Sunday, November 15, 2009

Taking a deuce in your own nest

Dear Chuck

I’ve just realised I quite fancy a guy I work with, it’s been a bit of a slow build. Nothing has happened yet but I do think that there’s chemistry although I’m not sure how interested he is. He isn’t my boss or anything like that but we work in the same department so I am worried about making a move and him not being interested.

What should I do?


Tanya, Tanya, Tanya. You’re playing a dangerous game when you start contemplating fishing off the company pier. In this day and age when finding a decent bloke is becoming increasingly hard, Chuck can appreciate that women are expanding their search and considering options that were once taboo. Obviously, you spend upwards of 40 hours per week at work and are exposed to people that you see more often than friends and family so it is natural that you would get close to a decent-looking dude you work with.  

There are a number of issues at play here Tanya. First and foremost, Chuck needs to weigh up the pro’s and con’s of an office romance for you.


  • The obvious downside to engaging in an office romance is the threat of break up. If things go pear shaped, you will be constantly reminded of the way things were because you’ll see this dude every day. If things are particularly messy, the reality is that one of you may actually have to leave.

  • If you’re in the same team meeting as your boyfriend you will be viewed strangely if you agree with anything he says (“she’s only agreeing because they’re dating”) or if you disagree (“they must be fighting”).

  • Imagine if one of you gets promoted over the other and becomes the boss? Granted, you may enjoy having a master - servant relationship, in which case this may add some spice to things. But in reality one being promoted over the other could be particularly awkward, especially if you have to issue a particularly shitty job to him or vice versa.

  • If you try to keep things on the down low, the stress of sneaking around can add unwanted pressure to a fledgling relationship. Conversely, if you let all and sundry know that you’re an item it can bring unwanted attention and assumptions.

  • You will spend all your time with this guy. You’ll see him 40 hours per week at work and then after hours. Imagine dinner conversations:

“Honey, how was work?”

“Well you were there, you should know…moron”

  • When your boyfriend tells pussy stories at work – he’s talking about you!


  • You can car pool and save money
  • If you’re struggling with a piece of work, you can always borrow his.
  • You don’t need to sneak him past security so that you can hump on the boss’s desk.

  • You’ll always get your way in meetings with another person that has to back you up…or else you’ll withhold sex.
  • You’ll have someone to shag at the office Christmas function.
  • He cant use the excuse “I need to work late” if he’s having an affair.
  • You’ve always got someone to nail on work trips - no more trawling the hotel bar looking for beef.

As you can probably tell, Chuck can’t see a huge amount of upside in hooking up with a co-worker, there’s just too much that can go wrong. However, since we’re dealing with a matter of the heart and rational thinking tends to go out the window when your loins start to tingle, you’re probably going to press ahead and pursue this anyway, so it’s important to try to make an approach that allows you to see if he’s into you and covers your arse if he isn’t.

The easy angle is to go out on work drinks, both get intoxicated, bail him up in the corner of a bar and snog him. If he reciprocates, then you’ll have a fairly strong indication that he is interested (or horny). If he kisses you back but then later in the ensuing week suggests that he isn’t interested, you can pass it off as a drunken mistake. The downside to the drunken approach is that your toey-ness may get the better of you and you end up boning him – this isn’t so bad if he is interested in you, but if he isn’t, there is a strong chance that you’ll be Monday’s topic of the day in the office kitchen and it wont be because of the outstanding sales presentation you made last week if you know what Chuck means.

A completely left of centre idea is to wait until Christmas time rolls around. Most offices do a ‘Secret Santa’ where people secretly buy presents for others in the office. Now the person you are buying for is typically drawn from a hat. In this instance, you’ll need to be a bit sneaky and just buy an additional gift for this guy. You want to get something that suggests that you are interested in him and this should have the effect of getting him to start sniffing around the office trying to find out who the mystery shopper was. Chuck suggests subtlety and perhaps a little note indicating a level of interest. Try and avoid wrapping up a tube of KY and a thumping foot long dildo with a note saying “you – me stationary cupboard” as that may unsettle him.

If you’re prepared to put a little time and effort in, Chuck suggests that you try initiating lunches together once or twice per week. That way you can try the old “we were really good friends before anything happened” trick (which when Chuck thinks about it is probably one of the best ways to land yourself a long term partner anyway). During these lunches you can get to know him, talk about yourself and of course figure out whether or not he actually wants to run a length through you.

Once you have the lunches working, then you start working in the after hours drinks. At first you probably want to pull a few of the work crew along – safety in numbers after all. You need to evaluate his willingness to go along. If he is a raging alcoholic, you’ll soon find out because he’ll be the first guy to put up his hand. What Chuck means is that you need to start hinting that you’ll be in attendance and see if that sways him.

It’s easy to pump a few drinks into him, but a really skilled practitioner gets him to stick around once people start leaving and the numbers dwindle. Its when you can get him out on his own on a school night that you’ll really get a feel for him. Of course your work will likely suffer because you’ll be tired and hung over but most bosses will understand if you tell them you were trying to score some crank shaft.

If you get really desperate and he just isn’t getting the hint, then you need to start inviting him along to things that can easily be considered both dating and friendship events. The reason for this, is that if he is a moron and cant tell that you are keen on him, you can avoid losing face (both internally and in the office) by saying that they weren’t dates, it was just two friends hanging out. HOWEVER, these are also activities that easily allow the switch to be flicked. For example, a night at a comedy show can easily go from a ‘friends get together’ to a ‘date’ simply by sharing some laughs, a couple of drinks and a pizza. Before you know it, you’ll be pashing on while the comedian openly mocks you for cheap laughs.

The downside to the whole becoming friends first approach is that once he gets comfortable, if he isn’t really interested in you he’ll likely start crying on your shoulder about the woman who is currently treating him like he is treating you. He’ll be seeking advice and ego stroking from his new female BFF. If you had a set of testicles, this is what it would feel like to be kicked in them. The pain will be compounded significantly if his unrequited love happens to be the snotty bitch that sits across from you at work!

Or you could just ask the fucker out.

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