20 Twenties Tweaks: #17 - Shall We Wed? How to Propose Marriage to Your Partner
Ultimately any proposal has one goal in mind: we both want to get married. Her saying Yes is the intended and ideal outcome.
One has to be an optimist to believe in the idea of marriage in the first place, but you have to be seriously optimistic if you’re considering proposing. That brings me to the first, and biggest, part of any plan to proposing: be confident that she’ll say yes.
If for any reason you have reasonable doubt that she would not accept your proposal to marry then full stop right there. Work on your relationship; give it time. It’s like free throws in this way, you need be to shooting way over 50% and confident enough that the next one is going in, your team needs this to win the championship, be sure to have a steady hand.
This is all because even the most sure people planning to propose will be nervous. You’ll be nervous since the idea first ever creeps into your head and it’ll stay there through every step of the process. You think the person being proposed to looks happy they’re engaged? Look how relieved the person who popped the question looks - they’re done.
Simply put - Proposing is unnatural, despite how normalized and celebrated the act is in our society and culture. Spending thousands on a ring, a plan, and a hope is one thing and getting down on one knee to propose you both spend even more money on a wedding, then a house, then a pet, then a baby, then take care of each other until death is another thing. It’s crazy, awkward, uncomfortable, insane, and yes romantic. You will be nervous about asking if this means anything to you.
But you shouldn’t be nervous that she’ll say Yes. This proposal may come as a surprise to her but it shouldn’t be a shock. You would have been looking for the signs, the way you both had talked seriously about the future. The ways in which you feel like she’s given you The Green Light. Women, if you haven’t given a Green Light, whether that’s not so subtly dropping hints, talking marriage, or sharing how YOUR FRIEND got engaged and you liked this that and the other thing about how that went, then do so. Give a Green Light and then give him some time.
Because after a Green Light is received comes a Behind the Back conversation with her Best Friend. If you don’t know which best friend she intends for you to conspire the proposal with then maybe that’s a sign you don’t have a Green Light for Yes yet. (Pro Tip: if she was involved in a Behind the Back conversation about a friend’s engagement, maybe it’s that friend.) Talk to this friend, if they aren’t surprised you’re calling about this, if they’re genuinely excited, then you’re on the right track.
This friend will be your emotional support system and should build up your confidence that This Will Work. They’ll coach you on how to ask the parents. Basically, you should have a relationship with her parents already and know how they’d want to be approached, on the phone or in person. Do it.
Make small talk and get into the reason for the call. You love their daughter and want to make a life with her. Get their blessing. If they aren’t surprised or withholding, then that’s another good sign. My advice would be to ask if there’s a family ring you should use. Cant go wrong with a family ring.
Now you need a ring. Between her Best Friend and Mother (the two should also have an existing relationship) there should be a consensus on what ring to use. A family ring is sentimental (and free). A new ring is fine, if you’re confident in her jewelry style. She’ll be happy with any ring, but you want her to love the ring she’ll wear the rest of her life, so allow her the flexibility to settle on something different after proposing. If you already have strict specifics, follow them to the letter, may the jeweler have mercy on your budget. Make sure you have it sized to fit (ask the Mother) or just a little bigger, to be safe - you want that to fit around the finger in the moment.
Once you have the permissions/support, a ring, and the confidence of a Yes, then you need a plan. Because while this is a very private decision between the two of you, it will also become The Story she’ll tell over and over the rest of her life, for good or ill. So you want to give her a story with the proposal and that’s commendable.
The most important thing when planning the proposal is to make it representative of your relationship. It should not come out of the blue. Don’t do it at the beach if you never go to the beach. Don’t do it at a sporting event if she doesn’t like sports (or being the center of attention, or being peer pressured, or your team is losing, actually don’t do this at all). Don’t do it at an ice cream shop if you never get ice cream together. To thine own self be true. You get it.
Run this plan past the Best Friend. Pick a date, an upcoming event, but don’t be too obvious. Best if it fits into something you’d naturally be doing together, so the surprise stays intact. No one will want to spoil it, but it’ll be hard. For your own sanity don’t have it be too far off. Once you have the ring to hide it’ll burn a hole through you.
Confirm the plan closer to the date. It’ll give you the nerves to go through with it because you won’t want to let others down too (but trust that if it’s not feeling right you’ll back down and postpone the proposal, and it’s be for a reason strong enough to convince your support you were right). Don’t over-rehearse. Don’t try too hard. Save room to be in the moment for your moment.
Have a great experience with your potential future legal partner. When the time feels right, when it feels YOU enough, do the damn thing. Be nervous, don’t worry about having the words be perfect, but stick the landing.
Ask her. She should say yes if you’ve made it this far together. Celebrate. Relax. (Don’t worry about planning the wedding right away).
Breathe out. Relax.
*I’m posting daily one hack/tweak I’ve discovered and integrated into my life during the last decade as I lead up to my 30th birthday on the 28th. Here’s all of the #20sTweaks so far.
**PS - the photo is one that Lauren Farmer took of us after I proposed to Andrea on her old rooftop in Manhattan. It’s not an extremely accurate recreation, but a fun one nonetheless. Here’s that story.