I am asking this question for a friend. My friend is straight, male, and married to a woman and loyal to his wife. He is a somewhat socially awkward person.

He works in an office of software engineers. The other day, my friend was telling me one of his co-workers (she) was wearing a kimono-style shirt, and he was unsure about giving her a compliment without coming across as flirting.

He ended up asking what material the shirt was made of and commenting that it looked comfortable.

She responded pleasantly and went on to say that she got it from a thrift store and it was one of her favorite shirts. Then they both got back to work.

Both of them have not socialized outside of work. They have socialized in work socials out of the office (movies, picnic, etc), but not extensively.

They see each other daily at work in the office and don't talk much, other than some chit-chat about the weather and how they are in general.

He does not want to make things awkward by potentially coming across as flirting. It wasn't absolutely necessary to make the compliment, he simply wanted to say something nice to a female co-worker, while respecting her.

My friend is naturally quiet, other than making some small talk and talking with co-workers for collaborative tasks and such.

For future reference: How can he approach complimenting her without making it awkward between the two?

  • 19
    Please don’t write answers in comments. It bypasses our quality measures by not having voting (both up and down) available on comments, as well as having other problems detailed on meta. Comments are for clarifying and improving the question; please don’t use them for other purposes.
    – Mithical
    Commented Jul 31, 2018 at 18:42

11 Answers 11


Coming from my experience in receiving compliments from men I didn't know very well, I'd suggest focusing on complimenting the shirt vs complimenting the person wearing the shirt.

For instance, saying something as simple as

"That shirt looks good on you, the color brings out your eyes."

can be taken as 'flirting' by some (especially strangers who don't know each other very well), due to the fact that the compliment is aimed more at the person and not the shirt. I think this often happens because individuals tend to get caught up on hearing the words 'you/your', regardless of what the surrounding context may be. For this reason I'd try to avoid any compliments in which the word 'you/your' is involved (even though there are potentially some exceptions).

However, a statement such as

"That's a cool looking shirt, what kind of material is it made of?"

focuses instead on how the shirt looks without ever mentioning how it appeals/adds to the coworkers appearance or body shape. This runs less of a risk of being misinterpreted by the other party.

Once you establish enough of a rapport with someone, it becomes less awkward/risky to give compliments that do involve their physical appearance. So long as the coworker is more of a casual acquaintance though, I would recommend sticking to compliments focusing on the shirt over compliments with emphasis on the person wearing the shirt.

  • 7
    Maybe mention why your first example is bad and that the girl shouldn't be brought up at all in the compliment. Even "that shirt looks good on you" by itself might be taken creepily as "that shirt fits your body well" or "I like how you look in that shirt." Especially in the workplace, best to leave no room for misinterpretations.
    – scohe001
    Commented Aug 1, 2018 at 21:53
  • 1
    This answer could be improved by adding the perspective about how often women receive unwanted flirting (or worse). Many men are unaware of this and it's a context to any "you look great!" types of statements and why it's important to the significance of the first part of this answer.
    – enderland
    Commented Aug 3, 2018 at 11:29
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    @EdmundReed I disagree. I'm suggesting the least risky ways to give a compliment but still admitting it can be taken as flirting - there are factors that will always be out of your control (such as the person you're complimenting and their social perceptions). If you ask me how to feed a bear in the wild without getting mauled, I'm going to tell you that you can use fish or other raw meats, but that doesn't mean you're completely safe from becoming a snack.
    – Jess K.
    Commented Aug 6, 2018 at 13:23
  • 1
    Another way to think about it, explained to me by several ladies, is that compliments should be directed towards things that the woman can control (ie: cool shirts, awesome hair style, excellent means of destroying the patriarchy) and not so much on things she can't control (figure, physical features, etc) The former seems more genuine and highlights her as an individual. The latter seems more objectifying. Commented Dec 19, 2019 at 15:37

Jess K.'s answer is spot-on, but I wanted to add some additional detail.

The challenge is not only what your friend says but how he says it. Body language, eye contact, tone, cadence, and other things all can create a flirtations subtext, even when your friend is trying to act calm and cool.

When flirting, men tend to lean in, make direct body contact, look directly into the eyes of the other person, shyly smile, raise an eyebrow, play with their clothing, and various other "cues". For what it's worth, here's a list provided by the esteemed reporters on NBC's Today show

Unfortunately, because your friend has social anxiety, focusing on controlling his body language might only add to his tension, for fear he might unconsciously screw up some subtle cue. One trick that might help is to visualize his coworker as male (or perhaps even as his boss) and note how his body automatically shifts to create a different subtext.

If your friend was talking to a male coworker who (presumably) he doesn't find attractive, his body language would not include these typical "flirting" behaviors. He would, for example, maintain a certain distance and a relaxed posture (instead of leaning in), avoid the appearance of wanting physical contact, and keep the tone light and friendly. He wouldn't have a nervous little smile, because he wouldn't be nervous.

As far as verbal openers go, the fact that your friend is married provides an easy way to talk about clothing with any female coworker.

Hey, that's a nice top. Where did you get it? I bet my wife would want something just like that.

Bringing up your spouse is (usually) a clear signal that you are not flirting, and that your interest is in the context of making your spouse happy. While this might not be 100% true (a topic for a separate IPS thread) nevertheless it helps frame the discussion within "appropriate" boundaries.


As a straight married male not interested in flirting and trying to avoid awkwardness, he should avoid complimenting members of the opposite sex on things he noticed for making them look attractive.

In the workplace, try and treat members of the both sexes similarly. Would he often compliment male co-workers on their clothes that he noticed for making them look attractive?

This doesn't mean all comments about clothes are off-limits; e.g., if a male or female coworker came in with a T-shirt with a reference to something you like or is funny, it's fine to start some small talk about their reference. Or if the office is normally casual wear and someone came in wearing a very fancy clothes, it's fine to start a conversation about it.

But if he doesn't frequently compliment male coworkers on their clothes being attractive, it's probably mildly inappropriate to comment on female coworker's clothes for being attractive. This isn't to say she should call HR or his wife if he said a simple compliment about an attractive shirt, but many women feel uncomfortable about strangers or distant acquaintances commenting about their appearance, even obliquely. This is true even when it was a sincere compliment with no ulterior motive, because it isn't possible for her to intuit his precise motive behind the comment.

In summary, in the future he should compliment her for similar reasons that he compliments his male colleagues (examples like "good idea", "thanks for being so helpful", "great work", etc.).


The difference between compliment and inappropriate behaviour is in the way you do it, more than what you do.

You can easily compliment people, by

  • Making clear through your behaviour that this is what you intend (and nothing more), and
  • Anticipating that they may be worried anyway, and so making very clear by your manner, that is all you intend.

What follows is an actual example I had myself, a few days ago. I happened to see a young lady with really nicely done hair, at a train station. I wanted to compliment her (a stranger and young female POC) without triggering concern. My motive was that I felt she might like this, so long as it didn't worry her.

I just said as we waited near each other, "I just wanted to say, your hair looks amazing", I smiled briefly, and then almost immediately, I started to walk about 20 yards up the platform and began reading things on my phone, looking towards the train tracks not at her. I got into a different carriage, and didn't see or speak to her again, or even look for her.

She got the compliment, and also got the message that I truly had no ulterior motive. Because:

  • I didn't try to convert the compliment into a conversation, or use it as a "hook" to engage her any further.
  • I didn't try to stay in her personal space, or near her
  • I didn't try to watch her for any reaction
  • I immediately turned my interest back to normal disinterested passer-by things, like my own phone, and my expected train, nothing about her (as if we had never spoken)
  • I walked away "normally", like anyone walking down a train platform. Not furtively, or guiltily. Just like normal. But not too slowly, and not looking back or anything.
  • I didn't try to pick it up later.
  • I didn't act like I had done anything wrong, or weird, or that I needed to explain anything to her, or carry on talking to apologise, or explain it was safe, or anything. I just shut up and left well alone/walked away, saying nothing more.

I think this last point is really important. It's so tempting to explain, but its actually an extended engagement that is most likely to cause worry (whatever is said or whatever the intention!) than anything else. Trust that skipping it, and skipping any other hint of further interaction, will work better than misguidedly trying to "make sure it's okay". If due to aspies or any other reason, this doesn't make sense, trust it anyway. It's very important.

In an office setting you can do the same, with modifications.

  • say "that looks nice", and nothing else. Say it as a compliment, but keep it bare, don't embellish, don't add more, and make clear what exactly you are complimenting.
  • Then immediately, but without acting guilty or furtive, or rushing, go do something of your own stuff. Some work, or a file that's elsewhere, or a coffee or whatever.
  • Don't explain, expand or apologise, or try to say anything more.

If the colleague wishes, they will say thank you. If they don't, they won't. If they do, you can say, "I didn't want to say more in case it wasn't wanted". Then again shut up, they will comment if they wish, if it was fine. But most people in my experience will be OK with a very brief compliment, as there isn't time to get anxious or worried before it's over - and it's clear the person really didn't mean or want anything more.

In a separate incident yesterday, I got to see the reverse side of this. I was walking down my local high street with an LGBT friend with a new and frankly awesome haircut. A passerby - a complete stranger - walking on the same side towards us, said as they passed, "Love your hair!", and said nothing else and carried on walking without stopping. My friend, who is quite stranger-phobic and anxious socially, and would normally worry, was left smiling by the compliment and the way it was done, and felt good.

In today's society, that's probably the safest way to do it, apart from simply not doing it.... which is always safe.


Firstly, a rule of thumb that I find works for many (heterosexual) males:

  1. Think of a compliment.
  2. Pretend she's a man.

If the compliment suddenly seems homoerotic, 'weird' or doesn't seem like a compliment, don't say it, think of something else.

I.e. things like "you look hot in that shirt", "that shirt compliments your figure" or even "you're looking well trimmed, have you lost weight?" are not good.

Secdonly, praising someone's skill, intellect or taste (in TV/food etc) is usually a much safer bet than commenting on their appearance. Something simple like "good thinking", "excellent idea", "that drawing you've made is nice/skillfully done", "yes, Stargate is so much better than Star Wars - you have excellent taste in scifi".

I've had numerous platonic relationships with females, and as far as I'm aware they never construed any of my comments (e.g. about their artistic ability, about their taste in TV shows etc) as a form of flirting.

(Disclaimer: my view may be skewed by the fact I am not in the habit of regularly complimenting people.)



Complimenting a co-worker on her appearance is just too dangerous in the modern office environment. It can easily be construed, rightly, or wrongly, as a sexual overture, and potentially as sexual harassment.

If his goal is NOT to begin a romantic relationship, then the potential gain is virtually zero, and the potential harm is that he could be having a meeting with HR, black marks on his record, maybe even lawsuits, or losing his job.

Even if this co-worker is pleased to receive the compliment, or he's confident she wouldn't complain about it regardless of how she took it, any third party over-hearing can complain.

It's just not worth it. Don't. If you want to strike up a friendship with a co-worker, talk about work, or sports or hobbies.

RE comment from @avazula: I don't claim to have done a scientific study on this. I'm simply speaking from personal experience and common sense.

I can think of a number of workplace incidents that I have personally witnessed, or that I read about in the news because things went as far as lawsuits.

Just for example, once two co-workers of mine were discussing motorcycles. A man made a comment about enjoying "having that much power between his legs". If you heard the whole conversation, there was nothing sexual about it: he was talking about motorcycles. If he intended some sexual innuendo, it was very subtle, or at least, I didn't see any sexual innuendo. Nevertheless, a woman in the office heard just that snippet of the conversation, thought he was making sexual overtures, reported him to HR, and he got in trouble. He wasn't fired, I don't know exactly how far it went, but he got a stern lecture about making sexual advances in the office.

Example 2: Saw on the news: A man watched an episode of the TV series Seinfeld. The episode included a joke whose punchline hinged on someone remembering a woman's named because it rhymed with "vagina". He thought it was funny and sent an email to a female co-worker telling her the joke. She complained to HR and he was fired. So... it's legal to broadcast this joke over the air to millions of people, but not to tell it to one person. Hmm. I could give many other examples. Anything remotely resembling talk about sex in the office is extremely dangerous to your career.


I think your friend should seriously rethink why he wants to compliment her and whether doing so serves any purpose beneficial to himself or to her. Does he usually compliment coworkers he's not close friends with? Does he often find himself wanting to, for both male and female coworkers, but feel socially awkward about doing so? Or is it a matter of this particular person being "attractive" and him wanting to get the experience of having complimented her (and her reaction to it)?

If he'd like to become someone who feels comfortable complimenting others around him on small things, I think he should put this person out of his mind and start by complimenting people he's not attracted to on things not related to their appearance, or at least not their bodies. It may be spontaneous and friendly to mention you like someone's shirt or their new glasses the first time you see it, but if you hold that thought in for the first few weeks you see it, then bring it up, it sounds really awkward if not outright creepy, like you've been dwelling on them and trying to get up the nerve to say something. It would really be better to focus on complimenting people's ideas, and in ways that aren't just flattery but that actually acknowledge their roles and that you value what they've done - like at a meeting saying "Hey, last time [person] had a nice solution to a similar problem. Would that work here?"

If on the other hand your friend just has a thing about wanting to compliment this particular woman because she's attractive, then essentially he wants to flirt without it looking like flirting, and the right answer is just "stop".


I would suggest, that if your friend is really nervous about paying this person a compliment, it might be best to avoid doing so.

Reason being, his nervousness may be misinterpreted as being due to some kind of romantic interest.

I'm not suggesting he can't ever pay her a compliment, however it's probably best to only do so once he feels more at ease with her.

Saying something like...

Hey, I like your shirt!

Needn't be in any way inappropriate, or flirtatious, but nervousness could unfortunately cause it to be interpreted that way.

I may say something like that to a female colleague, if I knew her very well, and worked with her on a daily basis. With other female colleagues, who I might not have known for very long, I would probably not comment, even if I just genuinely liked her shirt, and had no romantic interest in her.

Office etiquette can be tricky. If in doubt, it's best to just keep conversations very professional. The last thing your friend wants is to make his colleague feel awkward or uncomfortable around him.

His intentions may be perfectly respectful, but it's all in the interpretation.


From my experience, even Jess K's the second question

"That's a cool looking shirt, what kind of material is it made of?"

can be interpreted as flirting (especially when coming from a socially awkward person). If your complement ends in a question, it shows you intention to have a prolonged conversation on a topic outside of your profession with them.

Even the suggestion Andrew mentions

"Hey, that's a nice top. Where did you get it? I bet my wife would want something just like that."

could send mixed signals, and not just because of the opening to talk about non-work things. Someone interested in you could interpret bringing up your wife as defense for a guilty conscious. Moreover, such phrasing could function as a soft 'neg' because it could be interpreted as saying, "If you were my girlfriend I'd buy you that top a gift, but you aren't...". Interpreted together, it could come across as either an intentional (or subconscious) desire to have an affair.

If you really want to just complement her say:

"Oh! I like your shirt!"

then quickly get back to discussing work things...


Maybe it's better to compliment something about a co-worker's work, than what they wear -- or something they did ("it was nice of you to do X" or "you talked well with Y"), rather than what they look like.

I don't know about you but I don't really enjoy people talking about my appearance, at work I might rather they talked about work.

Anyway I think that would come across as less (or as not) flirtatious.

Some people in a comment asked for reasoning:

  • I interpret "flirting" to mean some kind of sex-influenced or sexually-charged communication -- see this answer for example -- if the compliment is something you'd say to a "girl" but not to a "guy", then perhaps you shouldn't if you want to avoid any possible appearance of flirting.
  • I think it's considered healthy (though I won't provide a reference for this assertion) to encourage (perhaps by complimenting a.k.a. giving positive feedback to) people's virtues ... i.e. what they do, their skills, their kindnesses.

    My personal experience is sometimes disliking or feeling nonplussed by people's commenting on my appearance in the workplace ... so the "golden rule" suggests to me that I should refrain from doing that myself, and thus I forward this suggestion to you too.

    Conversely, work-related positive feedback is not just healthy generally but appropriate behaviour in the workplace, even from colleagues and not just from managers ... and therefore not inappropriate (which I think is relevant to the question, because I took "not flirtatious" to mean more broadly "not inappropriate to this in-workplace interpersonal relationship")

  • I understand there is or has been some "sexism" in the workplace, women not being treated as men are treated ... e.g. being treated as (sexual) objects of attractive appearance (i.e. passive decoration), rather than being treated as workers (i.e. active agents) -- hence I think it's polite to compliment someone's work rather than their appearance.

    I also say this because I assume he wants to compliment her somehow -- the question is asking how to do that -- and instead of saying "don't compliment her" I'm replying "compliment her on something other than appearance".

  • Switching focus to the person's behaviour (instead of 'grasping at signs' of physical form) may help the OP steer clear of any flirt-adjacent thinking.
  • I think it's generally (outside the workplace too) polite to compliment someone (intentional) actions rather than their (more genetic) appearance.
  • 2
    Hi there! It's likely that your answer got downvoted because it is a frame-challenge answer and therefore does not answer the initial question, i.e. how to compliment without coming across as flirting. Though (frame-challenging is accepted on this stack)[interpersonal.meta.stackexchange.com/questions/2511/…, we expect people who suggest it to explain why OP should not try to do what they asked for. We asked you to edit to justify why OP shouldn't try to compliment, so now your answer is good. :)
    – avazula
    Commented Aug 7, 2018 at 15:40
  • @avazula Thanks for explaining -- i.e. that any "frame challenge" requires a more explicit explanation than normal. My answer was, "Compliment, yes: but not her shirt." IMO the latter risks being perceived as not only flirtatious but sexist, perhaps even "damning with faint praise" -- compliments (positive feedback) can be (are) good, but she might prefer to be complimented on another (career-related) subject than her shirt -- and, focusing his attention elsewhere (than on her shirt) might alleviate the OP's fears or inhibitions.
    – ChrisW
    Commented Aug 7, 2018 at 16:03
  • I did get what you were saying, and I think you're making a point here. Its just that you were asking why you got downvotes so I thought you'd appreciate to learn more about frame-challenge rules over there :)
    – avazula
    Commented Aug 7, 2018 at 21:19

A man complimenting the appearance of a woman who he is not that friendly with (as seems to be the case here) will always have the risk of being misconstrued as flirting. Since she responded well the first time, there is low risk of his actions being misconstrued if he follows the guidelines above.

What really matters here is what his motivation is for complimenting her - is he only noticing her outfit because she's attractive, or did she stand out because of how stylish her outfit is?

Since she was wearing a "kimono-style shirt", the latter seems like a reasonable explanation. He might have a genuine interest in her top because he hasn't seen anyone else wear something like that before. In that case he might say something like:

"Sorry I don't know much about fashion but your shirt looks really cool, what is the style called?"

to indicate that he's interested in the design of the top, not her wearing it. Obviously he can't do this every day, but if she is notably one of the most stylish people in the office (I'm addressing her specifically because the question is asking about future compliments to her), she is likely aware of how her outfits stand out from the rest. I think it's healthy to encourage men to develop an interest in fashion (male or female) and ability to compliment others' clothing without it always being interpreted as flirting.

Some of the previous answers about not complimenting her because she should be treated just like a man are unreasonably harsh, IMO. Typically men at the office (at least my office) wear very bland outfits, like a t-shirt and jeans or a suit depending on how casual the work environment is. If a man complimented another man at work wearing a gold blazer and ascot I don't think it would come across as homoerotic, but complimenting someone in the same dark gray suit everyone else is wearing would. When there are less differences in clothing, the implication is that the person wearing the clothes is attractive.

Background: I am a twentysomething female software engineer in the Bay Area who is into alternative style, which means I wear things like platform boots and tank tops + cutoff jean shorts to work all the time. I get lots of comments on my appearance from my (predominantly male) coworkers, such as "you always look like you're ready to go to the beach!" or "that's an interesting shirt, where did you get it". Considering that my clothes are more personal style than to look conventionally attractive, I generally believe that they catch people's attention because they are unusual, not because they show off my body.

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