How To Tell a Stranger They're Beautiful

Sure, it sounds easy.  Just head on up and say, “Hey there, angel-eyes, is it legal to look that good?”  Splash on some cologne, show off the guns and show a little chutzpah, right?  Nay!  Guess what?  That’s the road to becoming “That Guy”.  In this context, “That Guy” means “Douchebag”, you Douchebag.  Take your unjustified self-confidence and get the hell off of my blog!  (And shave that pencil-thin chin-outline you call a beard, you look lame.  By the way, that tattoo of barbed wire on your arm isn’t “tough-looking”, it says “I’m a bottom”. )

They gone?  Good.  I hate those a-holes.

Where was I?  Oh yeah.  

It really isn’t that easy.  Especially to those of us that don’t have all that douchebag-level of self-confidence.  Plus, if you do just go for broke and say it, you’re not taking into account a number of issues that need to be addressed.  (Trust me, this crap can get complicated.) Luckily for you, I’ve gone and done most of the over-thinking needed. (Don’t thank me, just doing my vastly underpaid job.)

First important issue:  Motivation.

Why have you elected to do this?  This is a much more important issue than you may think, because it is also contains a hidden danger.  If you’re doing it to “impress”, or “get digits”, than that is the campaign trail to be President-Elect of Douchebag-aria and why the hell are you still reading this, I told you to SCRAM!  Douchebag!

Yes, doing this as a pick-up line is a hidden danger.  Because it’s not supposed to be a pick-up line… it’s supposed to be a compliment.  A simple, sincere compliment.(Emphasis on “Sincere”.) If you’re doing this to get in someone’s good graces as an effort to eventually get them naked (or ask them for money, or a recipe, or whatever)… then it immediately becomes “You’re only saying this because you want something.”  Even if you honestly do believe them to be beautiful, the fact of you trying to take it further suddenly makes it sound like complete bullshit. Something that is merely: A means to an end.

This is not supposed to be a means to an end.  It’s supposed to be an end in itself.  You follow me on this?  Hear what I’m talking about?  I’m saying that this is something to which you will receive no reward.  Not even as a long-term plan.  Your return-on-investment on this is NOTHING.  Zero. Nada. Zilch.  A big bowl of “Nut ‘n Honey”, and I’m not talking about the breakfast cereal.

Sincerity is the name of the game here folks.  Like what Linus looks for in a Pumpkin-Patch, there needs to be “Sincerity as far as the eye can see.”  Without it, you’re on the way to becoming the Douchebag (justified or not… just being seen as a Douchebag isn’t a good thing).  

Sure, maybe you’re not a douchebag, but still consider yourself one of those “I don’t care what others think” kind of people.  “So, if they think I’m a douchebag, so what?” Well, for one, that attitude’s getting dangerously close to actually being a douchebag, so I’d start re-thinking some life choices, if I were you.  (Just sayin’)  Second of all, your target’s perception of the situation… is part of the POINT of this exercise.  Here, you have to care what the other person, a complete stranger, thinks at that moment where you say it.  Otherwise:  Mission fail, even if you think it didn’t.

Okay, so why does it have to be a stranger?  What’s wrong with saying it to a friend, or even just someone you know?  Again, sincerity can be a factor.  A compliment like that, even if meant 100%, can be taken with a, “Oh, they’re only just saying that because they’re my friend.”  Or you could get, “Wait a minute, is this person trying to make a move?  I hope they know I only want to be friends, but now it’s all awkward!”  Now granted, it might work out totally in your favor… and there’s nothing wrong with telling your friends that you think they’re beautiful… I’m just saying:  You’re on your own, but good luck.

Well, my motivation comes down to two things:  One, when reading PostSecret, or browsing around on Tumblr, or elsewhere around the internet where strangers find the freedom to express themselves anonymously… I occasionally see a wish posted that says, “I wish a stranger would tell me I’m beautiful.”  I thought… why a stranger?  Well, if a stranger approaches you to say that they are honestly attracted to you physically, then the “beautiful” part starts out honestly.  But if they’re STILL a stranger afterwards, not asking for anything… then it confirms that the only motivation was a true and honest opinion… that you are in fact, beautiful.  There’s a lovely romance in that wish.  And it’s one that I can have the ability grant to others.  (Even sometimes make that wish for myself… even though I don’t consider myself much of a “romantic”.)

Secondly… there are some people that I think really deserve to hear it.

Second important issue:  Location

You do have to pick your location fairly carefully.  You don’t want to do it in an obvious place.  Doing it in a bar or nightclub… why bother?  First of all, it’s hard to hear (which affects later issues)… and for another thing, people that go there are usually all dolled up to the nines TRYING to look like that.  So if that compliment comes, it still going to have the element of “Oh, they’re just saying that because I’m showing all this skin”.  But wouldn’t that compliment mean a little more if you heard it while wearing jeans and a t-shirt, coming out of the post-office, showing no skin and even wearing minimal make-up?  One location is where people are fishing for those kinds of compliments, and the other is where it’s totally unexpected.  Ironically enough, it’ll be more appreciated in the location where it’s a surprise, believe me.

I’ve done this a few times at my gym.  Which is a risky location, I know.  Because people there are “trying” to look good (in a long-term sense), while maybe not necessarily looking “club/bar-level good” at that moment.  Also, you may still see the individual after the compliment is given.  But with the nature of the gym, you can still remain strangers with just about everyone.  Just as long as you’re careful and selective, so you don’t become seen as another “That Guy”.  (In this case, “That Guy That Tries To Pick Up Chicks At The Gym”.  Too many in too short a time, and that’s who you are.) But on the plus side, you can do a bit more pre-observation on the target, so as to make a slightly more informed choice on whether or not the individual is worthy of receiving said compliment.

Which brings me to the third issue:  Selection.

You have to be selective.  You can’t say it to just every pretty face in the joint, eventually making your way to everyone over a period of time.  I don’t care if you think you’re freaking Rudolph Valentino and say “Every woman is beautiful!”… that doesn’t make you a lothario, that makes you a horndog with low standards.  (And if Rudolph Valentino was really that great, don’t you think the other reindeer would have asked him to join their reindeer games?)  Certainly, there is merit to the statement “Every woman is beautiful”; Every individual woman is going to be considered beautiful to some other individual.  In my first apartment in California, I shared a kitchen with a 400-lb. woman.  She was a sweet soul and all, but not physically attractive to my eyes (especially after seeing her eat 3 packs of Ramen Noodles in one meal).  I hope she found someone that sees her as beautiful… but I’m okay in admitting I’m not one of those guys.

So, even if you’re like me, and believe that Beauty does come in many shapes and sizes, you still have to draw the line somewhere.You’ll still have a decent-sized pool to choose from.  Now, you have to start narrowing it down, to find the one that you believe really deserves to hear it.

Now, from here on the selection process involves making possible assumptions about people based on looks alone.  No, that’s not 100% respectable, I understand.  If a lawyer pointed that out in court, I’d sound like a sexually-harassing a-hole.  In fact, saying it here could be evidence for ME being a douchebag.  That’s a risk I have to run.  But the pool has to be narrowed down somehow; otherwise, again, it means nothing.

Okay, first thing I do is eliminate the “Hot” girls.  I mean the ones that are stereotypically “Hot”.  They subscribe to the media-barrage standards of what “Hot” is.  Look at the way they carry themselves.  You can usually tell by looking at someone if they have the “I’m Hot and I know it” attitude.  I’m not saying look for the ones that have low-self-esteem… just eliminate the ones that have maybe too-high of self-esteem.  They obviously don’t need the boost, and the compliment would probably be wasted on them, anyway.

In the gym, it’s a touch easier to spot them, because every muscled jackhole is trying to flirt with them.  Now, me being an introvert, I’m a bit of a people-watcher, so I occasionally notice things like that as I’m going from exercise to exercise.  I don’t think the Gym is a place for socializing; it’s for getting work done, and getting healthy.  So the flirters tend to stick out.  The meathead guys usually go for the stereotypical “Hot” women, because they think the amount they can bench-press deserves the lady’s attention.  And the gals being flirted with have most likely heard it all before.  For them, they might not even make the differentiation between “Hot” and “Beautiful”, so it all sounds the same to them.  So, it’s probably a wasted effort on our part, and even more a likely chance they’d think “Ugh, what a creep-o.” (Unless I had a six-pack stomach and Calvin Klein-underwear model looks, then they’d probably respond favorably.  Hey, there are shallow women, too.)

So the stereotypical Hot ones… out.  Sorry, that’s the way it goes.

Ideally, what you want, is someone who is beautiful… but maybe isn’t told so very often.  Which is a pretty big category, sadly.  Maybe it’s more accurate to say:  Someone beautiful… who considers themselves “average-looking”, and is okay with that.  Or even that believes “The right person will think I’m beautiful.”  (Acknowledging that not everyone will) Well, even if I’m not the right person… I can see it.  And I think that’s a person worth telling it to.  I think the compliment wouldn’t be lost on someone like that.

Actually pinpointing that kind of person… is a crap shoot, I admit.  But a big part of it probably comes down to what YOU consider to be “Beautiful”, and how that might compare to a friend’s opinion.  If you see someone as beautiful… but think they’re probably the type some friends of yours would say, “Eh, she’s pretty.” Or “She’s alright”.  Right there, it’s obvious that you are seeing them in a higher opinion then someone else… in which case, you’re on the right track.  Got yourself a potential candidate there.

But don’t go jumping the gun!  I see you’re about to jump on over there and make your presence known… hold up! You can’t do it right this second!  Why?  Issue #4, my friend:  Timing!

You swagger over there at this moment, you’re right back to the “Douchebag” issue.  You might as well put on the Douchebag club pin right now!  (Hey, didn’t I kick you out of here earlier?  No?  You sure?  Yeah, right… I’m watching you, Buster!)

Timing is vital on this, I really believe that.  You don’t want to interrupt anything.  If she’s hanging out with friends, forget it.  Even if you did manage to compliment her, the friends will either scoff and make fun of you for trying a “pick-up” in front of them, (cock-blocking even when you weren’t attempting to… “cock”?) or maybe even get jealous and say, “What about me?  Am I Beautiful?”… and you don’t want to be prompted to say it out of obligation, because then it even feels like bullshit, and deep down, they know it’s not as satisfying because you were prompted.  No, you need to catch them when they’re alone.  At the gym… don’t interrupt them in the middle of a set.  That’s just rude.  And besides, you’d rather have their full concentration, not splitting it with “what number rep am I on?”  Full concentration can help with full appreciation.  So, during a workout is very tricky.  Maybe the only time you could get away with it is when they’re wiping down the exercise machine.

But you also don’t want to do it with anyone around.  Even if outsiders don’t care, for the target… if it’s something they might find embarrassing (whether by virtue of “can’t take a compliment” or “someone is making a fuss over me, oh no”), you want to minimize the potential for that happening.  This should be a fairly private moment… no one else’s business.  In the parking lot is a good place, where most other people would be out of earshot, if they’re even around.  (Yet, it’s not so private that she would have to worry about her safety… you want to minimize any potential “threat” factor for her, too.)

But don’t stand and wait for her in the parking lot.  Because this is the element you pretty much should leave up to fate.  IF you find yourself in a comfortable public-yet-non-threatening-private-ish location… IF you find yourself in said location with the target in close proximity… IF the target is not otherwise occupied… and IF there’s no interlopers in the area, then you should be good to go.  But it can be a small window of opportunity, that could be easy to miss.  Go about your business, and if the paths cross with the circumstances in the right place… well, okay.  But if you two are parked on opposite sides of the parking lot… don’t go in her direction until you get in her earshot.  Make the approach just before the actual path split.  Go a little out of your way, but not a lot.  Going too much out of your way… can be creepy.  

Yes, this does mean that it’s possible that opportunity will never arise.  It may happen.  That’s okay.  Let the Grand Imaginary Powers of Coincidence do their thing, and if those Powers are kind… you’ll have your window of opportunity to make your approach.  (Okay, you can help them along a teeny bit, by picking up your pace, or slowing it a little; if it betters the chances of being at the ideal spot at the same time.  Just don’t be obvious about it, and be prepared to abort on the slightest notice, okay?)

Now, we come to The Approach.  The fifth issue.

Don’t go starting with a “Hey Toots.”  Or a “Yo, wait up.”  Forget about “Hey Girl!” And do NOT even think about a “Howyoudoin?”  Don’t go into it with cockiness, or suaveness, or Valentino, or tough-jock attitude.  Frankly, in this instance, for what is actually trying to be achieved…  do not step in with “confidence”.  You go in with confidence when you want something, when you’re pursuing someone with intentions that are, in essence, selfish.  (Which isn’t always a bad thing… but it’s just not the point of this.)  Here, I’m saying go with something else.  Not with the opposite of confidence, but something a bit more towards that side of the spectrum:  Humility.

A simple “Excuse me”.  Not said with a tough attitude, or a wink, or a seductive tone… but rather with the attitude of “You would do me the honor of bequeathing 5 seconds of your attention in my direction.”  Gentleman-like, that’s all.  If they don’t hear, or keep walking… then abort mission.  The moment has passed… no harm, no foul.  Just enjoy the rear view for 2 more seconds (hey, I’m only human), and then keep on your merry way.

Chances are, you will get their attention.  Then it’s the time for the truth.  Just make sure it IS the truth, otherwise, you’ve screwed this up way back at the beginning.

For me, I find myself usually introducing the statement:  “I just wanted to say…”  As I think it would feel too “weirdo” for me just to say cro-magnon-like “Ungh… you boot-ee-fall.”

Now, I also tend to throw in a little extra something… mainly because I’m paranoid, and I honestly want the person to be complimented and not weirded-out.   And despite all precautions, this could still be seen as an unsettling experience.  So, either just before or just after I’ll say “I really hope you don’t feel uncomfortable by this… it’s not a pick-up or anything…”  Though, I’m usually kicking myself afterwards for adding that.  I don’t know… maybe I’m using too much humility in there.

But, now it’s been said… bringing us to the last issue:  Reaction.

This is not only about the Target’s reaction… but yours as well.  For the Target… you really only want them to be gracious.  A simple smile and thank-you… recognition and appreciation.  It’s awesome if they are genuinely moved by your sentiment… but that won’t always happen.  Anything beyond simple “appreciation” is gravy, quite frankly.

But your reaction can also be a factor… remember:  This is not a pick-up.  You are not to ask anything from this person.  But if she does think it’s a pick-up, and rejects you, thenyou have to remain gracious, say, “That’s okay… I just wanted to say that.  Nothing more required.” Then politely excuse yourself.  

This is another reason that you can’t make it a pick-up… because a rejection may come.  But you won’t actually feel rejected, if you’re sincerely NOT doing it as a pick-up.  Because there’s nothing to be rejected… and the compliment still stands.  (It’s not that I’m afraid of rejection… okay, I am, but that’s completely beside the point…)  But if you compliment her, she rejects… and you feel rejected?  What do most douchebags say?

“Stupid bitch, you’re ugly anyways.”


“Dumb whore!  Screw you!”

Yeah, they retaliate with an insult to save their precious egos… and also makes the original compliment completely null and void.  Good work, asshole.  Now do you see why I kicked you out in the first place?  There’s nothing wrong with letting the lady have the last word.  If they truly were worth the effort in the first place, they’ll remember you met rejection with a sense of grace, and did not take back what you said… which means you must have really meant it.  And they’d probably be a little humbled by that… congratulations, you’ve made them a better person!

Even if her reaction is ideal… you still need to excuse yourself quickly, lest the awkward-phase descend, and the sincerity of the gesture disappears.  

I know I said to take out the confidence and come in with humility… but oddly, if you do this way, you actually demonstrate a different kind of confidence.  The confidence of honesty.  Too often, the people who are overly-confident in this world, seem to have no problem lying their ass off, to get what they want.  And those same confident people who say they’re “just being honest” about something, are usually saying something pretty shitty.  As a whole, we’re pretty much trained that when someone says, “Hey, I’m just being honest here…” you know they’re going to say something you’re not going to like.  (That’s actually known as “Liar Liar Honesty”.)   So here… you can actually throw them for a bit of a loop… in a very good way.  Under the insistence of sincere, unadulterated honesty… you can actually make their day.  Which doesn’t happen nearly enough in this world.

I have recently said this to someone.  It’s been a long while since I’ve last done it, and hadn’t even considered it in that time.  (Granted, it’s not something I wake up and say, “I’m going to find someone to compliment today”.  I just try to keep my eyes open and if the occasion occurs… great.  I tend to average once every 9 months or so.)  She goes to my gym, and I started noticing her every now and then when I was on the cardio machines.  Then I realized I was noticing her more and more.  If I was on the stair-climbers in the back of the room, and she jumped on one of the treadmills directly in the next row up… I’d say to myself:  “Cool… I get a nice view today.”  As neutral as I was keeping my attitude, with regards to the people around me at the gym… she seemed to stand out, by not really doing anything at all.  She kept to herself… did her workout and leave.  I don’t think I’ve ever seen her talk to anyone… just does her thing and moves on. 

She has very short, brunette hair… and I don’t really know why, but I have a semi-“thing” for short-haired brunettes.  Now, short hair doesn’t work on every woman… but those it does work on, it looks really good.  And believe me… on this woman, it looks freaking great.  It suits her incredibly well.  She has an angular-face (and I like angular faces… again, not sure why), gorgeous eyes… she looks simply Beautiful.  With a capital B.  And I know I’m going on only looks alone, and maybe it seems a bit shallow (but right now, I don’t care.  Bite me.)… but if you asked me at the time, “Of all the women in this room… which one physically looks like someone you’d want to fall in Love with?”  I’d probably say her.  This is not meant to sound “stalkerish”… just “very admiring of her appearance”.

Now, I don’t know if she’s married or taken (I haven’t seen a ring on her finger, but doesn’t mean it isn’t there… or maybe she takes it off for her workout), I don’t know her personality, her name… heck, I don’t even know if she’s in my age-range for dating.  She could even be Lesbian, who knows?  All I know is her appearance.  And she is absolutely in my definition of Beautiful.

So, I thought about it for a bit… and decided, “If the opportunity comes around… I’ll tell her.”  Now, I don’t always see her there… for one, I don’t always go to the gym at the same time every day.  But when she is there, I usually spot her.  We never crossed paths, but I didn’t try to facilitate that happening.  (Like I said, it needs to be left to the Grand Imaginary Powers of Coincidence.)  Then, I finished up my workout, went to the locker room, walked around the old creepy naked dudes, got my stuff together and headed out.  Walking towards the front door, I pass by the staircase that leads down from the upstairs locker-room (the Women’s one).  I see out of the corner of my eye that someone is coming down it, probably will end up right behind me going out the door into the foyer.  So, once I go through, I pause and hold it open for that next person (a polite habit I’m fine with keeping).  I turn my head and see that it’s her… the Beautiful brunette.  She says, “Thanks” (for the door-holding… and a pretty voice, by the way), and goes ahead through the outer door.  The only other person that was there just went inside as we were coming out… so this looked like the opportunity.

It was raining a little, so she paused briefly as she stepped outside to put up the hood on her jacket…

“Excuse me?”

She turns and looks right at me, looking slightly surprised (understandable)… this is the first actual contact I’ve ever had with this woman.

“I… hope this doesn’t make you feel at all uncomfortable, but… I just wanted to say… I… think you’re incredibly beautiful.”

(I don’t know why I put so many pauses in there… not entirely intentional.  It’s not like I can “abort mission” anymore at that point.  I’m committed, gotta go through with it.)

She smiles… (a really nice smile, too) and says, “Oh, that’s so sweet!”

“Don’t worry, this isn’t meant to be a pick-up or anything… I just… wanted to say that.”

She says, “Thank you so much… that’s really sweet.  Thank you.”

“You’re very welcome.  You have a good evening. “

“Thank you, you too!”

And we walk off to our separate cars.  I didn’t look to see what she was driving (that seems like a stalkerish detail to try and discover), just got into my car and headed off like normal.  (I was also being rained on, and I didn’t have the rain jacket with the hood.  Eh, it was worth getting wet.)

I’ve seen her at the gym a few times since, and we even passed by each other a few times.  Met with eye contact, and a smile.

It appears that the mission was a complete success.  She seemed genuinely appreciative of the compliment, as I hoped she would… and the aftermath is nice, too.  Doesn’t seem insulted or weirded out by me (as she’s at least acknowledging my existence)… and maybe exchanging a smile with me can be a nice reminder to her that yes, someone does find her sincerely Beautiful.  That’s a role I’m happy to play, and wouldn’t want to jeopardize.  And just maybe… I granted her a wish.

However, if SHE were to strike up a conversation with ME… then I’d have to say all bets are off.  (I just first have to make sure she’s not married/taken/lesbian/etc…)

But that’s how I tell a stranger she’s Beautiful.

Now, go kick a douchebag for me.