Welcome to The 12 Days of Thatz Not Okay, a special holiday edition of a regular column in which I school inquiring readers on what is and is not okay. Check back tomorrow for our next seasonal installment. As always, please send your questions (max: 200 words) to email@example.com with the subject "Thatz Not Okay."
Over the years I have picked up several pieces of very nice jewelry (earrings, necklaces, pendants) with a view towards giving them to the Right Girl. These are quality items I've bought or won at auctions or otherwise acquired (through legal means), that I've just kept in my closet—still in their original boxes, mind, not just sitting in a bag gathering dust. I might have been single at the time that I got them, or purchased them with a view towards giving them to the girl I was dating, only to have that relationship end before Valentines/Birthday/Christmas/Perfect Excuse Day.
Or, anyway, it should be okay—I hope it will be okay—because your intentions are good.
Based on the wording of your question (for example: "pieces of very nice jewelry" instead of "necklaces and necklaces for the wrist; what are those called?"), I suspect you have a job or serious hobby—Antiques dealer? Buried treasure scuba diver? Alchemist?—that brings you into contact with nice jewelry on a regular basis. I hope so, because that, more than anything else, is the secret ingredient that keeps this behavior from skidding off the rails into full-blown insanity. A man who sets aside particularly striking Art Deco rings that come through his antiques shop is a romantic eccentric with hoarding tendencies. (Yes, you are a hoarder. You're fortunate that what you like to hoard are lovely pieces of jewelry instead of lovely yellowed grocery store circulars from 1998 that you swear you are going to sort one day, but your thoughtfulness is actually a compulsion.) A man who goes to Jared once a month to buy Pandora bracelets for a girlfriend who doesn't exist is just sort of creepy.
A man who SWEARS he got all this jewelry through legal means sounds like a serial killer, so I would stop emphasizing that. There's a reason people say "I got a new couch" instead of "I got a new couch—through legal means."
I trust that, since you were acquiring these items with the intention of eventually giving them to someone (even if it was just "Leah Remini's character from The King of Queens—but a redhead!"), you haven't been indiscriminately buying up birthstone earrings, milestone-specific charm bracelets, and initial necklaces ("The J stands for 'Just wanted to let you know that I'm crazy about you, Carrie"). However, even if the jewelry you are planning to share is of the timeless, classic variety, odds are that not everything you picked will jibe with your girlfriend's tastes. Giving expensive jewelry is not usually a grab-bag "You go to war with the army you have" kind of scenario; part of the joy for givers is selecting things they really think this specific recipient will love, and part of the joy for recipients is pretending the giver has nailed it exactly. ("How did you know I wanted a necklace made of green and purple buttons of varying sizes?")
The safest option is just to resell the baubles and use the cash to purchase items specifically tailored to the tastes of your Best Gal, now that she exists somewhere outside of your brain. However, although this course of action is romantic, it is not very complicated, and you seem like a man who likes to complicate things for no reason. So let's hold onto that as a last resort and maybe someday we'll meet the perfect woman who just happens to love that sort of resort and then we can give it to her on St. Patrick's Day and she'll want to marry us forever.
Another option is simply not to tell your girlfriend how it is you came to acquire so many feminine baubles. When receiving a present—particularly on a holiday—people generally do not inquire into its provenance. (If you give her a pair of earrings on her birthday, she probably won't demand to know WHEN and WHERE they were purchased.) While safe for a Rico Suave type character—which you may not be, given your repeated tendency to break up with women before you have a chance to give them jewelry you have purchased for them—this option has a couple risks: for instance, if none of the jewelry you purchased is to her liking, she might wonder why you keep giving her rings filled with Victorian children's hair. You also might feel a little underhanded, though that's between you and your God.
The biggest risk (and thus the potential for the greatest reward) comes by telling her the truth: that she is in league with Croesus now, and that you would like to offer her but a taste of the unconscionable treasures you have hidden away in your storerooms. If she is almost incapacitatingly romantic, she will be touched, as you intend. If she shares your hoarding tendencies, she will be thrilled. If she possesses neither trait, she might just think it's unspeakably creepy, like buying accessories for your RealDoll.
One thing I would not do (assuming you and this woman have not yet mutually established some sort of long term commitment plan) is tell her that you have spent years storing up jewelry for the woman you are going to spend the rest of your life with, and you've decided that she's that woman, so here is the jewelry she's going to wear now, and you're going to start calling her "Jessica" because you always imagined you would end up with someone named Jessica. It's enough to simply say that you'd for her to have these pieces. (I would cut any reference to the fact that some of them were purchased when you were dating other women. "I was going to give this to Vanessa but then she cheated on me," is not the most romantic way to present a diamond brooch.)
Alternatively, you could toss all the jewelry in a box, plant it in your backyard, buy her a metal detector, and act shocked when you discover the trove of tasteful accessories dinosaurs must have buried there thousands of years ago.
Whatever you do, STOP ACQUIRING JEWELS UNTIL THESE HAVE ALL BEEN ALLOCATED. You are not a dragon!
Submit your "Thatz Not Okay" questions here. Art by Jim Cooke. Previously in 12 Days of Thatz Not Okay: 12 Bucks for Jim Fucking Beam; 11th Hour Bonus; 10 Dollars, Split Three Ways; 9 Christians Fretting; 86ing Grown-Up Christmas Cards; 7-ty Degrees Farenheit; and 6 Times a Troll.