Gfilui

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

If your friend was talking to a male coworker who (presumably) he doesn't find attractive, he would not do these things. 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.

Unfortunately, focusing on so many different factors might only add to your friend's anxiety, 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.

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.

If he finds himself overthinking the act of complimenting the shirt, then it may be that he actually does want to flirt, and isn't sure what to do about it. It is then a good idea to consider doing nothing and letting it go.

However, if compliment the shirt he must, it's best to say "hey, cool shirt," and make that the end of it. If this seems somehow unsatisfying, refer back to the previous paragraph.

To be extra safe, if the shirt is of a somewhat revealing variety, just let it go. Making a compliment about a revealing shirt will almost certainly come across as flirting.

I would not compliment any co-worker on something like clothing unless we were friends outside of work.

At work, I eagerly compliment people on their work: work ethic, quality, personal passion etc..

I think it's too risky these days to compliment a co-worker for non work related things. Besides, what do you get from it?

It seems like there has been confusion and doubt before the compliment has even been delivered. To me this is an instinctive sign to refrain.

Don't.

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 confidant 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.

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 a 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...

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.)

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.

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.

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".