You’ve been dating for a while. You’ve passed by all the typical milestones: met their friends, had dinner with their folks, claimed a drawer and have a toothbrush at their place. And now, the holiday season has passed and your ring finger, while beautifully polished and manicured and begging to be adorned, is bare. What gives? You’ve been dropping all the “propose-to-me-already” hints, right? Proposing takes a lot of confidence, and it could just be that your love needs to be sure you’re ready to say “Yes”! Here’s some confidence boosting ideas to get your boyfriend/girlfriend down on one knee.

A Subtle Approach

Custom etched wine bottle by The Copper Pine

Subtlety. It’s a hard thing to master, and between the two sexes, it can be a hard thing to pick up. You may be thinking that you are dropping lovely little hints about getting married, and they are clueless. But, a slow and steady approach is a good way to begin. Start dropping small hints throughout your day. Bring up the “M” word by talking about one of your newly married couples, showing them a picture of yourself when you were a flower girl/ring bearer, or cuddle up to a movie with a wedding. Maybe make sure it’s one that ends well, no need to send the wrong message! The important part is to start making words like “wedding,” “marriage” and “future” part of your casual dialogue. One of my favorite nudges is for when you think they’re almost ready: when you guys are talking about your weekend plans, mention that you have plans to go to *insert whatever jeweler you like best* to get your favorite ring cleaned, getting it resized is even better. That little bit of information tells them where they should shop, and if they realize it, you’ve given them your ring size. Look at you, being the Queen of subtlety.

Visual Encouragement

Some people are audio learners; many are visual. This is a pretty easy one. Sit down with a glass of wine and watch a few episodes of “Say Yes to the Dress,” or whatever wedding-centric show you like. One episode won’t do, they need to get the hint that you are really interested in the dresses/cakes/whatever. Gush about your friend’s new ring “Oh my gosh, that princess cut/solitaire/white gold ring is GORGEOUS!” or go ahead and create a profile on a site and leave your iPad unlocked for them to see. By giving them specifics, you will make them feel surer of themselves when it’s time to shop. Yes, they may roll their eyes when you’ve shown off your bling for the 100th time, but secretly they’ll be giving themselves a pat on the back for making you so happy.

Talk About It

At some point, the two of you are going to need to simply talk about getting married. Having a real conversation about what you want out of life, and out of a partner, is an essential step for both of you. After all, you don’t want to say “yes” just because you are ready to be married only to realize that those three kids you’ve been dreaming of are nowhere on your fiancé's radar at all. If the two of you can make it through these conversations, and come out on the other side still seeing each other in your futures, then you’ve just made a huge leap towards introducing each other as your “fiancé.”

Drawing a Line

Some people can live their entire lives with another person, and remain completely unattached, legally speaking. However, since you are reading this post, I don’t think that applies to you. There are so many factors to consider when you decide to draw the line and put forth an ultimatum. Generally speaking, I think this should be a last resort. Ultimatums bring out a person’s “fight or flight” mechanisms, and unless you are truly ready to accept both options, you shouldn’t use them. That said, you can’t spend your life waiting for someone to maybe commit to you. So how do you handle this?

First, be reasonable. You shouldn’t be hitting your first anniversary as a couple and expect to be married this time next year “or else.” That’ not realistic or fair. For starters, let’s just say that your love IS ready to propose, you’ve been looking at engagement rings, you know how expensive they are. Not everyone has the savings to drop a few (being modest here) thousand dollars at the drop of a hat on a diamond. Be open to a date that is about a year out. If they’re serious, they’ll get some gumption and get it together. But, as I said before, be careful with this one and be reasonable. Pushing ultimatums is not something that should often be done or without careful consideration.

Don’t forget; you’ve got another option… go get what you want! Gather up your courage, start planning that proposal, and get ready to pop the question. Good things come to those who wait, but that doesn’t mean you can’t help things along!

Side bar: If you are a dude reading this. Yes, she wants you to hire a photographer to capture this once in a lifetime experience.

Additional side bar: If you need help planning, I highly recommend LCM Weddings. She offers proposal planning services!