It's weirdly hard to compliment people, at least as a man.

If you haven't warmed them up a bit first, it never feels right to compliment what they wear.

On the other hand, people love hearing that they have a nice playlist or run a cool place. It's something we put a lot of us into, so being complimented about it always hits hard.

Compliments are an acquired skill, but one that's so satisfying to use.

Try non physical complements, eg. I really appreciated the conversation you started on x, I like that we can really go deep and get into the weeds on topics, or even it's cool that you really know who you are.

So that only works for people you know or have interacted in some way. That doesn't apply to strangers.

compliments

I think a lot of that is delivery. In a society like the UK (where I currently live) where there’s a deep and heavy cynicism and sarcasm in the cultural dialog, most people assume you’re taking the piss unless you really can convey you’re not - not that this is a good reason not to complement people if you think it’s warranted.

In NZ the culture is a lot more earnest, so it’s a bit easier.

Agree - I always go for compliments about a choice someone made rather than some quality I perceive them to have. This suggests admiration for something they intended to do or worked on.

"I love that sweater" [that you chose] is a lot friendlier IMO than "you look great in that sweater"

I also try to indicate with my tone and bearing that a response is not expected, a good compliment is a gift (IMO) and gifts are freely given without expectation of payback.

I also like to stick to commentary I feel i actually know anything about, i wear earrings, so often comment about them. I dont wear makeup, so i rarely go there. I think fancy shoes are fun, etc.

> I also try to indicate with my tone and bearing that a response is not expected, a good compliment is a gift (IMO) and gifts are freely given without expectation of payback.

Yes! This so much this!

Questions are a great way to indicate interest without coming off as too forward. Where'd you get that hat? Is that sweater as comfy as it looks?

Instead of compliments, try a more neutral start, like a question.

* Is that the new model of X? They say it's great.

* Where did you find Y? I've been searching for it a long time.

* Do that Z work so well as they say?

I am a guy. Feel free to ask me questions via email on how I do it.

My only actual skill: being fine with awkwardness. It happens 20% of the time

I'm really reluctant to talk to strangers, but when I do... I use triangulation, where you don't talk about yourself (a stranger doesn't care) and you don't talk about them (it makes them uncomfortable), but instead you talk about a 3rd subject that maybe is visible to both of you, like the pretty fall leaves.

Actually, last year, right after I learned about triangulation, I was walking my dogs and stranger mentioned the pretty fall leaves to me. I then started telling him that he was using triangulation and explained what it is. He got uncomfortable and walked away. Derp.

Taking a conversation meta will make a lot of people uncomfortable, yes.

Just don't ask about the weather https://xkcd.com/1324/

This is called small talk, and despite being reviled by many needs, it serves an important social purpose of making people feel comfortable before we talk about things that can get uncomfortable (like each other).

Most people agree that it's silly but needed, which is why when you deconstruct with a random stranger (thereby making it about the two of you and NOT a separate thing), they will feel the need to quickly exit your presence.

I don't think compliments are a good way to interact with strangers. Better is asking for the way to ..., most important thing is to follow your intuition.

I remember the first time I went to Austin from the UK for a work trip. I wore my usual stupid pun t-shirts and the amount of comments/compliments I got walking down the street from strangers was insane to me (at least once a day).

The first few times I probably reacted poorly because it was so unexpected. I thought they were trying to get me to stop so that their friends could go and mug me or something. Took a while to get used too it and say something normal back.

I wouldn't take the negative/lukewarm responses personally, maybe they just don't know how to respond properly due to never experiencing it before.

Haha. American here. I still remember when I moved to Austin from Boston. Even within America Texas is a fairly friendly, outgoing place. At least compared to metro living on the East Coast.

The culture shock was noticeable. In Boston if a stranger walked up to me to say something my feet would already be pointed in the direction in which I intended to walk away from them. Whereas in Austin people are far more friendly, outgoing, and open to impromptu social interactions. I found it a very welcome change.

My theory is that such attitudes are heavily influenced by population density. If you live in a city that is packed full of people you start to guard yourself against the number of daily social interactions you will allow. For many, it’s emotionally draining to constantly acknowledge, say hello to, chat with, or humor every person that you meet. When you commute on the train every morning that becomes quiet time for you, even when you’re in a train car full of other commuters. It’s generally considered rude to chat up people too much. At least don’t be surprised when people want to keep to themselves.

Whereas in Texas and parts of the American midwest there is less need for people to live right on top of one another. Everyone travels alone by car, walking is less common. Meeting strangers in public is then less of an imposition and generally more of a warm-hearted experience.