How to Date Women at Your Work Without Catastrophe

January 10th, 2013 by Nick Notas 9 Comments

Jim and Pam Flirting

At some point, you’ve probably been attracted to a co-worker. I have, and I know how it feels when you start to think, “Damn, she’s really hot…but is it worth it?”

Everyone will tell you to “never fish off the company pier”. In theory, they’re right. Dating a co-worker is a touchy and a potentially dangerous route. But this is the real world where our feelings aren’t black and white. It’s easy to make that call from an outside perspective.

What about all the relationships and marriages that have stemmed from workplace romance? I know many couples that have done it successfully. One has been happily married for 25+ years with two wonderful daughters. Hell even cast members of Scrubs did it.

How different would their lives be if they listened to the naysayers?

The goal of this article is not to convince you whether you should or shouldn’t hit on a girl at work. It’s to provide the tools to help you properly evaluate the situation and make a choice. If your decision is to go for it, then I’ll show you how to maximize your chances of success.

Evaluate the situation wisely

Do you have a specific girl in mind? Answer these three questions:

How much do you care about this job?

Understand that if something goes wrong it can make things very awkward at work. Even worse, you could lose your career or face legal action.

If you work at Chili’s, this might not matter as much (unless you’re a manager). But in a corporate or business environment, you have to proceed with caution. It gets trickiest when the two of you are on different tiers or if you’re in a direct superior position.

Has she shown interest in you?

Has she tried to start conversations with you often? Does she hang out with you more so than other co-workers? Has she invited you to do something outside of work? Does she compliment you regularly? Has she made any obvious flirtatious or sexual advances?

I always advocate that you shouldn’t wait for a woman’s signals to make a move. Much of the time you won’t get them and you’ll miss out on great opportunities. However, they can be a useful litmus test and influence your decision to move things forward.

If she never talks to you or acts cold, your advances may not go as smoothly as you hope. It may be better to talk to her first, see if she warms up to you, and then ask her out. Now, if she’s made it abundantly clear that she likes you, you can proceed with minimal risk.

Why are you trying to hook up with girls at work?

Is it because you don’t actively meet other women? Are you only chasing a co-worker because it’s convenient? Or do you legitimately feel a strong connection with this girl?

If you think she’s worth the risk and your intentions are healthy, go for it. But keep in mind there’s a whole world of women outside the workplace. They want to meet you.

Increase your value in the workplace

You should strive to be your most attractive at all times. Coincidentally, this will ensure that eligible women view you as a charismatic, accessible man.

Dress with style

Good fashion conveys that you hold yourself to a higher standard and take pride in looking your best. That attitude is attractive. Lucky for you, you don’t have to try hard to stand above most men at work.

The average male employee falls into two categories: either he dresses down because he doesn’t care or he dresses up in lame, boxy, oversized business attire. You should still dress business, but fitted and stylish. Think “sexier” modern brands like J. Crew, Banana Republic, Zara, or even H&M (on a budget) rather than Jos A. Bank or Men’s Wearhouse.

Not only does dressing well make you attractive to women, it makes you attractive to employers. Good-looking people get more opportunities and promotions, it’s a harsh reality. And as your status raises, so will your attention from women.

You should primarily want to look good for yourself. But it doesn’t hurt that it increases your chances across the board.

Build powerful social proof

Engage your co-workers. You don’t have to become the work clown but being social and having friendly conversations are important. When you have a group of work friends, your social circle makes you intriguing and valuable.

If she sees everyone enjoying your company, she’s going to want to be a part of that as well. She’ll perceive you as someone worth knowing. “Wow, he must be cool if everyone likes him. I should introduce myself.”

Finally, when people like you, they’ll willingly introduce you to new women. Not only that, but they’ll throw in a good word, too. A warm social introduction is one of the strongest ways to start a connection.

Be a source of positivity

We all bitch about work sometimes. Too often, we are consumed by that negative energy and it becomes all we talk about. Unfortunately, nobody wants to be around someone who’s gloomy and always brings down the mood.

Even if the girl you like tries to complain with you, don’t jump on it. While it may seem like a good idea since it gets you both talking, it will hurt you in the long run. You’ll become just another co-worker that she can vent to. She’s not going to feel romance when you’re rehashing how much you hate your job.

Elevate yourself over the drama. You should be the guy that gets her to forget the stress of work and life. Wear a big smile and laugh with her often. Relieve her stress through positivity and she’ll associate you with being happy.

Take action and responsibility

Before we discuss taking action, I need to address a point on physical escalation…

Tread carefully with your physical contact in the workplace. As critical as touching normally is, unwanted advances can lead to some serious repercussions. Wait until you get her out of the office.

The only exception is when she starts touching you first. For example, if she hugs you or playfully pushes you, you have a better chance of returning the same and being received well. Still, I would be extremely cautious and consider waiting. There’s a lot of risk involved, including office gossip or having a falling out where she accuses you of sexual harassment. It ain’t worth it.

Invite her out ASAP

You aren’t going to hook up with a girl while in the office. Okay, well you could but it’s unlikely and very risky. Instead, your objective should be to try and get her out of the workplace.

There are two main ways to do this:

  1. Invite her to an after-hours activity with co-workers.If a group of you already have plans, ask her to come along. This is best used when you haven’t talked much or gotten to know each other. She’ll feel encouraged to say yes since everyone’s going.

    The downside is you’ll still have to keep it relatively friendly. You aren’t going to make many advances in front of co-workers and she may feel uncomfortable if you do. Instead, you can have an awesome time together, strengthen the connection, and build trust.

    Once you’re alone for a moment you can flirt a bit, suggest hanging out together another time, and get her number.

  2. Invite her to hang out one-on-one.This is best used when you’ve already talked a couple times and have built some rapport. Approach her privately (on lunch break or in office when alone), talk for a few, and suggest a casual hangout. “Hey, so I’m going to my favorite cocktail lounge tonight/tomorrow/Thursday. You should join me for a drink.”

    If she’s down, exchange numbers. If she’s hesitant or doesn’t suggest a better time, respond with a smile, “No problem, maybe another time.” You can try again a few days later but if she’s not making an effort, she’s probably not interested.

Finally, if and when you do get her out, treat it like any other date.

Handle with care afterwards

The most important part about all this is handling what happens after.

If you start dating, it’s only a matter of time before your co-workers know. Keep it professional. Respect her privacy and don’t dish out the gritty details to your friends. Also, too much flirting makes some people uncomfortable and reflects poorly on your career attitude.

If she rejects your advances on the date, simply let her know you misread the situation. Be mature about it and stay amicable at your job. She won’t make it a big deal if you don’t.

Have trouble making the first move? I can help.

  1. Aaron on January 11, 2013

    You know, I think I’d built up asking a cute girl out at work, after reading this I don’t feel as worried about it…if she says no do I just kinda give her space and go back to being friendly?

    • Nick Notas on January 11, 2013

      Aaron, that’s exactly it. As long as you don’t act weird or confront her aggressively about it, there shouldn’t be a problem.

  2. dew on January 11, 2013

    Perfect article for me right now. I work with a girl who I was considering asking out. I evaluted the situation and I’d like to proceed but I also work with both her mother and older brother. On good terms with both though. Any advice?

    • Nick Notas on January 11, 2013

      Damn, that’s a really tough call. If you’ve already decided that you want to move forward, you have to be extra cautious.

      You’re close with her family. Although I normally wouldn’t do this, you might want to let her brother (or mother) know beforehand. “I’m thinking about asking Mary for a drink on Thursday. I wanted to let you know and make sure you were okay with it.” See what the reaction is.

      Because if you just go and ask her, you could piss her family off. They might feel slighted. And if they don’t want you two dating, it could cause serious problems at your job. It’s better to know beforehand.

      If they do want you to ask her out, they’ll be your biggest supporters. You can tell them to not say anything because you want it to be a surprise. Then go talk to her and move things forward.

  3. Vichet on January 11, 2013

    Hey Nick,

    Great read!

    Another couple of notes – you should definitely address that some companies have anti-fraternization policies, or at the least disclosure policies where you’re required to inform management of this kind of thing.

    I know a few friends who have had to deal with this. Key point: know your workplace and its policies, the same as you’d know the etiquette and written/unwritten rules of any bar you’d frequent.

    • Nick Notas on January 11, 2013

      Hey Vichet,

      That’s a huge point that slipped my mind. I’ll probably make an edit later and credit you on the post.

      I’ve never worked at a place that had a policies like that but I know people who have as well. You definitely need to know your workplace policies or you’re setting yourself up for trouble.

      Thanks for the insight as always!

  4. Zack on January 13, 2013

    Hey Nick,

    Very timely article!

    I met this girl at work and we instantly got on; making each other laugh, etc.
    She then invited me to lunch. Over the next few days I get her number.
    I next meet her in a group environment and we hit it off as well. After drinks before parting our own ways, she kissed me. She then says I’m not that type of girl and suggests we go out on a date.

    I take her out the next day and it goes great; kissed her midway because I wanted to, etc.
    Our 2nd date goes even better as I’m more relaxed around her and spend the date enjoying myself and her company.

    On the 3rd date she doesn’t seem as comfortable around me. She wasn’t receptive to touches, backed away from the midway kiss (mentioned she isn’t into public display of affection. I know this from the 2nd, but this was a bar..). She did kiss me before the date ended though.

    Next day I get a text from her saying she had fun, but would prefer to keep it as friends if that’s okay. That shes still getting over someone, and that she would still like to hangout as friends if I’m up for it.

    From work I know there is truth to the ex element, but if you like someone then you like someone, ex or no ex. So I’m wondering if I came on too strong (3 dates within 3 weeks). How do I let her know in a non desperate way that I’m perfectly fine with taking things really slow and just showing her a fun time.

    • Ethan on February 5, 2013

      Nah dude you didn’t come on strong enough. If you really liked her and are open with your own sexuality, you would’ve been way more on her on the 1st and 2nd date. It sounds like you analyze this shit too much and are in your head way too much. I’d suggest learning to get in touch with your feelings/emotions so you know the next time you are turned on and attracted to a girl to act on it.

  5. Sam on March 13, 2014

    Hey…tough one
    I keep hearing the don’t shit where you eat and don’t screw the crew talk about dating someone from work but it hasn’t stopped me from thinking about it but anyway…
    I work for my dad in a small bakery as a pastry chef and we have female shop assistants, over time I’ve become quite attracted to a girl who has been there a while but recently I have gotten to know her better and would consider asking her on a date but not sure on the response…being the bosses son and all would it make her feel more awkward if she’s not interested, I don’t want to put her in a place where she may want to leave…she’s 21 I’m 20 not that it bothers me but also not sure if it would bother her, any advice would be appreciated!


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