Keep it secret, keep it safe
February 27, 2014 2:50 PM   Subscribe

I have been asked by my roommate's boyfriend to covertly find her ring size for an engagement ring. He suggested digging through her stuff until I find a ring to use with an online ring sizing guide. I'm uncertain whether the surprise factor is a bigger deal than the invasion of privacy.

I live with a roommate. She has been talking about marriage and looking at rings with her long-distance boyfriend. He called and asked that I try to figure out her ring size by finding any rings of hers in her room while she's not home. Obviously he wants to preserve an element of surprise even though they've been talking about this. It's a little ahead of schedule from what he's told me so she might still be surprised.

Even though my roommate and I are close friends, I feel like she still might find it a bit of an invasion of privacy if I just root through her room until I find a ring (I'm male if it matters). Additionally, I won't even know if any rings I find will be for the correct finger. Would it make the invasion better or worse if I had a female friend help me?

If you were my roommate, would you rather have me go through your stuff and be surprised by the proposal or would you rather have me ask you for your size and pretend to the boyfriend that it was all secret? Any other options I'm not considering? Maybe guess at her size and tell a white lie to the boyfriend, and then explain the situation to my roommate after the proposal?

I read this previous question ( which seems to indicate this is futile anyway, but I don't think I should tell a casual friend/acquaintance how to propose.
posted by Durin's Bane to Human Relations (57 answers total)
Noooooooo way is it OK to go through her stuff without her permission. Your instincts are correct.

Politely decline his request.

He can dig through her jewelry himself the next time he stays over!
posted by nacho fries at 2:54 PM on February 27, 2014 [17 favorites]

He should ask her for the ring size, there's no reason for you to be involved.

You know your roommate better than us, would she be delighted or angry that you went through her stuff? I'm betting she'd feel a bit awkward. Why risk it? Encourage him to ask her and stay out of it.
posted by Brandon Blatcher at 2:55 PM on February 27, 2014

How about you just let the boyfriend in when roommate is not there, and have him root about? That seems moderately less sketchy to me, and lets you help out and be a "good guy" etc.

But yes, trying to size a ring without an actual finger is difficult.
posted by Admiral Haddock at 2:55 PM on February 27, 2014 [4 favorites]

Best answer: Privacy issues aside, this is a mostly futile quest: Unless you know that she wears rings on her left ring finger... odds are she doesn't have any rings that fit that finger anyway. Most people don't wear rings on that finger because it so means wedding ring. So I think that even if it were 100% fine and dandy to go in there, you couldn't possibly succeed.
posted by brainmouse at 2:55 PM on February 27, 2014 [26 favorites]

Best answer: It makes a difference if you are friends with this roommate.
If you aren't friends, stay out. Ask one of her female friends to do this for the bf, or just tell him you don't feel right looking through her things.

If you guys are actual not-just-roommate friends, then I'd give it a quick shot. You don't have to go through ALL her stuff, you just have to do a little rummaging in the likely places. Does she have a jewelry box? Some area where she keeps little things? Look in those.
If you don't find something in the obvious places in under 5 minutes, you're done. "Sorry bf, I couldn't find anything. Maybe ask her close friend [Betsy]?"
posted by rmless at 2:55 PM on February 27, 2014 [3 favorites]

Male type person here... if I was you, I would tell the boyfriend that I respectfully decline. You are in doubt. I would not go though another person's property if it was not clear that it would be acceptable to them. It's a respect thing.
Another way of looking at it is what's the best that could happen, and what is the worst. The worst scenario, which would be creeping out your roommate, outweighs the positive of making proposal moment a little more romantic, at least in my mind.
posted by elf27 at 2:56 PM on February 27, 2014

Invasions of privacy are not romantic.

Jewelry stores commonly resize rings after the proposal. I think I've read that they advise that size 8 is an optimal guess, and easiest to resize up or down.

Also, previously.
posted by jessicapierce at 2:56 PM on February 27, 2014 [6 favorites]

You know your roommate/close friend (that second part is more important than the first) better than any of us.

Is she private, or does she keep her door open? Did you ever want to borrow something and she replied "it's in my room, just take it" or is she the type from whom you ask permission before even walking into her room when she's in there?

The few people (possibly exactly one person) I know who would be cool with this, I can be 100%, without-a-doubt sure they would be cool with this. If you're not 100% without-a-doubt sure, play it safe and respectfully decline.
posted by griphus at 2:59 PM on February 27, 2014 [1 favorite]

Response by poster: Left this out: there is no time for the boyfriend or someone else to do this because he's proposing when she visits him next week.
posted by Durin's Bane at 2:59 PM on February 27, 2014

Also: Maybe guess at her size and tell a white lie to the boyfriend, and then explain the situation to my roommate after the proposal?

Absolutely don't do that. That's less of a "white lie" and more of a "wholly unnecessary, easily found out about and potentially very expensive lie."
posted by griphus at 3:03 PM on February 27, 2014 [4 favorites]

Best answer: Unless she has a ring that she wears every day on her ring finger, and takes it off and leaves it sitting by your shared sink at night, this whole enterprise is doomed. Any ring you might find would be incredibly unlikely to be the right size, like no better than just guessing somewhere near average. And digging through someone else's stuff is creepy, especially when there is so little chance of it yielding any useful information. Definitely decline.
posted by vytae at 3:04 PM on February 27, 2014 [2 favorites]

Do not do this. Even aside from the privacy concerns, which are completely dead on, my ring fingers vary by an entire size, and many people don't wear rings on those fingers anyway-- plus, the way someone wants an engagement ring to fit is very different than the way they might want their other rings to fit. Resizing, unless it's done through a chain, takes all of an hour. You can get temporary sizers from a jeweler or even from Target in less time.

size 8 is an optimal guess

Okay, if she does look like she has relatively small fingers, he should not follow this advice-- an 8 could only be resized down to a 6 or so. He should talk to the jeweler who has the ring about the best-guess size.
posted by jetlagaddict at 3:05 PM on February 27, 2014 [2 favorites]

have her parents bought her jewelry, like a class ring or a college ring? maybe he can ask them. he can just tell them he's buying her a ring she liked or something.
posted by koroshiya at 3:06 PM on February 27, 2014 [1 favorite]

No need for this. Any reputable jeweler will let him exchange the ring he's got for one that fits if that becomes necessary.
posted by valkyryn at 3:07 PM on February 27, 2014 [2 favorites]

Best answer: Does she have a jewelry box? Or somewhere she keeps all her jewelry, so you don't have to go hunting through her nightstand or random drawers for it? If that's the case, it would not even cross my mind to assume this would be inappropriate! If I had no idea where she kept rings and knew I'd need to spend an hour looking, if the boyfriend asked me to look in her diary or notebooks--those things are inappropriate without a doubt. But if my roommate, a close friend not a friend-by-default-because-we-live-together type friend went into my room and looked through my jewelry box for a good reason, I'd feel completely comfortable when I found out about it later. Really, it boils down to how well you know her, and how concerned she is about privacy. That said, others' concerns about correct sizing are a really good reason to demur. Remember, rings can be resized relatively inexpensively.
posted by tapir-whorf at 3:08 PM on February 27, 2014 [2 favorites]

"Roommate, I'm looking at this cool ring on Etsy, do you have one I can try on and compare to the sizer so I can tell if it'll fit?"

Possibly weird if you're not the sort of guy who wears rings.

(PS, actually be looking at a ring on etsy when you do this.)
posted by Eyebrows McGee at 3:09 PM on February 27, 2014 [31 favorites]

I think people saying that you know your friend better than we do are right, and if you think about it, you know more than just her privacy preferences. You say she talks about marriage a lot - is she the kind of person who will be thrilled with this kind of surprise proposal? If you think she will be truly thrilled, chances are she will forgive this, especially if her bf goes on and on how he begged you to help Just so it would be perfect, etc. Surreptiously check if she is wearing rings next time you see her. If you happen to notice she's got one on the ring finger, then and only then I think it's worth it to peek in when she's gone and check for a jewelry box or something. Don't dig, if you can't find anything you can't find anything.

This is based entirely on my experiences with my friends, who totally would not think twice about my having done this if sparkly ring is the outcome. YMMV
posted by theweasel at 3:11 PM on February 27, 2014

Would it make the invasion better or worse if I had a female friend help me?

Much worse. I mean, it's an invasion if you do it, but at least she knows you.

If you were my roommate, would you rather have me go through your stuff and be surprised by the proposal or would you rather have me ask you for your size and pretend to the boyfriend that it was all secret?

I'd rather you ask me outright and tell me to keep it a secret. But I do not enjoy surprises and am not romantic.

Any other options I'm not considering? Maybe guess at her size and tell a white lie to the boyfriend, and then explain the situation to my roommate after the proposal?

Eh, for the reasons mentioned above I would not do this either.

I think you should either politely decline or tell the roommate what's up.
posted by schroedingersgirl at 3:11 PM on February 27, 2014 [1 favorite]

You could probably do it if she's got an obvious jewelry box out in the open, or leaves a ring out on a dresser or table. Don't rummage around in her closet or other storage trying to find a ring.
posted by BabeTheBlueOX at 3:13 PM on February 27, 2014 [1 favorite]

Best answer: This completely depends on your relationship with your roommate. Currently, I live with a roommate I've been living with for years, and it would be completely fine if I did this. There would be no problem at all. However, as you can see from other posters, above, this is not universal.

Some questions for perspective on the roommate relationship:

- does she close or lock her door when she isn't home (none of my roommates even close their doors.)

- would you borrow her car without prior discussion?

- would you feel like you could let a friend stay in her room when she wasn't there?

These are all things that are ok in some established roommate relationships and not in others. If the answer to all of these is yes, then that indicates a type of closely enmeshed friend-type roommate relationship where you could dig for jewelry. If the answer to all of these is no, I would consider not digging. (There is also the intermediate - look for exposed rings and obvious jewelry boxes, but don't dig.)
posted by mercredi at 3:19 PM on February 27, 2014 [1 favorite]

Take her to the mall (or most big box stores that have a jewelry section). Stop at the ring counter and ask them to measure your ring size for aforementioned etsy ring your mom/dad/dog wants to buy you.

When you're done, exclaim, "Wow, that seems really a weird size. Hey roommate- could you measure yours to compare?"

posted by haplesschild at 3:22 PM on February 27, 2014 [7 favorites]

Even if you decided to do this for him, it would likely be meaningless. A majority of single ladies do not wear rings ever on the traditional "wedding" finger (left ring finger for most, right ring finger for Orthodox Rite Christians or some Europeans), and ring size can vary widely among fingers on the same woman. My right hand is my dominant hand, and the "ring finger" on my right side is actually a larger size than the ring finger on the left. If you dug through my belonging for my (seldom worn) rings, you wouldn't find a single one that was a good fit for a wedding set--he'd probably come closer just by trying to find a (discreet) friend, sister, aunt, etc. who seemed to have a similarly sized finger.
(Also, my rings are passed-down family items or inexpensive "dress up" jewelry that don't fit well anyway, since I don't wear them often enough to resize them.)
posted by blue suede stockings at 3:26 PM on February 27, 2014 [2 favorites]

she really needs to get sized herself. adjustable rings from claires, class rings, and engagement type rings will all fit differently and likes others say, chances are it's not a finger she has a ring for. a surprise is sweet, but you rooting through her stuff won't actually help him. he should be able to describe her generally to his jeweler/show a picture of her and get something that'll be easy to size up or down as needed.
posted by nadawi at 3:32 PM on February 27, 2014

oh - and we bought our wedding rings online from jewelers who exclusively work online and they suggested not using an online sizer - to actually go to a jewelery store (preferably more than one) and get sized. it takes 30 seconds but it makes all the difference in the world.
posted by nadawi at 3:33 PM on February 27, 2014

Yeah unless she has a ring she regularly wears on her ring finger and you know she keeps all her jewelry in a box on her dresser, this is a fool's errand.

Also, I have a bunch of rings sitting in my jewelry box that I never wear. Why? Because none of them fit me and I need to get them resized. Seriously even on the off chance you find a ring, chances are it still won't be right.

Just tell him you thought it through and realized the plan was never going to work and chances are you'd have to tear her room apart to find anything, which really isn't cool.
posted by whoaali at 3:51 PM on February 27, 2014 [1 favorite]

Depending on their personalities, he could propose using an adjustable ring - something fun/cute maybe with a hilariously large "diamond" then get her real ring together at a jeweler... Or if it wouldn't be too outrageously weird, you could go into Claire's (or some other costume jewelry store) and try on rings to be funny. Easier to do if you were female, I think...

But honestly, I think you should tell him the idea of going through her stuff won't work - single women rarely wear rings on their left ring finger, and my left ring finger is a different size from any of the fingers I do wear rings on (I'm a righty, so my right-hand fingers are a bit larger, meaning that rings I wear on my middle & index fingers would also be too large, and pinky rings far too small).
posted by pammeke at 3:57 PM on February 27, 2014

Why don't you tell her that you're ordering a ring online and can she help you work out the size? The while youre doing it suggest that she finds out her ring size too, you know... for just in case.
posted by Youremyworld at 3:57 PM on February 27, 2014

Here is an alternative- this actually happened to me - but it will only work if you are reasonably close to her and she wears at least one ring on a regular basis. In my situation, my friend (who had been been given the task of discovering my ring size) commented on how lovely the ring I wore was, and wondered if she could try it on... Just for fun.. To see how it looked on her. After all, it was not a style she had thought of wearing before. She tried it on a few fingers, until she found one that it fit, squealed in delight, and handed it back with a grin. Not too long afterward, I received a ring that did not need to be sized.

Your roommate might be suspicious of your behavior since it may not be an expected request from you. I did not feel this way as I often wear unusual rings which people often comment upon. However if she is excited about a possible proposal I am sure she would play along, as apparently this is not an unusual way of determining ring size.

I do not think it is a good idea to go through her belongings.
posted by partly squamous and partly rugose at 3:58 PM on February 27, 2014 [3 favorites]

Take a picture of her hand so he can show it to a jeweler?
posted by 3491again at 4:06 PM on February 27, 2014

Suggest he do some kind of candy ring and bring your roommate to the store so it can be sized properly. If I were your roommate, I would want that. I would hate for a roommate to go through my stuff.

You might be able to find out what she likes -- it's probably okay to white lie about how a high school friend/second cousin/etc got engaged and was given (or gave) a ring already chosen, but you'd be too scared to do it and want to pick it out together (or vice versa). This will be especially effective if you don't really know the boyfriend. But there might not be time for this, and if she did want to be surprised by a ring, then you'd be even shorter of time.
posted by jeather at 4:16 PM on February 27, 2014

Another way to do this is to get the boyfriend to buy the loose gemstone and propose with that - this way he still gets to be romantic and present her with something but they get to shop for the setting together, so she gets the exact ring she wants (unless they've had that specific conversation, he may not know) and they can get the ring to fit right first time as it's custom made, and probably cheaper than buying from a store, to boot. Plus no invasion of privacy, win-win!
posted by Jubey at 4:22 PM on February 27, 2014

The points above are all good.

But one more suggestion.

If you're ok at lying - try to get her to tell you her ring size in a roundabout way. Maybe you tell her that your friend Bill is about to propose and wants to get a normal size ring for his girlfriend Ellie so it's close enough to be resized - and ask her what a normal size is, like what she wears? (This works best if she actually knows that you have a couple friend with these names.) Or tell her you want to get a birthstone ring for your mom, etc. Or if you don't think you're going to be able to pull it off, you could ask one of your female friends to do something similar. While it might be a bit suspicious, it's still less obvious than her boyfriend asking her. And it'd get you the information you need without the invasion of privacy. (People are correct that different ring fingers can be different sizes, but it should be close enough in size that the ring could be re-sized).
posted by leitmotif at 4:38 PM on February 27, 2014 [2 favorites]

Personally, I don't have to be absolutely surprised and I really value my privacy, so if you were to be even less oblique than some of the other suggestions - "you guys are looking at rings? can I see? ooh does that one come in your size?" or something - would not spoil the event as much the thought of your rooting around in my stuff, most likely in vain.
posted by sm1tten at 5:00 PM on February 27, 2014

Maybe you could come up with some bullshit excuse for measuring her finger. Something like, "I got into an argument with so-and-so, because he said a woman's ring finger and her big toe are always exactly the same when you measure them around. That sounds like total BS to me. Can you measure your toe for me? Now let's do your finger... See, I TOLD him it was BS!"

That's not great, but maybe you can think of something better. I don't think going through her stuff is a great idea, unless she has some pretty obvious jewelry stash in her room.
posted by Ursula Hitler at 5:16 PM on February 27, 2014 [7 favorites]

"Hey roomie, what's your ring size?"
"Why do you ask?"
"I can't tell you and we never had this conversation."
"Ok. Size 8"

"I was just reading online that the average ring size for a lady is an 8. Are you an 8?"
"Why yes I am!"

Here is what happened with a few of my friends. They wanted to surprise with the actual proposal, but not with the type of ring. So, when it became apparent they were moving toward engagement, the couple went window shopping for types of cuts and ring styles. They also got the ring size. So, a few months later when the actual proposal came, they were able to both surprise them with the timing and have the appropriate ring. You can still do that despite the long distance and limited time. "Honey, I am searching the internet for the style of ring we have talked about. It just occurred to me I will need a size one day. What size are you?" If they have already looked at rings together, this should arouse no more suspicion than she already has. She is probably thinking every time she sees him that this could be the time.
posted by JohnnyGunn at 5:43 PM on February 27, 2014 [5 favorites]

He should get a ring he knows will be too large and have it resized later on. It's very cheap to do and should take no more than a day.

Seriously, everything else is just asking for trouble and stress.
posted by Narrative Priorities at 6:00 PM on February 27, 2014

Whatever you do, don't do something that lets her know what he has planned, even if it's just hinting at it. At best you ruin the surprise he has planned. At worst you cause the end of their relationship (happened to a friend of mine).
posted by NotMyselfRightNow at 6:12 PM on February 27, 2014

1. No, no do not go through her stuff, no no no, ugh.

2. 8 not at all average. 8 is big. I have average fingers and I'm a 6.

3. Resizing is so easy, there is no reason to do this, and even if you did, what people said above about engagement rings fitting differently is true. Just call her bf back and say "hey, you know, I just don't feel right going through her stuff. Resizing is easy so there's no problem, your jeweler can recommend a size that can easily go up or down a couple. Congrats and good luck!"
posted by fingersandtoes at 6:21 PM on February 27, 2014 [3 favorites]

If they have already been looking at rings and talking about marriage, it sounds like there is no suprise to ruin. Tell the boyfriend this makes you uncomfortable (and would be fruitless anyway, as many have pointed out above, since she likely doesn't own any rings that fit her ring finger). I don't see how asking about ring size would tip his hand anymore than looking at rings together! My fiance and I did something similar (looked at rings together, went to a jewelry store to figure out my ring size, which I had no idea about -- how many people know that off the top of their head??), but the timing/details of the proposal were a surprise, which was nice.
posted by rainbowbrite at 6:31 PM on February 27, 2014

2. 8 not at all average. 8 is big. I have average fingers and I'm a 6.
Yeah, I have short stubby fat fingers and I wear a 6.5 or something. But he wants to get it on the big size if he's guessing. You can wear a big ring until you get it sized. A too small ring that won't go on for the showing off the next day will be sadder.
posted by artychoke at 6:35 PM on February 27, 2014

Best answer: Just adding to the chorus of don't do this. She might find it privacy-invasive, and you shouldn't risk that for something that could damage your relationship and has nothing to do with you. Finding a random ring won't work anyway for all the reasons given above. And trying to be tricksy risks spoiling a surprise that's not yours to spoil.

Just tell the boyfriend you think this is a cute idea, but it won't work. I actually think it's a dumb idea and he's kind of a wiener for asking you, but that's neither here nor there :-)
posted by Susan PG at 7:37 PM on February 27, 2014

Adding to the chorus:

a) Don't do it. The privacy invasion is too much.

b) You can't casually bring up any conversation about rings with a person who has wedding rings on the brain. Doing so will make her think you are up to something (which would of course be true in this case).
posted by ktkt at 8:26 PM on February 27, 2014 [2 favorites]

There's got to be a better way. Say you're getting a ring for a friend and her hands seems like roughly the same size as your roommate's. Ask your roommate her ring size to compare. The end.

If she wears rings on her other hand's ring finger regularly and she has a jewelry box where she keeps her rings, I don't think lifting the flap and checking the rings is that big of a deal. But rummaging through her stuff would be weird and I'd decline that.
posted by AppleTurnover at 10:34 PM on February 27, 2014 [1 favorite]

Just a note that some rings can't be resized due to the material - e.g. tungsten carbide (too hard, doesn't bend), or wood. So it may be that he wants to get the size right first time. If that's the case, I imagine most places that sell rings like that would accept an exchange for a smaller size after the proposal. Worth checking in advance though.
posted by EndsOfInvention at 1:49 AM on February 28, 2014

I'm going to go ahead and guess that anyone cool enough to brush off your snooping would also be cool enough to handle a straight forward question from you. I'd just ask. The moment of proposal shouldn't be any less magical for her. She won't know exactly when it's coming, only that it is.

I would suggest to the bf that he just get a ring and go back later to have it sized. Not that big a deal. It happens all the time.
posted by Violet Femme at 4:19 AM on February 28, 2014

Please don't go through her things.

As a single lady, I was as likely to wear rings on my wedding ring finger as any other. Most of my rings are antiques and can only be worn with sizers or with an additional ring, a plain band, as a keeper. Measuring one of my rings would tell you nothing.

I like the idea of starting a ring size conversation with a ruse. She'll see through
it, most likely, but will play along if she and BF have been talking about this. If you both play coy during the ring size convo she'll be able to enjoy anticipating her surprise and also be technically surprised.

He might also consider buying a giant garish costume ring as a placeholder so that they can pick out a ring together.
posted by Lesser Shrew at 5:36 AM on February 28, 2014

I think it depends on your relationship to your roomie. Maybe I'm more laid back than the other commenters, but I wouldn't have a problem with any of my past roommates doing this, but most of my past roommates and I borrowed clothes, books, etc. You know your relationship with your roommate better than anyone here.

Adding to the "this if futile" pile, when I got sized for my wedding/engagement rings, they were MUCH smaller than any ring I had worn before. I never had any "fine" jewelry before, and apparently you don't want those suckers going anywhere. Very different from picking a ring that feels comfortable from a $15 case at the mall.

My husband did manage to sneak away a ring of mine, and the jeweler said, no you need a ring 1.5 sizes smaller, and the jeweler was right! Mind you, this was the guy that was going to make the ring, not a sales guy. So hopefully the prospective-fiancee is trusting a reputable jeweler with good return policies, because even if you do this, there is no guarantee that this will be the right size for that particular ring—solitaire rings, can spin if they're not exactly the right size. And if she's going to wear this for the rest of her life, fingers change!

What might be best is if you put on a thin rouse for your roommate. Say you're buying a ring for your mom's anniversary/sister's birthday, and gee, you seem to have the same size hands! What size ring do you wear? Plus, if she sees through the rouse it gives her a bit of advanced warning. I don't value a jaw dropping surprise proposal more than one she's had some time to internally process and confidently say yes to.
posted by fontophilic at 5:59 AM on February 28, 2014

8 not at all average. 8 is big. I have average fingers and I'm a 6.

Yes, this. I'd say 5.5-6.5 is average - 8 is really big.
posted by schroedingersgirl at 6:03 AM on February 28, 2014

Best answer: In this case, I would much rather be surprised than not. And if I weren't going to be surprised, I would want to be told during a conversation with my boyfriend, not with my roommate who then told me to act surprised. I think it would be terrible to act surprised during the proposal. So I would encourage you to not do this.

I wouldn't care if you went through my stuff, so there's no element of invading my privacy concerns with me. Root around in my dresser drawers for all I care. I mean seriously, you, Durin's Bane, can come over right now and look through my stuff if you want! But it sounds like finding a ring wouldn't be all that helpful anyway. Maybe suggest to her boyfriend that he get a toy ring or a replaceable ring and then take her to get her ring size.
posted by lyssabee at 6:22 AM on February 28, 2014 [1 favorite]

Best answer: I think you should either politely decline


or tell the roommate what's up.

Please don't do this.

It's a surprise for a reason. Telling her (and spoiling it) is not cool. Just because he doesn't get the ring size doesn't mean he can't still surprise her.
posted by mr_silver at 6:35 AM on February 28, 2014 [2 favorites]

I measured my then live-in-girlfriend's ring for this purpose. Turned out the fool thing was a pinky ring. As many above have said, you can't guess ahead of time without asking for confirmation. He should just make sure the ring is from a place that will resize *or replace* as needed, with no caveats or conditions.
posted by jeffjon at 6:46 AM on February 28, 2014

I don't think it's at all weird he asked you to find her ring size - I think it's quite lovely actually!

A Size 8 ring is HUGE. Apparently 90% of women are a size 6

I don't necessarily think it's THAT big of a deal to gently go through your roomate's stuff. It's not as if she's going to keep her jewellery in a really random spot, you'll either find her jewellery stash fairly quickly or you won't.
If you don't find it quickly you can just leave - at least you've tried.
I guess I'm trying to say I wouldn't mind if someone went through my stuff with this end goal in mind - your roommate may be different but only you know if she's likely to be pissed off if she finds out!
posted by JenThePro at 7:28 AM on February 28, 2014 [1 favorite]

Best answer: I have to say, sometimes the MeFi consensus view strikes me as incredibly uptight, proper-at-all-costs: basically, a killjoy pile-on. In the same way that MeFi always tells you to break up, always tells you to get a lawyer, doctor, therapist and to dump out the old mayonnaise you've been wondering about, these are stock answers, given to you by the safe group consensus that never breaks the rules and leaves nothing to chance. Growing up, this was the voice of those boring kids who did whatever mom said (and probably tattled to boot).

So fuck that. Helping with a surprise proposal (that she is talking about already) is a gesture out of pure positive goodwill and love. This is a lovely favor, meant with the best of romantic intentions. Help the guy out, do the best you can, be creative! (Take all the warnings about ring sizing to heart), but jump in the fray here and do your best for your roommate, for her guy, for love.

A year ago, my boyfriend's coworker helped snoop to discover his business trip travel interary, and sent it to me. Thanks to that "violation" it helped me plan the most romantic weekend of our lives. She was THRILLED to help me, he was touched that she did so, and I needed the help to pull off that extraordinary coup.

Let love win for once, over the rule-makers.
posted by amoeba at 3:21 PM on February 28, 2014 [6 favorites]

If you do decide to snoop: better cross your fingers that she doesn't keep her jewelry in her dildo-drawer next her spank-bank of printed photos of her nekkid boyfriend (aka your friend).

Unsee all THAT if you can.
posted by nacho fries at 6:24 PM on February 28, 2014

Okay, I'm a girl and I looooooove surprises so:

1) Do NOT do/say anything that will spoil the surprise
2) Do NOT pretend to be asking about someone else's engagement-- she will put 2 and 2 together.

I totally think the "hey I'm looking at a ring on Etsy" or "let's go to the mall wtf why is my ring size weird you try it!" OR another option: get a ring sizer, leave it around the apartment and be like "wtf is this? [girl friend] left it here," and then get her to use it, would be passable-- she's probably thinking about rings in the back of her mind if she's discussed getting engaged, and hopefully will be thinking "hmm I wonder what size I am" and not "Boyfriend put you up to this!"

TBH, if you know where she keeps her rings, I think snooping is OK. No one has to know, anyway. Either boyfriend tells her because it's cute, or no one says anything and he's like "heh I guessed! I'm a savant." I know some people (here, at least) would feel crushed by this kind of lie, but hopefully you can tell if these two are those kind of people.
posted by stoneandstar at 10:32 PM on February 28, 2014

If she has an easy-to-access place where she keeps her rings, I'd grab one and size it, no question. You can even print out a ring sizer diagram, but I don't know how accurate it is.

If you do grab a ring, you can race to the nearest jewelry store and get it sized and get the ring back into the jewelry box in no time. Just try, if possible, to use a ring that she wears on her ring finger. IF you can.

But please don't play any games with her about rings and ring sizes. Her sweetheart wants this to be the greatest surprise he's ever pulled off and she's worth it. After he gives her the ring you can tell her how he got the size, apologize, etc., but I don't think you'll need to. Just give her a rousing big hug and happy congratulations and it'll all work out perfectly.

posted by aryma at 11:34 PM on February 28, 2014

Response by poster: Any mention of rings or gimmicks to get her to try something on would be laughingly transparent based on my personality and our interactions. I opted to do a 30 second visual inspection of her room. Saw a jewelry box with a glass top, no visible rings. Told the boyfriend I tried but no luck and that most jewelers will resize for free.

Thank you everyone for helping me think this through more.
posted by Durin's Bane at 2:07 PM on March 1, 2014 [4 favorites]

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