I want to ask the girl I like to prom and we are going out to eat and ice skating for her birthday. I figured it would be a good time to ask her because we will be alone. I bought a heart necklace with diamonds and I was going to put some sort of prom message in the box. I was going to put this in my car’s glove box with a rose and a birthday card in there as well. As we were driving to the restaurant I was going to ask her to open the glove box and get me something out. Is this a good proposal?
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Welcome to the SDMB, jlange.
The About This Message Board forum is for questions about the message board itself. Since this is more of an advice and opinion question, it belongs in our In My Humble Opinion forum.
Moving thread from About This Message Board to In My Humble Opinion.
If she says no you’re going to have an awkward drive and a very awkward meal. A diamond necklace (?) is also a bit romantic but prom practices vary by area and I don’t know where you’re from.
Yeah, that’ll work. Chicks like the sparklers.
I think it’s a great ruse for a marriage proposal, if you swap the diamond necklace for an engagement ring.
I have noticed a trend in the past few years of young men going to elaborate lengths and spending a lot of money to ask someone to prom. I don’t really understand it.
OP, I concur that your plan seems like too much. Going to the prom together seems to me like a smaller thing than going out together (== forming a semi-permanent couple). And the diamond-necklace-and-rose-in-glove-box plan would be a bit too much even for that, IMO.
Is the birthday thing a date, in your view? In her view?
If yes: If you’ve managed to ask her out on a date, it should be natural to ask her about the prom. Verbally, or maybe in writing if you really think it’s better. But maybe do it at the end of the evening.
If no: If you want to go to the prom with her, just ask her. If you’re too shy, get a common friend to ask her. Again, at the end of the evening, or on some other day.
It’s possible she has other plans or is not interested, and as The Joker and The Thief says, your evening (her birthday !!) would be awkward.
I do hope that she is interested, and wish you the best of luck. 
(Gay man in his forties here. My opinions are based on human nature, not on experience with girls or necklaces in the 21st century. Take this with a grain of salt.)
Even back when we were dating, my Wife would have forcefully twisted my apricots if I spent to much money on jewelry. A diamond necklace is too much. The rose, not too much.
I predict this will end badly but we’ll never hear about it.
End badly? Why bother joining a new messageboard and soliciting the relationship opinions of complete strangers if there is a chance of it ending badly?
Dude… don’t go too overboard. A corsage or some sort of flowers is customary, and so is a nice dinner, but anything beyond that, and you’re getting into creepy territory, unless you’ve been dating this girl for quite a while already. Just play it cool and don’t go overboard… if anything under-do it a little bit and be confident.
Beyond that, it’s prom. Either you’re at the end of your senior year, in which case you might not see these people very often again, or it’s the end of your junior year, in which case anything stupid you do, or anything you botch will be fodder for teasing all of next year.
Better to just ask her to prom, take her to dinner and the dance, and see what happens. Play it cool though- you can’t really lose. If she decides that you suck because you didn’t spend thousands of dollars on something as ultimately stupid as prom, then you’re better off without her. If she decides that you’re someone worth getting to know, then so much the better for you. And if it goes fine, but a larger relationship isn’t in the cards, then you didn’t commit too hard, nor spend too much money.
It’s a risky idea for the aforementioned reasons, but I think you should do it anyway.
Why assume the worst will happen? She’s spending her birthday on a date with you, so thinking she will say yes to prom is not a stretch. We’ve never met the girl and you have, so whether she will think this is the sweetest and most romantic thing ever or that you are overdoing it is something you can answer better than we can.
You could avoid the risk of an awkward evening after her turning you down by saving this for the end of the evening, but maybe then you’d have a bad evening anyway because you were nervously awaiting the moment. Romantic gestures can be risky, but lives are not at stake here. I say go for it.
I think there’s an important shift in the last few years that people are unaware of–elaborate prom invitations are now kind of a “thing”, and this has to be understood in that context.
To the OP, my advice would be to make sure that she’s going to say yes in advance–ask her bff (or get your bff to ask her bff, because that’s the way these things are done). If she’s hoping/expecting you to ask her, then the plan is fine.
This is assuming the necklace is fairly inexpensive.
I can’t wait to read this story in Failed Romantic Gestures on Deadspin in a few years.
At least jlange is asking her in person. I read about one girl who found a “promposal” on her car’'s windshield in the school’s parking lot from her best guy friend. She was thrilled, and ran back inside the school to accept.
“That was your car? I thought it was Jessica’s!”
Well, so I learned that “promposal” is a thing (although still not accepted by the SMDB spellchecker apparently), as opposed to just asking the person to the prom which had worked fairly well during the 20th century.
No, now it has to be overly complicated as suits these 21st century futuristic times (and, as that wikiHow entry shows, requires Anime-style illustrations).
Personally, I would want to separate these things. Here’s your birthday present. Here’s your prom invitation. Admittedly, I am an accountant and I like to deal with things one at a time by default… but the more things you try to say at once, the more likely it is to get confusing.
As for flashy promposals: Even the term promposal makes me throw up in my mouth a little. Kids these days…
Look, whatever you do, never count on a thing to express your feelings for someone. Diamonds and roses and cards are appreciated by most girls, but human nature doesn’t change. What she really wants to know is how you feel about her. And what you really want to do is communicate your feelings without looking like some creepy, obsessive stalker guy who might only be in lust with an imaginary, blow-up-doll version of her.
That does it. I’m officially giving up my career as a romance advice columnist for straight teens.
You could take up a new career designing better web sites. That page needs a shout-out on the nearby thread about badly designed web sites. At least on my (admittedly old version) Firefox browser, that site behaves very … strangely. I can’t scroll up and down with the keyboard arrow keys, only with the mouse. How do you even write a web site that acts that way?
I am not going to discourage you, as we don’t know the background. I have known many high school sweethearts that are still married and happy. I truly hope your sweetie feels the same way.
**Don’t press it if she and you are just dating and she doesn’t know that kind of thing is coming suddenly one night. **
If you truly love one another, just take it one step at a time until you KNOW you won’t have to ask a bunch of strangers on an message board in the middle of the internet.
Please clue us in however - as we seem to be a bunch of salacious advice givers. Most of us have Been There Done That. 
I think it’s very thoughtful and adorable. Please come back, and let us know how it went. Young love is so cute.