Can You Flirt at Work Under the Radar? Why Yes You Can | Girls Chase

Can You Flirt at Work Under the Radar? Why Yes You Can

flirt at workIn the post on indirect game, Dave asked the following about flirting at work and in other non-anonymous social situations where romance may not be the focus of the gathering at hand:

Hello Chase,
there's something about indirect rapport I'm not sure you've covered and it might be interesting. Very often and especially with girls whom you're likely to meet again - colleagues, fellow students etc. - it seems to me going true indirect could make sense (while still being sexy that is, but not saying "I'm kidding, I just thought you were cute" which is in fact direct but just delayed 3 seconds) because it allows the girl to pretend she didn't know you were seducing her. She can then tell herself (or her friends) that she's completely innocent and didn't help you or make it easy for you. On the other hand, directness and indirect direct polarize reactions so it can easily become awkward if you have to see them on a regular basis afterwards. Maybe you could add a few words on this.

It's a tight rope to walk - how do you express interest and flirt with colleagues and coworkers without being so obvious about it that you risk an ugly rejection or a (decidedly non-professional) label as the office flirt?

I'm going to focus mostly on work situations here, largely because we've already covered the classroom (see: "Cute Girls in Class? Stop Flirting and Start DATING"). As with that article, the topic here is going to be not just how you can flirt with (a modicum of) subtlety, but also how you can actually make something happen.

Because, while flirting is undeniably fun in its own right, taking that coworker you've been flirting with for months for a hot date or a roll in the hay is a lot more fun.

flirt at work

Unless you're just about to leave your job and don't care about your reputation anymore, or you only ever deal with people you're never going to see again and who have zero impact on your performance review - and if that's the case, why are you reading this and not just asking her out? - you probably don't want to be doing anything that risks jeopardizing your employment or career.

Sex is great and all, but as far as where it stacks up on Maslow's hierarchy of needs, I think you'd have to put it somewhere slightly less pressing than putting food on the table.

Money first, romance later.

So let's go over the ground rules - how to flirt in the office without turning your life upside down.

What Constitutes Flirting?

The ever reliable James Bond-Moneypenny flirting relationship there on the screen. That, to me, represents the classic modern work flirt dynamic (although that last scene, if you didn't see the movie, isn't really flirting; it's actually Moneypenny's virtual reality fantasy, which the real Bond then interrupts. You can skip watching that part, unless you're really into Moneypenny/Bond scenes, in which case, watch away).

Office flirting has changed dramatically over the years - if you watch the old Bond films, it's completely different.

In old Bond films, the woman (Moneypenny) flirts by constantly asking the man (Bond) to buy her a ring, or by virtually throwing herself at him... while he demurs. These days, as in the clip above, the man (Bond) tosses innuendo the woman's (Moneypenny's) way, and the woman resists, casting the man as a roll-your-eyes playboy who doesn't understand the way things work in the modern workplace... before "finally" giving in and flirting back herself, with a sort of "in your dreams" note to it.

You'll also notice that there's a large string of "If only," in Bond's flirting; it's a great example of the use of barriers. "If only that didn't have to be so," "If only we wouldn't end up court marshaled," "If only this or that."

The use of "If only," allows Bond to suggest things without suggesting them, because it's clearly a joke. Moneypenny is left without knowing if Bond really wishes "If only"... or if he's only joking.

Make a mental note of that - we'll come back to it again later.

The Office Flirting Ground Rules

flirt at workIf you're a street hustler, you have the Notorious B.I.G.'s Ten Crack Commandments to live by. "Keep your family and business completely separated" and "never get high on your own supply" are my favorites.

For those of us who aren't street hustlers though, and rather workplace flirts, we need a different set of rules. If you don't like big numbers though, not to worry; there are only six (6) of them here.

After graduating high school, I did everything I could to get hired by one of the "cool" clothing companies, and work day-in and day-out with model-esque girls. I figured that'd be a good way to get my game on point. But, I didn't have quite the right image then... and I got turned down by all of them. So next, I tried to get a job as a waiter somewhere with pretty girls working as servers... but I had no luck there, either.

I ended up working as a grease monkey in an auto shop instead. Not a lot of women there. And the ones who were there weren't exactly the kinds you'd want to date. In fact, I'm not even sure they dated men.

It wasn't until I graduated from university I finally found myself working somewhere, in mid-2006, with a reasonable amount of attractive women. As a business consultant for one of the best known and prestigious companies in the world, I found myself surrounded by women who were beautiful, intelligent, educated, and ambitious, with killer personalities to match. Exactly my types.

Except, I had no idea how to flirt at work.

One of my first days there, I decided to go invade the cubicle of one of the hottest girls working on my floor... but soon after I got there, a couple of the more experienced guys nearby, who also had their eyes on her, noticed someone was moving in on "their" woman and dropped in to defend their territory.

"Way to break out the sexy pose!" one of them commented my way, noting my... decidedly obvious way of leaning against the girl's cubicle wall, ultra-relaxed. My competitor then immediately switched into talking to the girl about "important" business stuff (that he probably chose conveniently to talk to her then), and I was left feeling way too obvious.

That leads us to our first two rules:

  1. Don't be too obvious. James Bond can deal with M making cracks at his expense for flirting in the office, but if you're just starting out (like I was), you probably can't just yet, and you'll end up an easy target for men who want to compete with you and women who want to brush you aside. Take everything you normally do to flirt, and dial it down a notch. If you normally lean in, very close and intimate, while flirting... don't lean in quite so close. If you normally toss about sly grins... make the grins you toss about a little less sly. Make people at least wonder whether you're really flirting or not - unless you have the experience and the savvy to shrug off those blows and flirt mercilessly regardless.

  2. Don't flirt in front of other people. Another piece of low-hanging fruit here; don't let other people spoil the party between you and that cute girl in HR because you started flirting out in the open. People will step in and rain on your parade for any number of reasons; some of them are the competition, and want to derail you from landing that sexy colleague before they can; others are just bitter and dislike flirting and flirters in general. On top of this, there's social pressure to worry about, too - while she might be flirty in private, there's a good chance she clams up when there's an audience nearby, even if it's only an audience of one. One is all it takes to tell the whole rest of the workplace...

As I got my legs under me in my new job and my new place for clandestine flirtation, I soon found another very pretty girl at work who seemed like the ideal candidate for a little workplace romance. She was fun, cute, and seemed to genuinely enjoy my sense of humor... and me, for that matter.

So, she and I went for lunch, and I turned on the charm hard. She bit. I was a smooth operator and she loved every minute of it. I was killing it. And then...

I didn't do anything. I'd get her another day after that.

Wouldn't you know it, she got weird. Of course... attraction has an expiration date. But I hardly knew that then - I was just starting to piece that sort of thing together.

I know better these days though, and that brings us to our next two office don'ts:

  1. Don't go too deep in the office. Slow down, Casanova... it's not a date. It's work. And unless you've got a private corner office you can sweep her off into without anybody noticing, and neither of you have any commitments for the rest of the day, you don't want to go getting a colleague to the point where she's ready for something to happen right now. Because that leads to a LOT of disappointment and loss of interest in you if it doesn't... when you bring someone close but don't take them over, it causes resentment and spite. And you can't take them over at work. The only exception: the two of you are working totally alone after hours, or some other one-on-one, interruption-free scenario. In that case, go as deep as you please - but do make sure to please. Otherwise, it won't be any different from the usual "wrong place, wrong time" scenario.

  2. Don't do anything else to bring a colleague close to "peaking" too soon. Right along with going too deep in conversation comes anything else that can get your coworker to the point she's ready to jump your bones right now in the office... if only all these people would just go home. Just like going too deep, making her peak too soon - with too much sexual innuendo, too much chase framing, and the like - then fail to deliver, and you'll end up with a very disappointed (and mildly disgusted) officemate on your hands.

After I moved out to California, we had a new teammate join our team. She was spunky, pretty, and lots of fun - and I figured I'd line her up for the kill.

Unbeknownst to me though, the quiet, nerdy guy who'd been showing her around the office and getting her acquainted with our project beat me to the punch - and one night not long after she'd arrived, when the three of us were at a nightclub after hours, I walked back from grabbing drinks to find the two of them making out like junior high schoolers. Kudos to him!, I thought; they left together soon after, and I found myself rather grateful I hadn't pursued the girl too aggressively before knowing the lay of the land, and made a fool out of myself. I downed my drink that night and set to work running a little solo club pickup; can't win 'em all, you know.

That leads us to our final two rules of flirting at work:

  1. Don't start driving before you know the terrain. It's impossible to ever completely know what's going on - that coworker of mine who got together with the quiet nerdy guy end up dating him for 4 or 5 months, until she broke up with him for being a little too needy. Not long after, she went home with another colleague of ours - only, much to his dismay and her hilarity, he could not perform. I heard all of this because she and I became friends - I doubt either of these men knew about their fellow officemate a few cubicles over. Even still, get a feel for what a girl's ties are to men in the rest of the office - many of the people who flirt, date, and sleep around at work do it a fair amount, and you never know when you might be stepping on another colleague's toes - or your boss's.

  2. Don't tell other people or announce your intentions. Goes without saying, you'd think, but I've seen some of this machismo or one-up-manship where a guy announces he's going to bed a certain new girl, and things along that line. There're all kinds of ways this can go wrong though - your colleague may get wind of this, and very well change her mind about you; you can end up looking rather weak if you "call it," and someone else who didn't say a word beats you to the punch instead. Keep your intentions to yourself - no one else should know what they are... or even suspect what they are.

There. If you respect those six rules when you flirt at work, you'll be covered - and we all know the workplace of today is all about C-Y-A (sadly).

Again, our six rules for office flirtation are:

  1. Don't be too obvious
  2. Don't flirt in front of other people
  3. Don't go too deep in the office
  4. Don't do anything else to bring a colleague close to "peaking" too soon
  5. Don't start driving before you know the terrain
  6. Don't tell other people or announce your intentions

Mind those, and you'll be as clean as an office flirt can be (which, isn't actually pristine, but is still at relatively harmless levels).

And now that the CYA is covered, let's talk about the how to.

flirt at work

It took me a while - partly because I ended up working mostly with people just about to become retirees (the average age for the people working in the branch of the U.S. DoD I was working in was 55.8 or something crazy like that - I saw an internally-circulated chart on it, called something akin to "The Impending Staffing Crisis" - impending meaning everybody's about to retire, so then what?), but before leaving the workforce I did finally figure out how to not only flirt with sexy colleagues, but actually turn that flirtation into something substantial, too.

Flirting can be a little sticky when you have a bunch of rules regulating it - one of the reasons I vastly prefer cold approach to social circle (work being a social circle environment itself) - but if you've done a good job making yourself attractive to the opposite sex (see: How to Be a Sexy Man) and you've got a solid, sexual vibe going, you've already got the necessary components for having relatively easy success in the workplace.

And if you haven't got those things yet, well... you've still got a shot. But you ought to be working on having them as a top priority! There's no shortcut to office or any kind of romance quite like already having worked to turn yourself into a head turner and eye-popper. Fundamentals are #1 all day long, regardless who you are.

Without further ado, here's our how-to.

How to Flirt at Work

flirt at workIf I learned anything about male-female dynamics from the working world, it's that flirting can bring both a lot of fun and a lot of frustration into your daily grind. There's another side to it, too - the long period of time most office flirtations unfold over really heighten the emotions involved.

That means you can easily run over a colleague's heart if you handle it with butterfingers... or, if you aren't too careful, she might do the same to you.

I've never gotten so hung up on an officemate that it messed with my head, but I've had the reverse happen - women from the workplace that I took to bed, but who ended up going a little too crazy for me. All that proximity, buildup, and anticipation does funny things to the mind... including making colleagues who hardly know each other in real life fall in love with each other in the office purely out of fantasy and flirtation.

So do be careful about this - have fun with it, but don't be a heartbreaker.

  1. Break out your sexual vibe. The sexy vibe is your #1 office environment tool for flirting at work without getting "caught." If you exude sexuality, you can make anything you say flirtation. When I coach guys on this in person, I usually have to demonstrate - they tell me things like, "Well, I've been trying to include sex talk and sexual innuendo when I'm talking to girls a lot, but it just doesn't feel like it's working!" My response is always no, no, no - talking about sex is not sexy. Being sexy is a way of communicating - when you're doing it right, everything you say sounds sexy. You can walk up to a colleague and ask, "Reports done yet?" and have it absolutely drip with sensual undertones. Quick tip: if you're still a beginner on being sexy, get accustomed to talking the same way you do in the bedroom. Instant sexiness.

  2. Use chase framing. When you use normal sexual innuendo, you can too easily offend, show all your cards, be too obvious, or look like you're chasing. Instead of this, you can use chase frames, a form of sexual humor in which you imply your coworker is chasing you... rather than the other way around. Like so:

    Her: Reports done yet?

    You: [in a sexy tone of voice] Always after me for my reports, aren't you, Susie?

    Her: [sexy voice, playing along back] Well you know I'd be lost without them, Rick.

    You: [still a sexy voice] I'm sure you'd figure out something. There's always Peter [pick some guy she'd never date in a million years] over in marketing.

    Her: [still flirting] Your reports are the only ones for me.

    A side benefit of chase framing is it's easy to call off if the other party doesn't bite. So, if you tell her she's always after your reports and she gives you a boring office response back (instead of flirting), it's a snap to switch back into normal office mode without having sounded overly flirty.

  3. Flirt in bursts. Just like in a bar or a nightclub, a coworker when she's meeting you for the first time in an office setting is usually wondering if you're going to be a social burden or not - if you're going to be one of those people who says "hi," and then just stays and stays and stays and never leaves until she has to tell you it's time for her to get back to work. So - especially if you're dropping by her workstation, or you're catching her in the hall somewhere - make sure your flirting is coming in short bursts. Like this:

    You: [noticing your colleague in the hall] Cat, how'd the weekend go?

    Her: [she stops to talk to you] So-so. My friend had a birthday on Friday so we all went out for that.

    You: [in a mischievous tone] I can't believe I wasn't invited.

    Her: [not sure how to take that] I didn't know you wanted to go.

    You: [sexy voice] I'm kidding. The only one I'd have known there would be you... we'd have been stuck together all night, and what fun would that be?

    Her: [mock hurt feelings] You don't think it'd be fun being stuck with me all night?

    You: [sexy voice] Well, depends what we're doing. Anyway, I've got to go see the boss - more account reconciliation stuff.

    Her: [flirty] Sounds exciting.

    You: Always is. [walk off]

  4. Use barriers. Just like James Bond, you can make good use of barriers to build intrigue, up attraction, and tempt your coworker(s) to pursue (I talked about barriers before in the article on being a challenge if you want a bit more on these). Bond uses plenty of "if only" to add an element of mock-longing to his barriers; he's pretending to seem like a hopeless romantic, which pokes fun at the hopeless romantic archetype and paints him as ever the roguish bad boy in contrast. An example of how these work:

    Her: Reports done yet?

    You: [in a sexy tone of voice] If only you wanted me for more than my reports, Susie.

    Her: [sexy voice, playing along back] You know I'd be lost without them, Rick.

    You: [still a sexy voice] Someday we really should run away from this place, and leave all the reports behind.

    Her: [still flirting] If only we could... but then who would deliver the reports to Mr. Richardson?

    You: [still flirting] You're absolutely right, Susie. Thank God one of us has a good head on his shoulders.

    In addition to being a mischievous way of flirting and a way that paints you as a bad boy mocking the romantic nice guy, barriers also give you the advantage of serving as a form of role-playing, and a means of planting seeds of an idea in your coworker's mind. Even though it's merely fun and games, she still gets the idea floating about, potentially to be imagined later - as a fun sort of daydream (running away with you and throwing away the reports).

  5. Never "end" your flirting. When walking away from a flirty conversation, do not

    • Say you'll see your colleague later anywhere (sounds like you're planning... not sexy; also puts her on the spot and forces her to mentally run through her schedule - not good)

    • Try to close / set up a date / grab a phone number (looks like you'd been meaning to, then jumped on an impromptu opportunity... again, premeditated, not natural)

    • Say "goodbye" - this is light, informal flirting, it doesn't really end with any kind of formality or finality

    If you stay away from any kind of "ending" other than "Gotta go do X - always a good time..." (said in a sexy voice with sexy eye contact, of course) and take off, you'll be fine.

On touch: touch is one that I recommend you play by ear, as it's highly dependent on the work environment. I've known men who were heavy touchers with their workplace flirting, because it worked in those environments - places like bars, restaurants, modeling agencies, etc. Those are places where, if you're sexy, it's very easy to end up with coworkers sitting in your lap, coworkers whose behinds you're slapping, coworkers who are walking up to you and hugging you or kissing you on the cheek, and the like.

Contrast that with an office environment, where even nudging a colleague likely comes off as strange and uncalled for, and you'll want to avoid it at all costs, even with colleagues you're on very friendly terms with (usually).

If you're not sure where on the spectrum your office environment falls, take your cues from the other people there - especially the women. The women are the most attuned to the social environment - if they're being touchy, it'll be okay if you are too... provided you do it in a smooth, sexy, attractive way, that is.

How to Do MORE Than Flirt at Work

flirt at workI promised you this article wouldn't just be a "how to flirt at work" article, but rather a "how to flirt at work and get RESULTS"-type piece as well.

So here it is.

  1. Keep coworkers you like on the periphery. It might seem like counterintuitive advice, but just like hooking up with friends, getting together with colleagues is all about not letting things get stale or comfortable or "fixed" before you're ready to strike. That means, don't get close to her until you're ready to ask her out somewhere. If you get close to a colleague before you're ready to make a move, you stand a very good chance of both you and your colleague getting into a "rut" of "just" flirting... which perhaps some part of each of you would like to evolve into something more, but it becomes increasingly difficult to pull off as more time goes by and you both get more comfortable merely flirting and no more.

  2. Date outside your close circle. Again like with friends, not only is dating people close to you often difficult to do - unless they're very open-minded - but it's also impractical for "what happens after" reasons; that is to say, someone always gets feelings. It might be them, if you've got your game on lock; or, it might be you, if you're not exactly swimming in abundance with the opposite sex just yet. Either way, if there are messy close feelings going around with someone you see every day, those are very often one-sided, and very often not good for work. I've known a fair number of people who had to change jobs because of failed relationships / flings with close coworkers - maybe think of dating someone from your close circle as another form of incest. Leads to nothing but trouble...

  3. Follow the standard guidelines for getting contact details. That is to say, when you go to get a phone number, make absolutely sure you've proposed a meet up for food or drinks sometime first. That way, you a) have an easy, practical reason for wanting contact information in the first place, and you b) don't need to spend time trying to figure out how to convince your colleague to come out with you now that you have her number. All you have to do is text her to figure out logistics, and you're set.

  4. Roll your date request in with some form of scarcity. When you've known a colleague for a while, it can seem odd to suddenly ask for a date out of the blue - you need some kind of reason, and simply waiting for the high point of the conversation (which you should do anyway) isn't enough. The most effective way to get dates with colleagues you've known a while is when you couple the ask with a "going away" message... like:

    You: [noticing your colleague in the hall] Hey Bree, haven't seen you in a while!

    Her: [she stops to talk to you] Hey Harry! Yeah, you just disappeared all of a sudden.

    You: They've got me trapped in the dungeon doing all kinds of crazy mad scientist work on metrics and PowerPoint presentations. It's good stuff and I'm getting to work with a lot of the higher-ups, but it's pretty grueling work, too.

    Her: Well, that sounds like good work to have!

    You: Yeah, it's not bad. What've they got you doing now - same stuff?

    Her: Same-same, yeah. Nothing all that exciting.

    You: Right on. I probably won't see you much around the office since I'm on lockdown 24/7, but let's grab a bite sometime this week or next, you and me.

    Her: Cool, I'm down.

    You: Rockin'. Let me grab your cell and I'll text you for details, assuming they don't take away all my possessions when they lock me back away down there.

    You typically want to make it sound that the reason you've been scarce is because you're on the upswing, not the down. Whenever there's change in the office, you're either a) moving up, b) moving down, or c) moving laterally. The first one is good, the second is bad, and the third one sounds like nobody wants you. Go for #1.

  5. Plan a date where she isn't likely to bring more colleagues. Lunches with big groups of coworkers are fun - unless they're supposed to be one-on-one lunches with a romantic prospect, that had a bunch of other people either jump in uninvited (and if other people hear you're planning a lunch / happy hour / dinner, it's not too uncommon for them to invite themselves along like this - I've had it happen, and it's not fun for you or her), or your colleague invites them along herself to be nice / friendly / sociable, or because she isn't sure of your intentions and figures "whatever" (or because she IS sure of your intentions, and isn't sure she wants things to get too serious). Some good non-group activities include:

    • A late or early lunch - pick a time when no one else is likely to be available, and where she'll need to do some scheduling around to make sure she's free - a coworker's also a lot less likely to invite people if the lunch is planned at a weird time (e.g., 10:45 AM, or 2:15 PM in the afternoon)

    • An off-day, impromptu happy hour - if you want to take a colleague for drinks after work, make it an impromptu message toward the middle (not end) of an "off day" - a day when people at your office don't normally go out for happy hours. If you make it mid-day, she won't have much time to invite other people - or for others to hear about it and invite themselves along

    • A party invite - while my general recommendation is that you should stay clear away from party dates, when it comes to a setting like the workplace where a coworker sees you one way, interacting with you in a party environment can help push her to see you another way, too

    • A "stay after work" date - this is the one where there's already a good deal of sexual tension between you and a girl, and it's "excited" tension (where you can tell she wants something to happen), rather than "nervous" tension (where it seems like she isn't sure how she wants to play things out). If you can find an excuse for her to stay after work with you - perhaps, say, to work on something the two of you are working on together, or that you need her help on - and you'll be the only ones there, you can use this situation to unleash the sparks that have been trying to fly

Once you have a coworker out on a date, you run it the same as you would any normal kind of date, as well. One note - fast sex is more common among colleagues than almost any other demographic I've seen. I've seen it with restaurant staff and I've seen it with business consultants. I've seen it with teachers. I've seen it with office workers. Tension builds and builds and builds... and then the instant you get two people alone together - with or without throwing alcohol into the mix - something explosive is the result.

If you're planning on a "take it slow" traditional dating style of going about courting a colleague, you'll almost certainly be in for disappointment - and so will she. It'll flame out, and you'll go back to (awkwardly) working together.

Instead, go for fast - move fast and pursue first-date sex.

It is, generally speaking, the way things go down outside the office.

Work Flirting Wrap Up

To put a bow on things -

The Office Flirting Ground Rules:

  1. Don't be too obvious
  2. Don't flirt in front of other people
  3. Don't go too deep in the office
  4. Don't do anything else to bring a colleague close to "peaking" too soon
  5. Don't start driving before you know the terrain
  6. Don't tell other people or announce your intentions

How to Flirt at Work:

  1. Break out your sexual vibe
  2. Use chase framing
  3. Flirt in bursts
  4. Use barriers
  5. Never "end" your flirting

How to Do MORE Than Flirt at Work:

  1. Keep coworkers you like on the periphery
  2. Date outside your close circle
  3. Follow the standard guidelines for getting contact details
  4. Roll your date request in with some form of scarcity
  5. Plan a date where she isn't likely to bring more colleagues

... and, as always, move faster. Make things happen faster. Don't dawdle.

And remember: flirting in the office is fun. Getting together with coworkers is even more fun. But, don't burn down your employment or drag some smitten coworker's heart through the drainpipes for the sake of it - use a little tact, and a little awareness, before you go nuts flirting and dating at work.

That said, assuming you're tactful and aware enough, it certainly is an enjoyable thing to go nuts flirting and dating at work.

Chase Amante

Chase AmanteAbout the Author: Chase Amante

Chase woke up one day in 2004 tired of being alone. So, he set to work and read every book he could find, studied every teacher he could meet, and talked to every girl he could talk to to figure out dating. After four years, scads of lays, and many great girlfriends (plus plenty of failures along the way), he launched this website. He will teach you everything he knows about girls in one single program in his One Date System.



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