25 Ways to Approach A Woman At Work And Not Get Sued

Monday, November 19, 2007 at 4:43pm by Site Administrator

It isn’t any surprise that coworkers often find themselves attracted to one another. After all, you’re working in close proximity, seeing each other regularly, and usually dressed more attractively than you would be in a more casual situation. Yet work romances can create a troubling dilemma. Many businesses  have strict rules about what is acceptable when pursuing a romance with a coworker, and for a good reason. Often, there is a fine line between what is harmless flirting and sexual harassment, and underestimating it can cost you your career. So if you want to ask out that cute girl from marketing, follow these tips to avoid landing yourself in hot water.

  1. Ask her to lunch. Lunch is a relatively harmless request, as business associates often get together for lunch to discuss work related issues. If you’re nervous or want to be extra careful, invite along a few other coworkers.
  2. Send her emails. Sometimes emails can be a low-pressure way to ask out the object of your affection at work, and she won’t feel like she has to give you an immediate response. Just be careful what you write–emails are often monitored, and any inappropriate emails will likely be saved for your dismissal interview.
  3. Include other coworkers. If you’re afraid to risk it all and ask her out one-on-one, try inviting her out with a group of coworkers. You’ll still get to spend some time with her away from work, but there will be other people around to ease any potential awkwardness.
  4. Only ask once. If you’ve asked her out and she said no, don’t press the issue. Repeated attempts at getting her to go out with you will make her uncomfortable and definitely cross the line to harassment.
  5. Give non-threatening compliments. One way to show your interest in a female coworker is to pay her compliments. You just have to be careful about what you say, as there are many things that could be taken in the wrong way and could sound inappropriate. One way to do this is by giving a compliment accompanied by a question such as "That’s a nice University of Whatever scarf. Did you go to school there?" That way, she won’t feel pressured to respond to your compliment, and you’ll get to know a little more about her.
  6. Walk with her to meetings or out of the building. Make the most of your travel time through the building to spend time with the woman you’re interested in asking out. It’s an easy way to approach her and it’s unlikely to make her feel uncomfortable because your walk has a terminal point.
  7. Arrange outside of work outings. You won’t seem like a creep if you ask her to come along on company outings outside of work, and in fact, if she’s new you might even score some points with her for making her feel included in the group.
  8. Keep your distance. While you might get away with getting touchy feely when approaching a woman at a bar, at work you should keep your distance. Don’t invade her personal space. Instead, express your interest through your face and body language.
  9. Tell her jokes. Jokes can be a great way to get her to let down her guard and think of you as a person, not just her coworker. Just be careful to keep the jokes clean to avoid upsetting her or any other coworkers within earshot.
  10. Bring her coffee. Provided she likes coffee, this will be seen as a sweet, non-aggressive gesture. If you’re lucky, you could turn a one time gesture into a daily coffee date.
  11. Only approach those who are not your subordinates. It doesn’t matter how attractive your subordinates might be, they should be off limits if you want to avoid future trouble. Even if you spark a long-term relationship, if it goes sour you could become subject to complaints that you used your status as leverage.
  12. Make excuses to stop by her desk. Walking by her desk every once in awhile or bringing some papers over to her can be a good way to break the ice and give you an opportunity to ask her out.
  13. Keep it casual. If you do ask her to go out, make sure it’s something that isn’t too intimidating. Try asking her to get coffee or dinner before asking her out to come over to watch a movie.
  14. Be her friend first. Before you take the leap to asking out a coworker, get to know her first. You may find out that while you thought she was cute, you two don’t really have much to talk about. Of course, if you do, you’ll have a much easier time asking out someone you’re already friendly with.
  15. Send her a meeting invitation. Why not get cute about it and send her a meeting invitation through her email? You can keep things casual with a simple catch-up lunch meeting if you want to see how interested she is.
  16. Ask for her help on a project. You can often approach a coworker you don’t know particularly well by asking for her help on a project. You’ll get her help and a chance to talk with her that you might not have otherwise had.
  17. Take breaks together. Invite her along on your afternoon snack run or trip to the water cooler. If she says yes, who knows, she might say yes to dinner and movie.
  18. Use work as a conversation starter. An easy way to break the ice with a coworker is to joke around or talk about work. You can share a laugh about how sweaty your boss was at the meeting or how awful the coffee is in the break room. You’ll be bonding, but in a way that’s appropriate for the office.
  19. Leave her outs. If you want to ask out someone from work but you aren’t sure of her interest in you, make sure you leave her an out when you invite her on a date so that she doesn’t feel trapped or made uncomfortable by your request.
  20. Get her opinion. If you work closely with the coworker you’re interested in, try asking her opinion on something you’re working on. It’ll let her know you value what she thinks and later on, you can ask her opinion on more personal matters as well.
  21. Gauge her interest. Whether you ask around the office to see if she might be interested or just read her signals, don’t pursue a woman that doesn’t seem to be into you. While this is a good rule to follow in general, it’s especially true for the office.
  22. Save her a seat. One way you can show interest in a woman at work without being too pushy about it is to save her a seat at your next meeting or conference. It’s a nice gesture and you’ll get to sit by her the whole time.
  23. Ask her questions. You’re unlikely to face any lawsuits for trying to get to know a coworker better, unless of course you start quizzing her about her personal life or dress sizes, so take the opportunity to ask her questions and get to know what makes her tick. It will make it easier to ask her out later.
  24. Maintain eye contact. This is a good approach to dealing with women at work, as it shows that you are interested in what they are saying. It also makes it clear that your eyes aren’t wandering to places that are inappropriate.
  25. Just ask. Sometimes the best way to approach a woman at work is to just do it. That way, you’ll know right off the bat if she’s interested or not, and you won’t be tempted to say or do things that she might find harassing if she’s not interested.

Remember that none of these tips are foolproof–every person has their own comfort threshold and some might take offense at things of which others would think nothing. Stay smart, and who knows? Your office romance might blossom into something more.

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  1. I’m sorry, but this is totally irrelevant. I come here for great business advice, not to get tips on getting dates at work. I can read esquire for that. I want to continue to subscribe and read the site, but I want the content to be on topic.

    Comment by Isaac Luria — November 19, 2007 @ 7:50 pm

  2. interesting list. makes a lot of sense tho.

    Comment by Israel — November 20, 2007 @ 5:13 am

  3. HELLO,


    Comment by Brett Yenzer — November 20, 2007 @ 6:24 pm

  4. Hi,

    These instructions are a sure way to get you in to hot water. I’m not surprised that this advice is given by a WOMAN. I am in senior management. Bringing her coffee or making compliments will lead to some type of complaint. Dating a coworker is detrimental to a guy who’s successful. Why loose all your hard work and dedication not to mention years of going to college. There are plenty of women around. Women are increasingly becoming vindictive. Why destroy your career for a female. I recently fired a woman who kept on being aggressive to another co-worker; her argument to our surprise was that she was a woman and felt harassment only applied to men (what BS). I guess workplace laws are slowly changing to realize that women are equal contributors. With the EEOC rules and WAVA, women have become unstable, emotional, and weak. I advise men and women that I won’t tolerate any harassment. The bottom line is that a company is an entity and it can be sued by a man or a woman. I have no problem being neutral and finding the facts to kick the liability to the curb!!!! You should advice women on how to behave too!!

    Comment by Frank Debolt — November 20, 2007 @ 6:38 pm

  5. Never, Never, Never,approach a woman in the work place. It will always backfire on you. Women in today’s workplace are not only wolves but mentalally inbalanced. Forget it, go to your local brothel or street walker if you need it that bad. It will cost you less money, less headaches,and you will keep your professional reputatation at work clean.

    Comment by Stonecutter — November 20, 2007 @ 8:46 pm

  6. Unfortunately, I went into management positions after getting out of the Army, and anyone I was attracted to in American corporations was my subordinate.

    I was not happy with the new laws that made it so I simply had to forgo starting any extracurricular relationships, despite seeing green lights. There was too much to lose careerwise and money-wise.

    In foreign countries, men mostly don’t have this risk scenario.

    Comment by Jim Peterson — November 20, 2007 @ 9:59 pm

  7. “Often, there is a fine line between what is harmless flirting and sexual harassment, and underestimating it can cost you your career”

    Question: WHO determines where the fine line is that will ruin my career?
    Answer: she does, subjectively. So my future rests on the shifting sands of female discretion.

    Sorry Princesses, that won’t work for me.

    Comment by JR — November 21, 2007 @ 1:06 am

  8. This is such BS. This advice is given by another woman! Avoid women like these and stay away from these female losers who will destroy your career. Get a woman outside of work. WOMEN are full of it!!!!!!

    Comment by David — November 21, 2007 @ 1:51 am

  9. No need to wonder why more and more men are rejecting American women. No need to follow their rules. There are over 50 million marriage-age women living in countries south of Mexico. Its a no-brainer.

    Comment by Mack — November 21, 2007 @ 2:59 pm

  10. Short answer:

    Don’t date approach women at work, ever.

    If you value your job, avoid at all costs.

    Women have all the Rights, and you are one bad mood away from her endind your career.

    Comment by Lee — November 22, 2007 @ 12:28 am

  11. why did you remove my comment? That is chickenshit. Read your own article, it’s getting to the point where you have to ask a lawyer to sign off on any approach toward a female…in fact, legally American men DO have to get legal approval to contact foreign women (IMBRA). Under those circumstances many men will simply drop out of the game…and fly to Thailand for the holiday. It might also be interesting to ask what is the relationship between the rise of the Mommy State (with it’s myriad rules) and the decline in US global competitiveness. Mommies didn’t invent stuff like light bulbs, transistors, CAT scanners, or airplanes. If you are a man, then get some balls. If you are a woman, you need to put them away, they do not belong to you.

    Comment by JR — November 22, 2007 @ 10:07 am

  12. Why should I want an office romance in the first place ? In my country prostitution is luckily legal so it is nothing of the back alley thing going on in the us and as for long therm, she is obviously married to her career. With a working woman you are damned if you do and damned if you dont. If you dont provide enough shes gonna resent to not have a “real man” at home. If you do provide and she stays home maybe because she is a mom shes gonna miss work and will resent you and your evil *e**s that got her pregnant. Just avoid career women or even women who are happy at work and not exactly planning on becoming a housewife in general.

    Comment by Marco — November 22, 2007 @ 2:07 pm

  13. It’s very simple: Do NOT approach women at work, period.
    Never. In no circumstances.
    You are putting yourself and your career at the mercy of her future moods.
    You are taking unneccessarily big risks for something that can be easily obtained elsewhere.
    Just do not do it!

    Comment by Leopold — November 25, 2007 @ 5:38 pm

  14. Your censorship is a textbook example of the repression you so clearly describe in your “article”. Honeybuns, real men do not live by female rules, nor do they seek a lawyer’s approval before approaching women. No wonder the US is declining, tell me what women have done besides carry eggs? Invented the car, computer, light bulb, penicillin, TV, X-rays, airplanes, or Oreo cookies? Duh, not. I’m 52 and I will bang the hell out of my 25-yo girlfriend tonight in your honor!

    Comment by JR — November 25, 2007 @ 10:59 pm

  15. I would like to talk to you about developing this a little more with some examples what not to do and possibly adding it as a resource to my Men’s Inquiry web site. You can contact me at [email protected] Thanks! Martin

    Comment by Martin Brossman — November 26, 2007 @ 2:02 am

  16. This article illustrates the absurdity of harassment law. I call it the Brad Pitt contradiction. Suppose two men, one a normal fellow and the other Brad Pitt, engage in EXACTLY the same activity in pursuit of romance with a woman at work. The acts of the normal fellow can be harassing while EXACTLY the same acts by Brad Pitt aren’t. Why? Because the law defines harassment by the emotional effect on the woman, not the objective acts of the man.

    All 25 points, listed by Ms. Laun, can be cause for a harassment action. For example, apply the Brad Pitt test. If Brad Pitt maintains eye contact (no. 24), it’s romance. If the normal guy does it, it’s creepy harassment.

    Anything can be harassment. Anything. At law, men are held hostage to the fickle emotional states of women. That’s unjust.

    Comment by Jeff — November 26, 2007 @ 4:47 pm

  17. Where were u when I was 15??

    Comment by Scott McArthur — November 26, 2007 @ 11:46 pm

  18. LOL you Americans are so funny. And all those comments saying that a woman is not worth risking your career or money. Seriously, get a life people.

    Comment by European — December 1, 2007 @ 10:35 pm

  19. Jeff, you are so right. If the woman thinks you’re cute, then you can do no wrong. If she thinks you’re icky, then you’re one step away from a meeting with HR. It doesn’t matter what you actually did, the only thing that matters is how she feels about you.

    Comment by Eric — December 2, 2007 @ 6:21 am

  20. Christina Laun,
    Are you actually f—–g serious? Any man with all his mental faculties intact knows that this advice is essentially how to commit suicide.

    Oh and by the way “European”, this is about life in America. I know it sounds like “we have to get a life,” but this is our reality.

    Comment by DannyM — December 8, 2007 @ 10:00 pm

  21. An additional comment: Why on earth would I try for “that cute girl in marketing” when there are tens of millions of cute women outside the walls of my workplace? (BTW, I live in Los Angeles.)

    Comment by DannyM — December 8, 2007 @ 10:03 pm

  22. Jeff is 100% correct. My own sister told me it all depends on how cute is the guy.

    Comment by Joe MaMA — December 12, 2007 @ 9:40 pm

  23. Wow. I guess it’s just as well that some of these commenters prefer to keep their distance from the women in their offices. Those women probably thank them.

    At last, though: etiquette for outlaws. There’s some good stuff here.

    Comment by Kathleen — January 10, 2008 @ 1:11 am

  24. Stay away from women at work, as she has the power and benefit of the doubt for her. The employer will fire the man first, as there are no federal or state government agencies or courts that support him (Think of the Duke student’s false rape charge by a whore, without the media attention).

    If your a guy, it would be wise to stay away from woman in the family too, as when she divorces you (unilateral, no-fault, 50% divorce rate), though the man is legally innocent, he will lose his children, home, 18 years of income, and certain liberties.

    Read “The Tyranny of Tolerance” by a sitting judge. He would lose his job if he supported a man and not a woman. Feminism (man bad, woman god) is the rule of law.


    Comment by Markr — January 13, 2008 @ 10:42 pm

  25. I am astonished at the comments made about women and the workplace in this blog? To quote “unstable, emotional and weak” and “mentally imbalanced”. If these are your true opinions, you should most certainly avoid asking out women at work. You will be throwing your career down the tubes. For those men with a genuine respect for women and an appreciation for the value we bring, the result will be much different. The advice above will be flattering to a woman and will most likely win a friend if not a date. Your attitude determines your altitude. If your attitude is one of respect, the result will be respectful as well.

    Comment by Theresa B — February 3, 2008 @ 3:33 pm

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