Let's be practical: An engagement ring is a big investment, and unlike most jewelry that goes in and out of style over time, this is one piece that should look and feel timeless. Make his search for the perfect ring easier by dropping the right clues.
1. Show Him a Picture
Find clever ways to show him a picture of your favorite setting, cut, and style. A Valentine's Day card works, and a web page left open to your dream ring should definitely get the point across. A subtler way: While perusing magazines, point out pictures of rings you like and casually mention what you like about them.
Timing tip: Don't show him pictures before he's prepared to buy a ring. If he's not ready to propose, then showing him a photo of the exact ring may make him super uncomfortable and reluctant to shop. The picture route works best if you've made it clear to one another that you plan to get engaged.
2. Shop Together for the Ring While walking past a jewelry store, casually express interest in stopping in and taking a look. Depending on the store, the salesperson will likely ask if you'd like to try anything on. Decide on a time to formally shop for rings together.
Timing tip: If he's a traditionalist, he may be opposed to shopping for the ring with you. If this is the case, consider going "window-shopping" with him, so that there's no pressure to buy while you're out together. That way, he can go back and buy the ring on his own.
3. Have a Friend or Family Member Go with Him
You're too reserved to point out the ring yourself, but your best friend or close family member knows your style, and you completely trust their taste. Let your close friend or family member know what you like and don't like. If there's one ring in particular you love, tell your friend. When it seems like he's fishing for ring hints, you'll be able to confidently send him to talk to your close confidante.
Timing tip: Let him come to you for hints instead of pressuring him to talk to your family or friend, which could be intimidating.
4. Ask for a Surprise
Mention your favorite settings, cut, color, and style to make it clear to him what you like. Then put the ball in his court by telling him that you love his style and you're sure he'll choose something gorgeous. And, just in case, make it clear if there are ring styles that you would never wear.
Timing tip: Patience is the key here. Pulling off a surprise, romantic proposal takes planning, so don't prod too much.
5. Design It Together
Make it clear to him that you would like a custom-made ring before he proposes. Then come up with ring ideas together and make it a couple's project. Make sure he has a say too -- ask him what he thinks about certain elements and incorporate his suggestions into the overall design. Do research to find a designer that you both like, and then commission the ring together.
Timing tip: Once the ring is ready, decide whether you want him to hold onto it for a formal proposal or if you'd like to start wearing it right away.