Same here. I tried the friendly gift giving option but it didn't register in the aspiration. There is no option to gift the jewelry when clicking on it in inventory. I also saw someone mention an "offer jewelry" interaction in the affection section of the pie menu, but that doesn't come up for me either. The jewelry isn't charged, and I'm really not sure what I'm supposed to do. I'll keep trying things but I really wish it wasn't so finicky.
You can Gift Jewelry... from the Friendly > Affection menu. (Gift Jewelry
You can Propose with Crafted Ring from the Relationship menu (used to be in Romance before Lovestruck.) provided you aren't a Lovebug.
If you are a Lovebug, if you have a crafted ring in your inventory, you have two options to Propose Early, one of which will be with a crafted ring, but you can't tell which one it is. Click on the wrong one and you propose without gifting the ring. (I have reported this in a separate bug report.)
If you have a crafted ring in your inventory, you can click on it to Propose with it. (This works whether or not you are a lovebug.)
Any of the above will satisfy the Give Gift of Jewelry aspiration goal. (Basic rings purchased through the phone's Shopping > Purchase Romantic Items menu count as crafted rings for this aspiration goal.)
What you can't do to satisfy the aspiration goal is to gift jewelry romantically except by proposing with a crafted ring.
