Have you ever asked anyone if you're pretty?

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Yes

I am neurotic about "prettiness" I was an exceptionally homely child...now I am a "decent" looking adult......I will get compliments from strangers that I am pretty...I have a lot of You Tube vids....people seem to think I am "cute" though I was flamed a lot for being fat before I lost 30lbs which I am gradually gaining back....If I ask my boyfriend if I "look ok"...he will aloofly hint that I "seem alright"...Best not to ask....

No.
There are too many variables.
For one thing, what's pretty to one person may not be pretty to another.
Also, the person I'm asking may lie, either to make me feel better or to make me feel worse.
Even if I got an honest answer, how would I know it was an honest answer?

It sounds so pathetic, too.
When I think of the question, I see an image of a girl with crooked red lipstick. Mascera runs down her face as she cries, "Am I pretty? Am I?"

Nope and I wouldn't. But I've been told that several times.

Yes.

I have asked someone if I was pretty, but I'm not so sure they were being truthful. They said yes, but I'm not sure.

AM I PRETTY?

....."I don't know...ARE you?"

YES....but NOT Pretty Enough!! !

Ive never asked any1, its a very awkward question, When I actually think about it, I find it really weird if someone tells me Im pretty or beautiful. Like if someone tells me that and there another girl, a relative, an older person(outside the demographic that might be attracted to me), I think there just telling me that to raise my self-confidence. If a guy tells me that, I think hes delusional or despirete. I know Im not ugly. I also feel prettiness is judged based on the way a person portrays themselves. If you smile a lot, act girly, sweet, etc: people are more likely to tell you your pretty, beautiful, gorgeous: well at least ur friends will. If you dont act like a girly airhead, people are less likely to tell u ur pretty.

If someone says I'm pretty and it catches me off guard, I might reply with "really?" Without being prompted, I'll ask if I look okay before going out and that's about it. >.>

i've never specifically asked anyone their opinion on my looks. but i have sometimes gotten some positive feedback either in real life or when i post pic, which is nice to hear. my self-esteem doesn't rely only on outside observations though. it matters more to me when someone takes one of my comments to heart or if they appreciate something intangible about me, an ultimately it's my own opinion about myself that matters most.