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Dear Geek's Girl, I work in a fairly large office doing IT work. I make a point of always helping a specific customer. She is WAY out of my league but we always have really great conversation when we talk and I always leave her desk with a smile. How do I bridge the gap between our professional relationship and ask her out?
-5wanting10
Asking out a coworker (or more generally, someone with whom you have professional dealings) is always a controversial topic with universal implications for geeks and non-geeks alike.
Before I step up to my soapbox o' love to beat you over the head with dating advice, I'll caution you to first consider the consequences of dating a coworker. How is your office? A harmonious bunch of team players? A bitchy bunch of busybodies with entitlement complexes? I suspect your office is somewhere in the middle of that spectrum, and if you do end up dating this girl, it will most certainly affect your office environment, for better or for worse. Do not proceed unless you've assessed the situation and found it accommodating to your comfort level.
Okay, now on to beating you over the head. You need to ask yourself a question. Why is it that you think she's "way out of your league?" Because she's pretty? Popular? Dresses well? What puts you in different leagues? You're not popular? You have a cowlick? You killed a guy?
Once you come up with an answer to the question, put it out of your head. It's crap, whatever it is. You cannot make any sort of judgment about your compatibility with this girl until you've actually given it the old college try. Maybe she's not really a 10? Maybe you're the 10 and she's the 5!
Next time you find yourself chatting with her, once you've taken care of your work obligations, just ask her out! Global Rule #1 of dating is putting yourself out there. If you're in violation of Global Rule 1, Megatron will punch you in the face. And your chances of landing a solid relationship will be significantly lower.
Ask her to lunch, or to mid-day coffee, or to a happy hour at a nearby pub. Lay your cards on the Formica. Be yourself. If she's the right gal for you, she won't balk. And if she does, it might sting, but at least you'll have the satisfaction of knowing you tried. Would you rather regret something you did or something you didn't do? Sure you might regret that drunken decision to get that unfortunate tattoo of a naked Green Goblin, but wouldn't you regret even more not knowing if you'd let "the One" get away because you never tried to ask her out?
Even if it ends in an uncomfortable situation, known that there are many fish in this great big sea. Trite but true. Just watch out for the Sharktopus.
