of the potted plant at your apartment or your leftover meals from last night (don’t actually do the last two, I was only kidding) — whatever makes him take notice of you, potentially increasing the chances of him striking a conversation so you don’t have to approach him first. But also to feel great about the fact that HE approached you first!

Your most potent arms at combat — his friends! That's if, and only if, you can manage it and are close enough in his circle to get access to this guy's friends (or you’ll really be the crazy stalker we read about in the crime section of the newspaper). And “friends” doesn’t really have to mean his bosom buddies from his kindergarten days. They can be anyone who is slightly or majorly friendly to the guy than you are. And talks to them often. If you look around, you might easily find such people. Like maybe there is a guy at the gym he talks to every day about his progresses and they seem to bond over their common interest pretty well. Or that guy at the office he always takes a smoking break with. Or the guy he always seeks for help when it comes to work. If your crush is someone you met online, it’s easier to track his friends. Look at his friend list on Facebook. Or just “observe” the one or two guys who always like and comment on his pictures. Casually befriend them on Facebook too. Talk to them often and then, one day, “accidentally” spill your deep liking for this guy. Taking his friends or colleagues or gym partner into confidence helps in two ways. One, you get to know way more about him than you ever could by just observing, and two, they are potential matchmakers you don’t want to underestimate.

You won’t be confident enough to approach the guy if you aren’t secure in the knowledge that you have a very solid, plausible reason to talk to him. And you won’t be able to keep your cool (that’s the whole point of this post if you’ve read the title!) if you didn’t know exactly what you’re going to talk about for at least the next 15 minutes. We’re trying to avoid any awkward silences here. If you have a good reason to talk with the guy, you’ll also make him feel comfortable for being approached, because you never know for sure, he might be just as shy as you are. Finding a reason, though, is not that difficult. If you’re at work, there are plenty of work-related reasons you could cook up. At the gym, ask for additional fitness tips since you find him so effortless at what he does. Online conversations are even easier. Comment on any post or picture on Facebook and see a thread of discussions ensue. Facebook also lists his likes and preferences, so if he doesn’t post anything worth discussing over, just shoot him a private message with a question on one of those topics. Easy peasy! And if none of the above is quite comfortable a technique for you, remember that you’re friends with his friends. Ask them for suggestions, or better still, ask them to set you up. Like maybe all of you can plan to have dinner together, so you have a good ambiance to approach the guy. Eventually, they could also find an excuse to leave you alone with your guy. Beware, though; you have to roll your eyes an awful lot for this.

If you’ve done all the prep work thus far, you already have quite a lot of information on the guy to help you feel like you know him to be able to talk to him. Therefore, approaching him should come easy. Except for one little thing: Your confidence. Not just with respect to this particular guy, but otherwise too. How confident of a person are you? Do you have self-esteem issues regarding how you look or how to talk? It is easy to assume that you can’t approach this guy because you are shy from the fact that you like him so much, but are you sure the reasons aren’t deep rooted? Being shy on account of one guy is all right, but if you’ve always had the problem of not being able to approach people and initiate conversations with them, you have a grave problem at hand that needs to be addressed before you even attempt at approaching this guy. You need to be a more self-assured person to be able to hold your own and keep your cool when talking to a guy. Because we don’t realize it, but lack of confidence is very visible when you’re interacting with others. You tend to either talk way too much nonsense or that dreaded awkward silence ensues. Also, if you’re already suffering from low self-esteem issues, you will be further discouraged from talking to anyone if your conversation with this guy doesn’t go as expected. It’s a little easier to fake confidence online, yes, but if you really like the guy, you’d probably want to take things beyond the online conversations and then it would be a rude awakening. Being comfortable in your own skin, irrespective of what size or color you are, and how perfect your skin or hair is, or whether or not YOU think you look good, is the key to charming others during a conversation. Work on creating this paradigm shift that you are the best you’ve got and there’s no one quite like you. Therefore, you’re enough and more.

One of the prerequisites, if not a necessity, is feeling confident about yourself. The day you decide to finally approach the guy, make sure you’re looking as best as you know you can. It’s not vanity, or superficial mentality. Dressing up is a sign of respect for yourself as well as for the other person. Because they are the ones who will have to look at you, make sure you don’t look hideous! It’s not, technically, to “impress” him, but to present yourself in a way that you know he won’t disapprove of (that’s the data you collected from observing him, remember?) So if he’s the type that doesn’t quite approve of a full-face contour/highlight pancake makeup, you’ll definitely remember to keep the foundation light and add just a touch of mascara and blush. But above everything, it is for you that you’re taking care to dress up when trying to approach the guy. You want to look good because you want to FEEL good. Talking to someone is never a good idea if you’re constantly worrying at the back of your head about how he is this gorgeous being and you’re a peasant type and how are you ever going to impress him with your below average intelligence. No! You need to feel that you are unique in your own goodness and you work really hard at the gym too, so that sheath dress you’ve picked does a great job at flaunting your best assets. Looking at mirror and thinking “Wow I look great today” goes a long way in building self-esteem and confidence to talk to others. Of course, dressing up isn’t necessary when talking online, but you’d still want to follow through on this when you talk and meet off of Facebook.

You’re now finally ready to approach the guy, armed with all the knowledge and self-confidence one could need. The fact that you can just swing by and open with a line that you know will pique his interest (because you did your research on his interests) and the fact that his friends are well within reach if you get stuck anywhere, should be reason enough to stop being shy about it. Technically, feeling shy or lacking in confidence comes from the place of being unsure of how things are going to unfold once you approach him. But when you’ve already planned for it and have executed the plan to near perfection, you’re more in control of how things are going to pan out. And the short answer to that is things will go exactly how YOU want them to go. Not just because you make a great detective and have all that information about him at the tip of your fingers, but because you are also now secure in yourself and don’t have self-esteem issues regarding what you look like or how you talk. Once you own yourself and look at the whole thing as an event that will either get you a hot date or will teach you a lesson for life (one of them being never to listen to me perhaps), you get over your shy mode in no time. You’re a woman of today and the hero of your own doing, what’s stopping you from starting a pansy conversation with a guy? (Okay yes, that last line was cheesy AF I admit).

Remember, this lesson is not just for the sake of one guy (although, for the sake of YOU, I do hope you find the right guy in him), but for you to approach any guy any time and carry on a conversation with them without freaking out. One does get worked up and hysterical even when they develop a liking for someone, since you want to make sure that everything you do should only impress that person and nothing less would do. But this overexcitement and overenthusiasm over this one person make them seem so intimidating that your list of to-dos for impressing the guy keeps getting longer. And then the added fear of “What if he doesn’t like me when I finally go talk to him?” takes over and that time to approach him never arrives. Consider this a handbook for every time you feel that way about someone. The first step is to ensure that you don’t over-idolize the person you like or you’ll never make it past that stage. Next try and understand the guy better so it’s easier to talk to him. And finally, work on your own confidence, and dress up some to boost it, and then approach him. Talking to him will seem like the easiest thing you’ve ever done!