When is it appropriate?

[QuidProQuo77]

As a mid-50s dude I avoid complimenting young women if they look nice because it would seem kind of creepy.

I was in a store the other day and saw a woman (guessing in her late 60s) with long white hair and a pretty face that left me breathless.

I was very tempted to remark about how good she looked, but held off. If I was single I would have gone for it, but I wasn't trying to pick her up.

Should I have said something?

 

[Que]

General, non-bodypart specific, complements are always appropriate. Age is never a factor if one can pull it off with good eye contact and avoid a leer. Compliments delivered whilst looking at body parts are generally creepy.

Pro-tip: treasing compliments will get you a more responsive smile because they contain an element of plausible deniability. "You have an awfully pretty face...for a girl." Some sort of backhanded compliment relieves the social pressure of it looking like a come on or that it needs be returned.

 

[Aquagal]

General, non-bodypart specific, complements are always appropriate. Age is never a factor if one can pull it off with good eye contact and avoid a leer. Compliments delivered whilst looking at body parts are generally creepy.

Pro-tip: treasing compliments will get you a more responsive smile because they contain an element of plausible deniability. "You have an awfully pretty face...for a girl." Some sort of backhanded compliment relieves the social pressure of it looking like a come on or that it needs be returned.

I don't agree. I've never liked back handed compliments, and think they are rude. Plus, and why would you call a 60 yr old woman " a girl"?

 

[Aquagal]

As a mid-50s dude I avoid complimenting young women if they look nice because it would seem kind of creepy.

I was in a store the other day and saw a woman (guessing in her late 60s) with long white hair and a pretty face that left me breathless.

I was very tempted to remark about how good she looked, but held off. If I was single I would have gone for it, but I wasn't trying to pick her up.

Should I have said something?

Also, your bio says 49, but your post says mid 50's?

Whoopsie!

 

[Que]

I don't agree. I've never liked back handed compliments, and think they are rude. Plus, and why would you call a 60 yr old woman " a girl"?

Because I'm teasing in a "girls are icky" sort of way that harks back to grade school. The older she is the more likely I would joke and that way. Results vary, however. Evidently, I would not be picking you up whilst betting the odds that a back-handed compliment would ne more effective.

I'm assuming that we're talking a complete stranger here not someone that you at least on a nodding, friendly basis with. If its someone well known to you and you're just complimenting them on how they look that particular day or especially someone you're dating, an open sincere simple compliment would be the way to go.

 

[Que]

Also, your bio says 49, but your post says mid 50's?

Whoopsie!

..and his user ID suggests 38,

I would assume that 1977 was a good year for him....

Now I'm seeing him as the Matthew McConaughey character from "Dazed and Confused"having graduated in 1977 still hanging around..

 

[Lyricalli]

A simple "you look lovely today" is probably going to be taken well as long as it doesn't come with gawking, kissy noises, and prefaced with "hey mama".

 

[Fala]

A simple "you look lovely today" is probably going to be taken well as long as it doesn't come with gawking, kissy noises, and prefaced with "hey mama".

I'm totally with you here, Lyric! ...and done with a smile. If she actually stops and looks at *him* and smiles back....

a "would you like to go next door for a coffee"?

Now THAT'S how it's done.

Thanks Lyric! Now ya done it...*she* is married; husband finds them together at the coffee shop next door, nuzzling each other in the corner booth and shoots them both.

Ok, I'm watching way too many crime shows! heh.

Seriously tho, Lyricalli, your suggestion is excellent!

 

[Lyricalli]

Seriously tho, Lyricalli, your suggestion is excellent!

Why, thank you!

 

[Saint Peter]

Maybe the guy is a barista and could make her a nice cup of joe in the back of his windowless delivery van.

 

[Fala]

Maybe the guy is a barista and could make her a nice cup of joe in the back of his windowless delivery van.

...and what is that large, empty cedar box for in the back of the van?

If the cafe wasn't within a very short walking distance, she won't go. period.

 

[Saint Peter]

...and what is that large, empty cedar box for in the back of the van?

If the cafe wasn't within a very short walking distance, she won't go. period.

My van is parked in the alley.

Oh. Yeah.

 

[Fala]

My van is parked in the alley.

Oh. Yeah.

Is it white?

 

[butters]

As a mid-50s dude I avoid complimenting young women if they look nice because it would seem kind of creepy.

I was in a store the other day and saw a woman (guessing in her late 60s) with long white hair and a pretty face that left me breathless.

I was very tempted to remark about how good she looked, but held off. If I was single I would have gone for it, but I wasn't trying to pick her up.

Should I have said something?

could have simply said 'wow, you're hair's amazing!' offered a big grin and left it at that. not creepy, unlike some of the other things i've read here. i'm 56 and it would have given me a smile without feeling you were trying anything.

 

[Disgustipated]

Q-Bert giving advice on how not to be a creepy douche bag is hilarious.

 

[Saint Peter]

Is it white?

Two tone.

Rust and primer.

 

[Fala]

Two tone.

Rust and primer.

I've got pepper spray and a little sister...and I'm not afraid to use her.

 

[Saint Peter]

I've got pepper spray and a little sister...and I'm not afraid to use her.

Both of those are in the cedar box.

 

[Fala]

Both of those are in the cedar box.

No, my pepper spray is in my pocket. I reach for it and accidentally press the button, triggering it off in my pants....

 

[Fala]

Petey has fled the scene...and left me standing in the alley with pepper spray going off in my pants.

How INappropriate!

 

[Lancecastor]

Windy day yesterday; while walking to my car, a cutie in a sundress was putting bags in the trunk of her Civic.

A fotuitous gust lifted her dress as i walked by. No panties.

So, being the gentleman i am, i pulled her dress back down over her ass and offered to take her panty shopping.

She told me she didnt need panties, but could use a drink.

 

[Fala]

Windy day yesterday; while walking to my car, a cutie in a sundress was putting bags in the trunk of her Civic.

A fotuitous gust lifted her dress as i walked by. No panties.

So, being the gentleman i am, i pulled her dress back down over her ass and offered to take her panty shopping.

She told me she didnt need panties, but could use a drink.

Bwahahahaah! so. punchline?

 

[Wings]

"I love your look" is one of the least douchey things I've ever heard. It wasn't threatening, it wasn't leering, it wasn't uncomfortable. Backhanded compliments are the absolute worst. You want the lovely lady to feel good about herself, not shitty. And they are ONLY ever appropriate if you have an established relationship already.

 

[Disgustipated]

I feel most backhanded compliments are not really meant to be. Meaning, it may be the compliment-er is just a shy person incapable of projecting his thoughts as meant to be to the lady. More of a fumbling of words, if you will.

 

[Wings]

I feel most backhanded compliments are not really meant to be. Meaning, it may be the compliment-er is just a shy person incapable of projecting his thoughts as meant to be to the lady. More of a fumbling of words, if you will.

You have a pretty face for a fat girl is not a compliment. You have a pretty face for your age isn't either.

I do understand that some people are uncomfortable giving compliments but to deliberately add a backhand to it is gross.