Conversation Chillers: Awkward Compliments

It happened almost 15 years ago, but the memory is etched with crystal clarity.

It was the first week of sophomore year of high school, and the first rehearsal for the fall musical.  I bounded in straight from marching band practice in 90-degree heat, wearing jean shorts, unusual for my grunge/goth phase.

I spotted a new acquaintance – Mitch (totally not his real name), a guy I’d met only a few days before in my Algebra II class, lurking on the edge of the stage.  He liked the same bands I did, which was incredibly important in high school, and I thought he might have the makings of a real friend.  I sat down next to him and smiled.

He looked at me and said, eyes burning into mine, “Whoa.  Your legs are incredibly muscular.”

Now, to fill in a little extra context: I am 99.9% sure this was intended as a compliment.  I didn’t know it at the time, but Mitch was always just kind of weird and intense (picture the neighbor kid from American Beauty and you’re pretty spot-on).  Later, he got a girlfriend and made equally unusual observations about her.  Also, we stayed friendly for years.

But back to 15-year-old me: I had never given the slightest thought to the state of my legs, and now I was terribly self-conscious about them.  Were muscles a good thing, or was marching band turning me into one of those lady body-builders?  When I wore shorts, were guys reminded of thoroughbred horses?  Was he telling me I looked hot, or was he trying to tell me I should keep my robo-legs under wraps?  Or was he just really into anatomy?

You might think this stands out because it’s only strange compliment I’ve received.  On the contrary, I think it stands out because it was one of the first of many.  Now, I do think I’m at least somewhat conventionally attractive, but if I only had what others have said to go on, I’d reach an entirely different conclusion.

It makes me wonder if compliments are something of a dying art.  I once watched a celebrity, a man in his 50′s, at a signing.  He managed to come up with something nice about every single person he talked to that was both true and said with sincerity.  And the people he complimented positively glowed, because, let’s face it, we don’t hear stuff like that often.

But if you can’t say something nice…

On the other hand, a backhanded or just plain awkward compliment can leave its intended recipient pondering that gem for days, or, well, years.  So following is a smattering of things have actually been said, and suggestions for alternatives that hopefully won’t keep people up at night.

You look like Alanis Morissette, because of your long, messy hair.  Yep, this is another gem from my school days.  Two problems here:  First, comparing someone to a celebrity is tricky, especially if said celebrity has something unconventional about them to begin with.  You might think of it as a compliment, but attractiveness is subjective, and the person you’re complimenting will have their own opinions.  Tell a girl she looks like Sarah Jessica Parker and you could get any response under the sun.

Second, messy hair is not attractive, even if it’s true.  If you really want to tell someone they remind you of someone else, maybe just tell them who it is and leave it at that, without trying to reason out why.  Presumably you’re saying all this off the cuff, and it’s best not to get tangled up in the details.  Your brain might say “lithe and graceful” but your mouth says “skinny and bony.”  Your brain might say “intelligent and aristocratic” but your mouth says “you know, that nose.”

You’re really good at dressing for your figure.  Yes, we’re not all supermodels, or, if male, Brad Pitt in Fight Club.  Yes, we try to de-emphasize our flaws and play up our strengths.  However, no one wants to be reminded that we’re just trying to make the best of what we have.  Furthermore, if I wanted to get all “What are you really saying?” about this one I’d wonder if they meant that the package looks better in the wrapping paper, if you know what I’m saying.

A safe, simple alternative to this one would be something along the lines of “That’s a pretty outfit” or “You look really nice today.”  Yes, it might be a little generic, but that doesn’t mean it has to be any less sincere.  On the subject of specifics…

That sweater makes you look like a Barbie doll (or anything else you wouldn’t say to your Grandma).  All right, so you appreciate her curves.  And sex is definitely a part of romance.  However, there’s a time and a place for such comments, and most of the time it’s not, say, on the first date, or before the date when you’re just hitting on someone you’ve just met.  Plus, when you start focusing on individual body parts it can make your date feel… objectified?  Disembodied?  That doesn’t mean you can’t be flirtatious, especially if the chemistry is palpable, but say it’s a nice sweater and leave the rest to her imagination.  Specifics are a more advanced level.

You look better without makeup.  I get what you’re trying to say here, that getting all gussied up is unnecessary, that you think they’re attractive regardless.  The problem is, when you say you prefer someone under one circumstance, they’re going to wonder if that means they look unattractive the rest of the time.  Now, if you’re genuinely trying to be helpful, like you’ve noticed one style of clothing is particularly flattering, there is a time and a place for it, and it’s typically in a more comfortable, established relationship (and even then it’s safer to say something like, “You look extra awesome when you wear blank” and thus imply that they’re at least regularly awesome the rest of the time).  When you barely know the person?  Keep it to yourself.

And if you’re just dying to point out that you prefer the au naturel look, try this one: “You don’t need to wear makeup.”  It’s a tiny difference, but a significant one, implying they’re just as attractive with or without it.

You have really pretty skin.  There’s actually nothing wrong with this on the surface, though it is a bit unusual; it’s being included to underscore the importance of context.  For instance, you just might not want to say this one shortly after you’ve watched Silence of the Lambs and go on, ask me how I know.

So yep, these are just a few of the gems that have stuck with me over the years – and I promise I’m actually not a person who over-analyzes every last sentence for the real meaning.  By the way, it’s experience like this that makes me so annoyed when I read about the pick-up artist technique of “negging” – essentially insulting the target.  The idea is that an attractive woman is so used to having attention and praise lavished on her that disinterest or insults will get her attention.

Now, ignoring for the moment that the idea that a woman needs to be “taken down a few pegs” is stomach-churning, I’ve never known anyone who was rolling in compliments and who didn’t have insecurity lurking somewhere.  And the really pretty girls – I’ve known some knockouts – are often the ones who’ve had the weirdest, pickiest things pointed out to them, by spiteful people of both genders.

So don’t let this dissuade you from complimenting people altogether; I really think the world needs more compliments.  My point is that you don’t have to go all advanced or specific to brighten someone’s day or even to be memorable.  Something as simple as “You have a nice smile” or “You look pretty today” or even “I like your shoes” is easy to say and hard to mess up.  And if it’s not in your nature to say these things or you’re worried about getting nervous under pressure, start practicing now!  Your barista or your checkout person won’t mind a stray compliment, I assure you.

What about you?  Have you gotten a “compliment” that left you wondering, or have you put your foot in your mouth yourself?  I’d love to hear your own tales!