Can I Ask a Colleague Out on a Date?


“Can I ask a colleague out on a date?”

I’d fire this question at my sexual harassment awareness workshops. Often, the room would go silent. Several faces would turn pale.

I would decide to put them out of their misery.


Barack met Michelle at a Chicago law firm. When he first joined, she was asked to mentor him. Image: Ron Sachs-Pool/Getty Images

By asking, you show respect. If it is a yes, then that’s consent. If it’s a no, then respect their decision and move on. Sometimes sexual harassment arises when you don’t ask and play those games – you know, the ones where you’d apply a light touch to see if she would flinch or reciprocate. Or make a sexual remark to see if there would be interest.

Now we are getting into dangerous territory. If you are really interested in a colleague, it’s better just to ask, “would you like to go on a date sometime?” or perhaps the less scary, “would you like to catch coffee after work?”

I’m not a dating advisor, and probably like you, am terrified of rejection – so I’m not going to advise how to ask a person out and save face. It isn’t about your dignity. It’s about the dignity of the person you’re inviting. How do you ask someone out without sexually harassing them?

Will HR Let You Date?

Before you start screaming at me, HR (Human Resources) is really not interested in your love life. But it will intervene if your relationship with a colleague impacts the work environment.

Check your workplace policies. Most organisations would frown on a boss and subordinate dating. As objective as you think you are, the rest of your team are still going to think you’re giving your boyfriend a favourable rating. Perception matters. Romance within a department, particularly if it’s small can cause not just tension between the couple but among the whole team. It can turn toxic. If one of the couple has to leave the department, it’s almost always the more junior person.

In one workplace I know of, a human resources manager intervened when several employees complained that a team leader was dating one of his subordinates. By this stage, the couple had broken up but the manager had to keep a sharp eye on his performance appraisal of her. There was a danger he’d mark her down if the relationship had turned sour.

There are times when asking a colleague out can turn nasty and is sexual harassment.

What IS Sexual Harassment?

If you don’t know, you’re not alone. Most people (including HR) don’t know exactly what constitutes sexual harassment, sometimes causing unfair decisions. Here’s the UK definition:

Sexual harassment is unwanted behaviour of a sexual nature which:

  • violates your dignity
  • makes you feel intimidated, degraded or humiliated
  • creates a hostile or offensive environment

The definition is similar around the world. Note that the definition is from the point of view of the harassed person, not the harasser.

The key here is “unwanted behaviour”. If a colleague asks you out, you have the opportunity to say no. As long as your dignity was not violated, you did not feel intimidated, degraded or humiliated; and there is no hostility after you said no. An example of hostility is where your colleague retaliates against you at work because you have turned him or her down.

You might ask – how would I know if my behaviour is unwanted? I will write an article in this #QUASH series on how to tell if you inadvertently sexually harass someone, so stay tuned.

If the concept of sexual harassment is new to you, you might not know. So I’ve listed 4 instances where asking a person on a date is sexual harassment.

When it IS Sexual Harassment

  1. You are his boss or in a position of authority over your colleague
  2. You won’t take no for an answer
  3. You use work as a pretext, giving the person little space to refuse
  4. You don’t respect the person, but rather see her or him as a sexual object

1. You’re the Boss

This is a biggie. Power dynamics is a primary factor of sexual harassment. Because you are in a position to determine his or her career path, it is harder for the person to say no to you. Sometimes they may say yes, just so they don’t upset you.

You don’t have to be a direct boss or even in the same department. You could be a client, an investor or a director on the board. You could be in a position to influence whether he gets the job, business or funding for his company. If he thinks you have the power to influence his career and responds out of fear, it is harassment. What if you didn’t have the intention to use your power? After all, he’s such a nice young man and you just want to enjoy his company for the evening. It doesn’t matter. Your intention is irrelevant. If he feels threatened and feels that to refuse could affect a pay rise, you have sexually harassed him.

Sexual harassment by a person in authority is far more serious than one between peers. There is the element of abuse of power. We call this sexual coercion. 

Last month, Lord Lester resigned from the House of Lords as he had been found by the privileges and conduct committee to have sexually harassed a woman (who later revealed herself as activist, Jasvinder Sanghera). They had both been working with a parliamentary committee on legal reform, relating to forced marriages, attending meetings at Westminster. Here’s an extract of Sanghera’s statement:

“As we were approaching the House of Lords building, he pointed to it and said “do you see that building”, to which I replied “yes”, he told me that it was the most powerful of decision-making. He said, “if you sleep with me I will make you a Baroness within a year”. He even spelt it out putting my surname in, and asked me how that sounded. I responded immediately without hesitation by saying that if I were ever to become a member of the House of Lords, it had to be purely on merit… 

“The impression he conveyed was that he was a man of power who could make things happen and that I was powerless in comparison…

“Once we had reached a private space and were not in full view of anyone he asked me again if I would sleep with him and suggested that I took some time to think about it. Again, I said no. He said that if I did not, he would see to it that I never had a seat in the House of Lords and warned me that there would be other repercussions for me, which he did not specify. He said that if I was a “good girl” and did what he was asking, I would be in the House of Lords and could visit his house abroad with him. He made a number of further inappropriate sexual comments to me such as that he could see me becoming a demanding mistress. I was distressed and shocked by his behaviour.”

Sexual coercion can either be an incentive – “if you sleep with me I will make you a Baroness within a year” or a threat – He said that if I did not, he would see to it that I never had a seat in the House of Lords and warned me that there would be other repercussions for me, which he did not specify. In Lord Lester’s case, we see both.

2. You get a “no,” but keep on asking

Frankly this is irritating for many people. No means no. Don’t think that he or she is playing hard to get. If they like you, they will say yes.

The following responses do not mean “yes”:

  • “I’m washing my hair tonight, and tomorrow night.”
  • “It’s really very kind of you to ask, but I really don’t have the time.”
  • Giggles, stares at shoes, “er, I’m not sure.”
  • “I don’t think my girlfriend would like it.”
  • Ignores you completely and buries head in laptop.

I had a case where a young guy was harassing most of the single ladies in the office for dates. Only one said, “no, go away.” He never harassed her again. The others, not wanting to hurt his feelings, gave excuses, and continued to give excuses. He just didn’t get the message. They complained. We had to warn him.

Want a clear way of knowing how the person is interested? They said yes, and look genuinely happy about it. If you don’t get a yes, stop. Don’t ask again.

“It’s not like you ask permission to grab your colleague’s private part. Just asking for a date.”

Megat Hanis, young activist

If you have a huge crush on a colleague who doesn’t reciprocate, I do feel for you. Confide in a friend. Get help. You need support so that you can get back to the business of doing a good job and not acting stupid in front of the Beloved. If you still try to win him or her over, you do run the risk of harassment and with it, your career.

The Hollywood idea of romance (up till recently) has given a very wrong idea of how to pursue the girl (or guy). Especially in an office setting. If you are interested in a colleague, you do not pursue them. That’s predatory. They are not your prey. Which brings me to the next no-no.

3. You Use Work as a Pretext

The workplace is not a hunting ground. You go to work, to work. Not to find sexual partners. If that’s your intention, you shouldn’t be there.

Weinstein’s predatory antics are now well known. He called actresses to his hotel suite on the pretext of discussing potential roles. His intention was sex, and to display his power.

Before #MeToo, the New York Times broke the stories of sexual harassment in the Silicon Valley. Male investors would ask women entrepreneurs to meet them in cafes or bars on the pretext of discussing their funding requirements. Upon getting an invite, the women would go armed with investor packs and business plans, ready to discuss their venture. Imagine their disgust and horror, when over the course of drinks, it became clear that the men wanted them sexually and had no interest in their venture. Or worse, dangled the prospect of funding – in return for sex. Because it could jeopardise future prospects for funding, it was difficult for the women to speak up.

“I felt like I couldn’t speak up at the time, or even tell Khailee [fund manager] about it, because we had the Distro Dojo deal at stake and we were supposed to sign an LOI that week. I was extremely conflicted about it. On one hand, I was really upset with Dave’s individual misconduct and never wanted to work directly with him ever again, but on the other hand, if I said anything, I would most certainly kill the Distro Dojo deal. The deal wasn’t even for a personal benefit (if I were raising funds for my own startup, I wouldn’t have taken his money), but it has widespread regional impact. It was so important to Southeast Asia that Distro Dojo be established there.”

Cheryl Yeoh , founding CEO of MaGIC in Malaysia about Dave McClure, former CEO of 500 Startups who sexually assaulted her. 

The line, “let’s discuss this project somewhere where we can be alone,” can be really unnerving to a woman who senses there is more on his mind than just the project. It puts her in a quandary. She wonders if she is being paranoid. After all, what if it’s just work and he wants somewhere quiet where they can focus without being disturbed?

In our workshops, we ask participants whether the words, “let’s discuss this over dinner when we can be alone,” was acceptable. It often attracts debate. It’s contextual. If two senior managers never have time to discuss strategic direction because they keep getting caught up with day to day business and meetings – dinner together is a welcome relief. But if a boss says say this to an executive during appraisal time, that is clearly not ok.

Draw the line. Work means work. If you are interested in someone, don’t hide it behind work. Be clear. It gives them the agency to say yes, or no. They can’t say no if you use work as an excuse. You’re disempowering them.

“He was trying to pick her up within the confines of work. She can’t escape from that”.

I watched the BBC3 documentary, Is this Sexual Harassment? last night. A group of young people were invited to watch a video and discuss whether there was sexual harassment. The scenario – two co-workers working at a bar. One of the young men watching remarked that, “He was trying to pick her up within the confines of work. She can’t escape from that.” He added that it would have been perfectly fine if he had invited her for a drink or meal, or a date outside of work. The women in the group agreed wholeheartedly.

4. You don’t respect them

How you ask your colleague out is also important. If you merely view them as a sexual object instead of a person, they will feel those vibes. Of course if you both want just a fling, then go ahead. You agree on the boundaries and respect each other. Disrespect is when one views the other as a lesser person.

Note that I am referring to flings or relationships where there are no power dynamic complications and HR isn’t going to come down on you because of a conflict of interest.

Here’s some pointers as to whether you are being disrespectful (with sexual tones):

  • would you be upset if someone said or did the same thing to a family member or close friend?
  • would you say or do it to someone of your gender (or if you are gay, to the opposite sex)?
  • would you say or do it to your boss?

If you answered yes, to any of the above, stop and apologise. You may not be forgiven, but it could make a difference. Better still, think of these three points before you say anything. Be mindful of your words and behaviour.


If you like someone at work, by all means, ask them out. But do so with full respect and mindful of the pitfalls I’ve described. Some office romances have a happy ending…

“Cuz kinda how I found my wife :)”

                                                                       Hisham Hamzah, educator

This article is the second in our #QUASH series (Questions About Sexual Harassment) which is a weekly column by for 2019. The first one answered the question: is sexual harassment a crime? We are inviting questions about workplace sexual harassment and will answer them throughout the year. If you have any questions, you can ask them on LinkedIn or send them to Speak Up At Work on FacebookTwitter or the Speak Up website.

#QUASH is led by Animah Kosai with a collective of experts on workplace sexual harassment issues – currently in the UK, US and Malaysia. If you would like to join our collective, please contact Animah through LinkedInFacebookTwitter or theSpeak Up website. We welcome advocates, HR personnel, psychologists, counsellors and anyone who has experienced sexual harassment and is passionate to make a difference.

Animah Kosai was formerly a Malaysian practising lawyer, worked in Oil & Gas and is currently researching on why people do not speak up on wrongdoing in organisations for her book. As an in-house lawyer, Animah drove harassment awareness initiatives and has spoken about sexual harassment predominantly in the Malaysian media. She is now based in London.