Can you give a woman a compliment on her appearance? Not any more, it seems

There was a time when I felt comfortable giving a compliment to a woman on the street. I would say something like, “You look very smart. I think your dress is lovely.” It was entirely innocent; there was no ulterior motive, and it wasn’t a puerile attempt at a chat-up line.

But if I were to give a similar compliment to a woman now, chances are it’d be seen as a bit creepy.

I had to give up trying to read statement T-shirts after it became clear that trying to read the message ran the risk of offending the wearer. But I would argue, and plea, that if you don’t like being looked at by strangers on the street, why wear a T-shirt with words on it and invite unwanted stares?

You might wonder why I once felt it was significant for a woman to know what I was thinking. Or, more precisely, what were my motivations in giving a compliment to begin with if not trying to pick someone up? Well, for the simple fact that receiving a compliment can be lovely.

Trust me, if I am paid a compliment on my appearance – something exceedingly rare these days – I feel both amazed and wondering if I am the subject of a Specsavers commercial. Once, when I was walking in Kings Domain, I was stopped by a much younger woman who asked if she could take a photograph of me on the basis that I looked really comfortable in my clothes. When I pointed out that was likely because I was in my weekend baggies, she replied, “Don’t worry, I’ll leave your head off.” So, was this a compliment? Maybe, maybe not.

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There have been occasions in the past when I have asked a woman if she would mind if I complimented her choice of colours in her outfit, the cut of her coat or her smart suit. The few times I have done this, I have been greeted with thanks and even a smile. Clearly, asking first seems to be the new etiquette for these kinds of exchanges.

Grey hair and being well past the first flush of youth is no excuse to make someone uncomfortable, of course, but it seems the line between compliment and feeble attempt at picking up someone has been completely blurred. The question I am left with is whether women and men actually like receiving compliments on their appearance to begin with. We have no problem complimenting a person on a job well done or an achievement, so it seems the problem lies in the personal.

I accept that a compliment, depending on the setting and tone, could be seen as a kind of harassment. If a male employer compliments a young female staff member on her short skirt, that would not be appropriate. Saying “nice frock” to a co-worker, however, should not be considered a threat. Perhaps it is different when the compliment is paid to somebody of the same gender as there is, for the most part, less risk of ambiguity. Or perhaps age plays a role, with men and women of the same social era feeling more like equals.