• Things might be a bit too obvious and noticeable to others if there’s no reason for you to be interacting with him, so create excuses and situations where you need to see him for work-related reasons (like working overtime together – just the two of you). It doesn’t even have to involve actual work, e.g. a coworkers’ lunch or night out – this also has the advantage of being able to see what he’s like in casual environments. And of course if you want to it’s now easier to progress to a date (but avoid your work clothes when you do!).
• Ask him lots of questions and listen – then find opportunities to compliment him (“You did what? You’re such a warm person!”). Lots of humor and laughter are also important, but remember that it’s both about being funny yourself AND laughing at his jokes.
• While dress codes can be strict depending on the workplace, you should take advantage of anything and everything that you do have the freedom to style to the fullest (e.g. not allowed to wear heels? You can still wear stylish flats – or choose to focus on your earrings instead) as long as it isn’t inappropriate.
• Remember that there are legal, professional and personal risks associated with flirting at your workplace (anything physical is an especially big nono), e.g. you might get sued for harassment, you might be passed over for a promotion (or even get fired) or it might negatively affect your relationship with other coworkers.
• Don’t use company email to flirt – they are usually monitored by higher-ups. Handwritten notes and letters are a more discreet alternative – not to mention much more fun.
• Only flirt with one guy at a time to reduce the risk of problems.
• Forget about it if it’s a coworker who’s above you in the organizational hierarchy – they would be in a position to cause a lot of trouble for you if they don’t like your advances compared to an equal-level coworker or under.
• Remember that playing hard-to-get and being unpredictable is part of flirting.
• Be subtle – the workplace isn’t a club. It’s easy to get the message across with even slight deviations from standard professional behavior – something as simple as standing a bit too close for a bit too long, unnecessarily brushing hands when handing something over and even doing work-related favors for him (this also earns points by demonstrating competency, but it works in reverse too: asking him for help stimulates his “damsel in distress” instincts – who said flirting at the workplace can’t be productive?). In fact, if you’re careless it’s too easy to do this to someone you’re not interested in and send the wrong message – if anything most guys read too much into small things, so take advantage of that.