The title pretty much says it all, I know there are cases where giving compliments to strangers makes them uncomfortable (for example, catcalling), but as I understand it there is a separate set of compliments one can give that are much more likely to be taken positively.

A rough heuristic I've come up with so far is to only compliment decisions; that is, if you call someone beautiful you're objectifying them, but if you call their jacket beautiful you signify that you appreciate their choice in clothing, which is much more likely to be taken positively. But I'm not sure this is a robust enough rule to be used safely.

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    complimenting anyone or the opposite sex? I feel gender may be important here if the latter, correct me if i'm wrong. Aug 30, 2017 at 21:32
  • @BradleyWilson I would prefer answers about anyone, that address the special issues that come up when dealing with other sexes/genders (assuming there are such special cases). Aug 30, 2017 at 21:36
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    I think the answer will depend a lot on who they are and the reason you're complimenting them. Are you looking to ingratiate yourself to make a sale? Do you think the stranger looks sad and need to be cheered up? Are you currently trying to escape arrest by complimenting your way out of it? Aug 30, 2017 at 21:42
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    Please, please don't call catcalls - "compliments". They are not.
    – Catija
    Aug 30, 2017 at 21:45
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    If you have to ask such questions I think no compliment to strangers is save. This is about intuition and not analytical decision making
    – Raditz_35
    Aug 30, 2017 at 21:48

9 Answers 9


Context Matters

Your heuristic analysis is somewhat correct, but there are many driving factors here and the current answers don't even begin to cover (except @Catija's) them. It's much safer to compliment someone on what they're wearing than to compliment them on their looks. I wouldn't compliment someone on their physical appearance unless I know them or have been speaking to them for a while already. Anyway, let's break this down:

Driving factors to consider

  • Age
    A compliment will be better received from someone in their 20s to another person in their 20s, rather than someone in their 40s complimenting someone in their 20s. (Gender hasn't been taking into account here)
  • Time of day
    The later in the day, the less well received the compliment might be. I certainly wouldn't approach someone in the street at around 10 pm, but rather in daylight preferably. (Location hasn't been taken into account).
  • Are they with people?
    Would you approach someone on their own walking down the street or would you compliment someone with their friends? The latter would be better received (how you compliment i.e. complimenting clothes or looks hasn't been taken into account).

  • Location
    Are you approaching these people in a bustling urban area or in a rural part of town with barely anyone around?

  • Gender
    This is the biggest factor. It certainly depends on your gender, a man approaching a man, may be better received than a man approaching a woman and vice versa. (no other factors, have been taken into account)

  • Your intentions
    What are your intentions? to instigate conversation? or to simply make their day a little better? The latter would be better received (how you compliment i.e. complimenting clothes or looks hasn't been taken into account).

  • Race
    Be wary of what you compliment about the other person. I wouldn't approach a gentleman or woman and compliment them on their dreadlocks, or something to do with their cultural heritage. Choose your words carefully.

Complimenting their clothing

You can take a couple of approaches with this:

Is there a general rule for when/how to compliment a stranger?

  1. A drive by compliment

    Personally, this is the approach you should take overall, keep the compliment on clothing, not their physical appearance. You don't know the strangers or their previous experience with other strangers. This can be easily done and easily unheard, too. But it shouldn't matter.

    What to do

    • Ensure they are walking towards you, they need to somewhat be in your line of sight.
    • Smile before the compliment and you could say:

      You're rocking that jacket! Keep it up

    • Keep walking!

    What not to do

    • Cross the street to compliment them (you approaching them can startle anyone)
    • Make any form of contact with them, don't tap them on the shoulder or follow behind. They don't know the compliment is coming and you lose nothing complimenting them.
    • Stare at them until you walk past, a simple smile and compliment will suffice. They won't always hear it, but that is life.
  2. A direct compliment which it'll instigate conversation

    What to do

    • Ensure they are walking towards you, they need to somewhat be in your line of sight or not rushing around, i.e. on their way to work.
    • Smile before the compliment and you could say:

      Pardon me? Can I just say I love your jacket? Where did you get it from?

    • Gauge reaction and follow through on conversation if they react well

    What not to do

    • Don't overstay your welcome. You're still a stranger.
    • Stop them in their tracks.
    • Same rules as a drive-by compliment.


I have chosen a street compliment mainly for this approach, I have also taken into consideration both genders (be wary of male to female compliments. women go through enough as it is), if they respond negatively just walk away. Approach people in public spaces in the daylight for the best-received compliment. Most of this should be common sense. But those statistics I've just cited, say otherwise. It can make someone's day but it can also ruin someones. Be careful but also, be nice. We know you mean well, but a stranger doesn't.

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    This is a good answer, and it also affirm's the asker's belief that one should compliment decisions over non-decisions. The important part to remember, I think, is that people enjoy being complimented for things they can change, or have changed to become/acquire. Clothing is a great example of this. Appearance, age, race, gender and so on cannot be changed (at least not trivially) and so aren't worth complimenting. Compliments can be considered constructive criticism of a sort, and if one can't fix something, why criticize them on it? Aug 31, 2017 at 14:56

First and foremost.

Catcalls are not compliments.

Catcalls are the attempt by one person to draw the attention of the other person to them for their own benefit. Here's a Buzzfeed article that discusses it.

Catcalls are directives — Turn around! Come talk to me! Let me see that smile!— which assume at their most basic level an ownership of the woman being catcalled. These aren't innocuous or playful requests; they are symptoms of entitlement, and messages that women don't deserve control over their own bodies.

By catcalling, harassers insert themselves into the personal space of the harassed: during her commute, her daily jog, her walk to brunch. This puts unwilling women on the defensive on a daily basis, where ignoring the comments isn't seen as an absence of a reaction but instead a transgression, or justification for more verbal assaults.

If you want the attention of another person and you do not consider how they feel, don't do it, especially if you're male and they're female and you don't know them.

Yes, there is a (possibly sizable) group of women who like this - consider it an ego boost... but you are more likely to find that your catcall causes them to be uncomfortable - and why risk it?

And here's a Daily Beast article:

Activist group Stop Street Harassment commissioned a national US study of 2,000 participants. The study's findings were disturbing. "The survey found that 65 percent of all women had experienced street harassment. Among all women, 23 percent had been sexually touched, 20 percent had been followed, and 9 percent had been forced to do something sexual.” And we're not even talking about the horribly harassed public life forced on many in the LGBTQ community.

Men need to ask themselves some questions before speaking, like:

  1. Why am I telling a woman what I think about her appearance?
  2. Is it an appropriate place to do so?
  3. Is there some kind of rapport that makes it okay to convey this without seeming like a threat?

Women have made their voices heard and, if you care about other people, you’ll take steps to actually make spaces safer—not contribute to environments that make it worse.

You can have the best intentions but still contribute to an environment that makes women feel unsafe. I, and many fellow men, know this because women say so—they write it, they lecture on it, they write books about it. There’s no excuse for men to be ignorant about what women experience. To disregard that for the sake of instant gratification from women’s attention seems morally negligent. To dismiss it as just “boys being boys” only adds more fuel to the fires where animalistic natures are given fresh life, burning away any notions of being a person or an adult.

So, when is it OK to compliment someone?

As a woman, I find it much easier to accept (or at least entertain) compliments from other women (regardless of whether I know them or not) or from men who I know.

It's very rare that I personally feel comfortable getting complimented by a man but it has happened and usually it's because they've done something like what's in your example and the tone it's spoken in has to convey a level of open honesty that doesn't feel like the person is attempting to get something from me.

Additionally, once the compliment is shared, don't require anything further from them. Make it brief and quick and walk away. You complimenting them is not an opportunity to get their phone number. The problem with catcalls is that, positive or negative, they request/require a response from the target. A compliment doesn't require anything.

I wanted to let you know that you look amazing today. Have a great day! [exit stage right]

Alternately, it helps if it's more of a fact-finding compliment than a pure one:

  • I really love that jacket, I think my girlfriend/mom/sister would like it, could you tell me where you got it?

These two points sound contradictory but they serve different purposes, so it's different.

If I were having a conversation that turned into a compliment. A ten-minute chat about the book I'm reading on the bus would make me more able to accept a "you have great taste in books" compliment or even a "You look so happy when talking about this book that you love so much"...

If you really feel like you need to compliment someone, think about it first. Consider the three points from the Daily Beast article I quoted. Be empathetic and consider things from the receiver's side. And, if you get a negative response, apologize, don't get defensive. You're the one who started the interaction. They don't have to accept your compliment.

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    you look amazing today : I would cut today because 1. It might be the 1st or only time you meet this person (so it's not possible to compare to other days, and even if, that leads to point #2) 2. what about the previous days then? (does that mean I usually don't look good, but just today it's ok?
    – OldPadawan
    Aug 31, 2017 at 9:11
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    @OldPadawan It gave me the impression that the speaker was kind of a stalker... But maybe it's my imagination.
    – Sarkouille
    Aug 31, 2017 at 13:16
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    A catcall or saying "you look amazing" are both going to be weird when directed to a stranger. But to my wife from me in private, they are both compliments. Aug 31, 2017 at 15:26
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    @Catja, while I appreciate everything you wrote, this is still a general question. That the OP used the catcall as an example was probably without much thought. They don't mention the gender in either the title or anywhere else in the question. Maybe they have edited the question after you wrote your answer. Right now, as the question stands, the OP himself calls catcalling something negative. So, I think it would be OK if you change the weight of your answer giving to the catcalling issue do be in proportion to it just being an (explicitely negative) example of the OP...
    – AnoE
    Aug 31, 2017 at 16:47
  • I don't think using buzzfeed as a reference is a wise decision.
    – Hawker65
    Jun 22, 2018 at 13:07

I would say that the time to compliment someone is when they do something that is compliment worthy. Basically, you want to compliment someone for a specific thing, not just to compliment them as a person.

I wouldn't compliment someone, particularly a stranger for something trivial. (You have a bit more leeway with people you know better.)

On the other hand, if you just saw a stranger save someone's life, a compliment from you is certainly in order. Speaking of which, "remoteness" (lack thereof, actually) is also a factor. It's more appropriate to compliment someone for something you actually saw than if you had, say, read about it in the newspapers a few days later.


A lot has been covered but I didn't see anything covering what I call "discount" compliments. These are easy to spot once you understand what I am saying.

"You look great for just having a baby"

"You are in such amazing shape for your age"

"You are really quite good for a novice"

All of those compliments can be given without then adding at the end that the second part. When you add the second part, you then discount the sincerity of the first part because it essentially says something more like,

"You don't actually look great, but, since you just had a baby and if I take that into account, then you do"

"If you were young, I'd say you were out of shape, but at your age, I think you are doing great."

"You aren't good at this, but since you are just starting, you seem to have potential."

The ones relating to age actually bother me the most because they are so common. People want to tell me my grandmother looks great for her age often and for many years now. The fact is, she generally looks great, period. She looks vibrant, healthy, well put together (it's something she places importance on), and her age is just that. It is implied then that people look automatically less great with age, period. I just think that is a very unhealthy and weird stance to take. I also know I am not alone in this thinking. I have heard many women complain about the change over from actual compliments to "for your age" compliments. No one wants that part tacked on, so it's much nicer to leave it off, and since compliments are supposed to be about making the other person feel good by sharing a nice observation you made about them, it's best then to ensure what you said doesn't feel like a back handed insult.

I do want to add this is not the same as when someone says she doesn't look her age. She has never looked her age. That is a legitimate observation. I also do not think that is a compliment necessarily though because it's just true. She is nearing 100 and she has always seemed to manage to look about 15 years younger than she is. She also has enjoyed great health and she has much more mobility than you would expect out of someone her age. It does bother me less when people comment "for her age" now, as now she has outlived most people on life expectancy. This has been something people have said all my life though because she has always been a stunningly beautiful lady, so I have always heard comments on how my grandmother "looks". That is fine with me, but I have never enjoyed the "for her age" piece, as I too find her gorgeous, but we can leave it at that. Had she wished for fame she could have given Sophia Lauren a real competition.


About two years ago, I was struggling with the same thing. I tried to understand human communication like mathematics. I wanted to know the rules of how to have a conversation, how to talk to strangers, and how to talk to a teacher.

I searched the internet far and wide, watching lectures and instructional videos. These resources helped little as I could not perfectly emulate them which made me seem even more awkward.

The thing wrong with this picture is that there are simply no rules in communication. Life is not mathematics, reality, in fact, runs contrary to mathematics. Mathematics is a perfect world created by humans which has all these clear rules and formulas. Unfortunately, this universe of perfection is the exact opposite of life.

My point: Although you can make general rules (heuristics) to better understand complimenting people, like mathematics attempts to explain the natural world, they prove fallacious.

From my experience: Try to act natural and genuine when complimenting. You cannot fake honesty, so compliment people if you really like something about them.

You can compliment them about interesting things they are wearing like a foreign watch, a football jersey. In a professional setting, you can compliment someone about a job they helped you out with or a presentation that you found intriguing.

People will truly appreciate your genuine response. Using complimenting as a means to be accepted by people is doomed to fail. In case you do appreciate something about a person, do not go overboard unless you are very close.

You are right, complimenting someone about their body is going to make them feel very insecure and "cornered," even if it is genuine.


My personal opinion is it's most likely to be well received when used as an icebreaker in a situation where an enduring conversation is possible (the environment permits it), practical (the changing relationship between the people permits it) and welcome (the recipient permits it).

Outside of this, more care would be needed to ensure the purpose of paying it was understood and it was appropriate/welcome to the transaction/interaction taking place. ("Welcome" would largely be judged by the body language the recipient is displaying)

If no interaction is currently taking place (you're not currently talking), or would reasonably arise if one/both parties didn't deviate from their current behaviour/trajectory (you're not going to be close enough to the other person to attract their attention without altering your current position/heading), or the context is such that there's no follow on set of events that you and the recipient will share (you're not both standing in the same line for the same bus/concert/pizza), consider reconsidering

  • I agree, but with the caveat that the complimenter should be prepared to exit stage right if the recipient shows any discomfort. I would feel really weird and unsettled if someone walked up to me, said "I love your shoes!" and then kept walking. But at the same time, I wouldn't want someone to give a compliment to trap me in a conversation that I'm not interested in.
    – Em C
    Aug 31, 2017 at 12:58
  • That's what I was meaning by the latter; in the street, and if I don't want to know where you got them I'd either say "cool shoes; very different" (i.e. a statement that is relatively devoid of my emotion toward them - I don't 'love' them, if that makes sense) or maybe something like "I think my wife would love a pair of shoes like those, can you remember where you got them?" - again neutralising my own emotion toward them, and letting you take away a compliment in the sense of "someone appreciates the effort I put into my look" if you wanted to..
    – Caius Jard
    Aug 31, 2017 at 16:53
  • There's also some element of snap-judgement on how well the interaction would be received; if you're in a hurry, don't make eye contact or any other similar set of body language statements that indicate you're not ready/willing to respond then the opportunity is set aside; that's the "context is such that there's no follow on set of events" (a response)... I'd expand my answer, but I'd essentially be re-stating some of the longer answers here, so I'll probably leave mine as a "TL;DR" :)
    – Caius Jard
    Aug 31, 2017 at 16:56

What I wrote here applies only if you want to compliment someone so much it's like burning you. The best/safest thing to do when meeting a stranger is to leave him/her alone.

What I do when I want to compliment another woman, is to ask first if it's ok for her if I compliment her trousers/hair/style/etc. When I do so, I talk directly to her, especially because I know better than I wish how uncomfortable it is to be yelled across the street that someone wants to fck your arse (or that you have gorgeous titts, or whatever gross stuff some creeps yell). Since I'm myself a woman, I won't come across as possibly dangerous as quickly as a man, so I have an advantage here...

Thr strategy to compliment only decisions seems great to me if you feel unsure but really have to make a compliment.

* since this kind of comments are also catcalling, can I ask you, please, to stop refering to catcalls as "compliments"?


I like to call out to random strangers in the street and compliment them... IF:

  • it's non-sexual, not any kind of a come-on or flirt, so essentially avoid complimenting clothing that's revealing or tight, etc,
  • I don't want or expect a response from them, other than to make 'em smile,
  • it's something they did through choice (in your original question, and a good point),
  • they aren't obviously focused on something else,
  • the thing I noticed about them is far outside social norms, such as hair colorful enough to catch the eye of everyone on the street, showed that etc.

A compliment in this context is a reward for bravery - a reward for shaking off social norms and kicking ass while doing it!

There is no need, no call, no point, no useful outcome, to complimenting a stranger for being normal. "Nice hat" for a regular hat? No point.

For a hat that you noticed a mile off? Hell yeah! For jeans with Thomas the Tank Engine patches all over them? Definitely!


The simplest rule is: don't.

Even if you have no ulterior motive, the receiver of the compliment cannot know that, and will often defensively assume that you do.

Given this, consider the motivation for offering the compliment: even if you're genuinely just wanting to make someone feel good, the risk of making them feel objectified, stalked or harassed should overrule your generous impulse.

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