Hey Katie! One of my coworkers is really attractive and I've always wanted to go up and chat with her but I can't seem to find the courage to do so. How should I approach this?Date Me, D.C. says:
You "can't seem to find the courage?" Reach down and between your legs and squeeze. I'm assuming you've just touched a pair of balls, so now you know they haven't skipped town in the middle of the night. PULL YOURSELF TOGETHER, MAN. I'd slap you silly if I could reach through the Internet.
You're clearly scared about rejection, and you shouldn't be. Why? Because WE ALL GET REJECTED. Without fail, every single one of us. You just need to take a breath, dig deep, sack up and start a conversation with this girl or else you'll always be wondering what if.
And even if she does ultimately reject you, consider this: Would you rather shit your pants, or die of constipation?
I rest my case. Now, onto how to actually do the approaching.
First I need a little more information. What kind of place do you work in? Do you have to interact with her in some work-related capacity? This is actually a disadvantage -- you've already established your role in her life as Guy I Have To Talk To For Work. Once your role is set, it's hard to change.
However, despite those odds, if you're hellbent on talking to her I'd wait until the stars align for the following opportunity: 1. You have actual business with her; and 2. She's not otherwise busy, i.e., she's taking a Facebook break when you arrive at her desk.
Then I'd start a casual conversation just like you'd do with any other co-worker. Ask her how her day is going. Look for a point you have in common through the objects on her desk. (On my desk, for example, I have a picture of me and Ingrid Michaelson from a concert I went to in 2012. If someone wanted to approach me, asking about the picture/concert would be a good place to start.)
If you do not directly work with her and have never spoken to her before, here's your line: "Hi, I'm [Name]. I see you here all the time; what department do you work in?"
And you're in. It really is that simple. Women are not as complicated as popular literature would have you believe. Ask a few more questions from there until you're chatting amicably. Remember also that much like the way you're supposed to act with wild animals, don't show fear (we can smell it, and it's unattractive).
Next -- and this is VERY IMPORTANT -- in BOTH cases, once you've had a casual conversation, the VERY BEST THING you can do for yourself is organize a happy hour with your co-workers and invite her along. You'll be able to get a better read on her in a situation that allows you both to relax and get away from having to maintain strict professionalism.
Trust me. Happy hour. Do it.
Now that I've said all of that, it comes with the following caveat:
STEP 1 IS ALWAYS DON'T. BE. CREEPY.
I really cannot emphasize this enough. And how can you know if you're being a creeper?
This is actually key in so many more facets of life than dating, but it particularly helps you out in this arena. The most basic is her smile -- when you're having your casual chats with her, is she smiling with her teeth shown? Did the muscles around the corners of her eyes flex too? That's a genuine smile (or a "Duchenne smile" if you're a nerd). On the other hand, is she smiling with pursed lips and wide open eyes? She's just tolerating your presence and wondering when she can get back to Facebook stalking her ex. Obviously, it's important to note the difference and stay or go accordingly.
That's just the tip of the iceberg, but it's the easiest one to spot. I wish I could say "you'll know if you're making her uncomfortable" but I've gone on too many dates with socially inept weirdos to state this as a guarantee. Just watch her body.* Posture, arm placement, etc. It will tell you what you need to know.
Also under the don't be creepy header: Are you within the acceptable age limits for dating her (she's no younger than half your age plus 7, so if you're 35 she's at least getting ready to celebrate her 25th birthday)? Do the math. You don't want to get a reputation as "that creepy old guy" at work.
And lastly, I'd be remiss if I didn't say don't jeopardize your job. A lot of work places have rules about fraternization. If she's your subordinate or, for that matter, your supervisor, I'd think twice about it. Also, if you date and things go bad, you will have to see her every godforsaken day, so keep that in mind, too.
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*With your peripherals, dude. Refer to Step 1.