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Ask The Good Enough Guy: Should I Flirt With The Office Cutie?

Hi Will:

I love my job.  I’m good at it and I’ve always gotten compliments on my performance. Well, a few weeks ago, we got a new coworker. Oh, he’s so gorgeous! He isn’t married or dating and he has all the women in the office about ready to lose their minds just to talk to him. I feel so lucky that he and I are working for the same manager which puts me in his path every day. But that’s also a problem. I can’t seem to keep my professional decorum when I’m around him. The fantasies I have of us “dating” have me flustered and I’m ashamed to say that I have missed a deadline or two just because I wasn’t paying attention and missed information when we worked one-on-one. I, of course, can’t quit my job nor do I want to, but I have to do something because this situation is making it difficult to work with him and around him. Help!

Hot and Bothered in Baltimore


Seriously!?  Wow. I guess spring fever gets us all. I mean, I’ve seen a new, attractive woman in our office make the guys go cuckoo for Coco Puffs and when I started my new job, all of the women here dealt with how stunning I was without any noticeable problems. Or maybe they just hid their desires really well. And I did start in the winter time, so that could be it. Either way, I’d answer your question with a question: So what are you waiting for?

FIRST THINGS FIRST: I can’t tell you what I’d tell a guy because the part of his anatomy that I’d accuse him of thinking with, you don’t have. So what I will say is, firmly grab the reality steering wheel and pump the brakes. This guy could be Brad Pitt and Idris Elba twisted into a sexy swirl, but his good looks won’t pay his bills, let alone yours. Once you’re at home, you can fantasize about “dating” him ‘til you shoulder gives out, but at work, you need to keep your mind on your company’s needs and your pay check. Good jobs are hard to come by these days and jobs we love, even harder. Try this: any time you two have to work together, picture your Romeo handing you a pink slip, taking over your job, and dating that loud mouth heifer that works down the hall from you. Kinda takes away from his sex appeal, doesn’t it?

GET OFF THE WALL AND DANCE:  As I said before, “What are you waiting for?” If a an attractive, single, woman starts in a new office, any guy who thinks he has a shot has already taken it before she finished her first cup of bad coffee. Unless your company has a very strict fraternization policy (most don’t), there’s no harm in you asking him out. Maybe you’re waiting for him to ask you. Maybe you’re too shy or too nervous to ask. Maybe you’re worried he’ll turn you down. Maybe you’re worried you’ll go out with him and he’ll turn out to be an ass. To all of that I say this: Would any of that be worse than listening to one of your co-workers go on and on about how wonderful her date was with him after she asks him out? What if he’s waiting on you to give the green light? You snooze; you lose.

WHAT IF HE SAYS NO? Well, at least you took a shot. That’s easy for me to say because guys expect to get shot down three out of four times and the odds are even worse if both parties are sober. He’ll give some excuse why it isn’t a good idea. You’ll say, “ just thought I’d ask”, and then never bring it up again. It may make things a bit uncomfortable for a few days, but it won’t be any worse than running around behind him like a school girl with a crush. And it will probably cause what I call, “the sour grapes effect”. It’s amazing how uninteresting a person seems once we find out they’re not interested. The day after he turns you down, you’ll realize that his eyes are too close together, his hands are too small for his body, and that he wears far too much cologne. After a week, you’ll wonder why you ever asked him out in the first place. Blame it on springtime and get back to work.

WHAT IF HE SAYS YES? Know your boundaries. Even if most businesses don’t flat-out prohibit office romances, no company wants a couple playing Naked Twister in the copy room. If he’s as hot as you say, there will probably be some hurt feelings amongst your female co-workers who may be all too happy to report any PDA’s that aren’t office issued. Remember: from 9 to 5, he’s a co-worker. After hours and off company property, do whatever comes natural, but don’t be late for work in the morning.

Now go for it. If he ends up being Mr. Right, send me a wedding invitation. If he turns you down flat, I’ll send you a pint of chocolate ice cream and Fabio voodoo doll. It’s a win-win!

Good luck!

More From GEM:

Our Story Begins: It’s A Juggle Out There

The GEM Debate: “Condoms? We Don’t Need No Stinking Condoms! We’re On The (Man) Pill!”

The GEM Debate: Is This Teacher In Love Or Out Of Bounds?

William Jones is originally from the tiny town of Alton, Illinois, and now lives in the tinier town of Reisterstown, Maryland. He is a happy husband and a proud father of three, and writes as a hobby, in those few moments he finds between husbanding and daddy-ing. Follow him on Twitter @goodenoughguy1.


  1. Deon smith

    April 14, 2012 at 10:28 am

    Respecting the boudaries is key as will stated in his final paragraph. There are tons of fish in the sea. In these times where jobs are scarce would one be willing to put their job on the line for temporary satisfaction? We are hired for our performance. The workplace isn’t a cruise bar. Very little good comes out these practices. Theses parameters must be adhered and respected at all times…that is if you value the blessing that is your job. PRIORITIES MUST BE SET.

  2. Hillery Shay

    April 14, 2012 at 11:39 am

    I’m a no go type of human. The phrase “You don’t $h-t where you eat!” comes to mind. Find an outside work fish and get your hormones in check. Work should be a place where you can be talked about for your professional nature not gossiped about for a failed fling. There are too many complications that could arise and good jobs are hard to find and even harder to regain footing on a new corporate ladder.

  3. Chris Lewis

    April 14, 2012 at 12:52 pm

    I would say don’t do it! Why? In the workplace there’s a fine line between flirting and some ding-dong feeling harassed. So in order to play it safe, if you did, it shouldn’t be during work hours! IJS 😉

  4. Will Jones

    April 14, 2012 at 8:39 pm

    I see lots of folks disagree with me on this one. Lots of my friends did too, but I say if we spend eight hours sleeping, eight hours working, and the remaining eight doing who knows what, there’s a pretty good chance we’re gonna meet compatable, date-able, people where we work. If you cut your office out of your hunting ground, you aren’t leaving many hours of your day to hunt. Just saying…

  5. Lashell

    April 15, 2012 at 8:25 am

    I have a rule…well many of them. LOL! One is I refuse to date any man I work with. If he works for the same company, but in another department, but asks me out…IT’S A NO!!!

  6. Will Jones

    April 16, 2012 at 8:02 am

    Lashell-Why not? I say if two people are adult enough to be in a lasting relationship, they should easily be adult enough not to let said relationship interfere with their work. Now, if a person knows they have a history of slashing tires, busting windows, and burning their ex’s clothes, that’s another story.

    Hillery- How is a date “$h-ting where you eat”? I’ve didn’t meet my wife where I work, but I hate to think that, if I had, we would have never gotten together simply becasue we worked together. And, no matter how low-key you try to keep things, some people are going to gossip about you anyway. Why miss out on a chance at real love because of what others might think?

    Deon- How can you know whether it is “temporary satifaction” or something much greater if you’re scared to try? I’m a big fan of proirities, but I think a person’s happiness should be should be at the top of that list.

    Chris- While I might agree that flirting isn’t the best idea (it was never mentioned in the question, and I didn’t title the article) asking someone out on a date is not considered sexual harrassment. Now if you do ask and are told no, that must be the end of it or it could be considered harrassment, but asking, in and of itself, is not.

  7. m.e. johnson

    April 17, 2012 at 8:06 pm

    Hi Will. I’ve been out of commission a few days, getting my hard drive replaced.

    Now, first I’d look for a sign he’s interested; he brushes a (non-existent) piece of lint from her shoulder. Or he un-necessarily touches her hand as he un-necessarily borrows her pen. Or there’s “the gaze” he lets you catch him at. There’s a million of ’em. Myself, I’d first wonder that if he’s all that and he qualifies for a position (not just a ‘job’), how can he not be already “occupied”. I’m interested in how things turn out for her.

  8. Will Jones

    April 19, 2012 at 10:27 am

    M.E.- That’s a good way to play it. Of course, she runs the risk of having someone else snatch him up first, but it does take a lot of the pressure off of her. It may be that he’s just shy, it may be that he’s too busy with his career to be looking for dates, or it may even be that he’s batting for the other team… but there’s still only one way to know. I’m interested too!
    (Glad you’re back; I missed you! 🙂

  9. Dave M

    April 19, 2012 at 4:13 pm

    Will, I have to say first, that I’m not sure if “dating ’till your shoulder goes out” or “Fabio Voodoo Doll” is my favorite line.

    I will admit on-the-record, though, that I met my wife at work. We worked together, peers, and she was gorgeous. But I also have to give the caveat that – when I realized she really was interested in me, too, all reservations and lack of confidence flew out the window for me. That’s when I knew she was perfect for me. I threw all my cares away and asked her out. We were engaged just a few months later.
    However . . . we also didn’t want to be like another couple at the same place, who had lunch “dates” together and met in a locked office, whole nine yards. We dated without telling anyone about it and at the office it was work and as soon as we left the building it was amazing! There were some hurt feelings, others liked Andrea, too, and it made things hard for a bit.

    But I was married to her for 18 years.

    My ? If you think he’s worth it, go ahead. If you’re just looking through hormonal or dreamy eyes – looking for a bit of fun or a fling – why do it? The repercussions are far bigger if it falls apart and you’re on the same team. But if you see this as bigger, like I did, there are ways to make this work. I know I’ll get the same grief you did, Will, but I wouldn’t change a single moment, particularly now. I didn’t give a damn about a single criticism once we let everyone know – which we did once we were sure it was going to stick.

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