Pick a proposal plan
You don't need a drone or a string quartet. You need a place that means something, a moment with no interruptions, and a plan B. Start with one question.
Private or public?
This is the decision that matters, and it's about them. Someone who hates being the center of attention will not enjoy a stadium screen, however much it cost. If your partner goes quiet when a restaurant sings happy birthday, you have your answer. When in doubt, go private and add people afterward.
Five plans that work
Each one scales from nearly free to as fancy as you like.
The place that's already yours
Where you met, the first date spot, the trail you always walk. It has meaning built in and you know the layout. Book: nothing, maybe a photographer. Risk: low.
The view
A lookout, a beach at sunset, a rooftop. Reliable and photographs well. Book: check sunset time and scout it at the same hour a week before. Risk: weather and crowds.
At home, done properly
Underrated. Candles, their favorite meal, no audience, no logistics. Good for private people and for winter. Book: an excuse to get them out of the house for an hour. Risk: almost none.
On a trip
Great backdrop, and you both remember the whole week. Propose early in the trip so you can enjoy the rest of it and stop guarding a ring in a hotel safe. Book: flights, and ring insurance that covers travel. Risk: carrying the ring.
Private ask, surprise party after
The best of both. You ask alone, then walk into a room where family and friends are waiting. They get the private moment and the celebration. Book: a venue or a friend's house, and one organized person to run the room. Risk: the secret has more keepers.
Book these at 5 weeks out
Photos
A hidden photographer runs $200 to $600 for an hour in most US cities. A friend with a decent phone and a long lens setting is free. Either way, agree on a signal and a spot.
The table or the tickets
Anything with a reservation. Tell the restaurant what's happening and they'll usually give you the good table.
The cover story
A reason to be there and dressed decently. "Work dinner" and "my sister wants photos" both work. Keep it boring so it doesn't invite questions.
Plan B, in one paragraph
For anything outdoors, pick the indoor fallback now and decide the rule for switching, such as "if the forecast shows rain at noon, we do it at home." Deciding in advance means you're not standing in drizzle negotiating with yourself.
Things to skip
Hiding the ring in food. Proposing at someone else's wedding or party. Anything that depends on a stranger's timing. Proposing on a holiday if a no would ruin that holiday forever, although if you've had the conversation you already know it won't be a no.