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How to Propose to Someone Who Is Hard to Surprise

You’ve found the love of your life and are ready to ask him or her to marry you, except for one thing: your S.O. is impossible to surprise.

Photo: Kelli Boyd Photography

You’ve found the love of your life and are ready to ask him or her to marry you, except for one thing: your S.O. is impossible to surprise. They can always guess when or how something will happen (and they’re usually right), and they’re so observant that they notice every minuscule, out-of-the-ordinary detail. It might take a bit of extra planning to come up with something that will catch them off guard, but there’s no need to completely stress yourself out (that definitely won’t help anyone!).

If you’re left wondering how you’re supposed to pull off the perfect proposal right under your partner’s nose, follow these steps.

Look for distractions
The less time your significant other has to think about the proposal, the better your chances are of keeping it a surprise. Spend time as a couple doing new things that require a basic time commitment, like starting a workout plan together, attending weekly art classes, or even tackling a to-do list for your apartment/home. The distractions should give you some wiggle room to coordinate your proposal, and bonus: the two of you will get to spend some quality time together in the process.

Keep your circle small
To avoid the risk of spoiling the surprise (especially if your S.O. likes to snoop around for info), be very selective about who you share your plans with. It can be hard to keep something so exciting to yourself, but even the most well-intentioned friend could accidentally slip up and spill the beans. A good rule of thumb: only tell the people who absolutely need to know. The fewer, the better.

Create a false trail
Anything that’s different from your usual routine will raise a red flag on your S.O.’s radar, so the key is to plant a few decoys here and there to trick them into thinking they know the whole picture. If you know you’ll be out shopping for an engagement ring one weekend, tell your partner ahead of time that you’ll be busy—a friend needs help painting his apartment, you picked up a few extra shifts at work…you get the drift. Just make sure that your alibi is a reasonable one, and avoid coming up with something vague at the last minute. Saying “I’ll be out running errands all day” without an explanation of what you’re doing will definitely cause suspicion.

If you’re proposing with a ring, chances are that your S.O. will want to show it off with a #justsaidyes selfie. Tricking them into getting a manicure before you propose is a sweet idea, but it can seem too obvious if it isn’t something your partner does on a regular basis. In that case, recruit one of their close friends or relatives (someone super-trustworthy) to help you lay the groundwork a few weeks ahead of time. A “spontaneous” mani-pedi date with their BFF right before you propose won’t seem so out of the blue if it’s something they’ve already done a few times.

Do what they’re expecting, but with a twist
If your significant other has shared their idea of a perfect proposal with you, it’s completely fine to stick with whatever they’ve mentioned. At least you know what will make them happy, right? But if you hate the thought of being totally predictable, it’s okay to switch it up a bit, too. For example, if they want to get engaged while surrounded by family and friends, choose a spot where their loved ones can secretly watch you propose. Without a large crowd gathered, you can (hopefully) catch your S.O. off guard, and you’ll have the upside of celebrating with everyone immediately after.

In general, try not to stray too far from their original idea. If your S.O. has their heart set on getting engaged at a certain location or specific time of year, keep some element of surprise by incorporating that into the proposal without it being the main focus. Proceed with caution if you’re avoiding their wishes completely—someone who prefers privacy might not appreciate being cast into the spotlight with an elaborate proposal in front of hundreds of people.

Don’t string them along
When your partner is expecting you to pop the question, every moment the two of you spend together can start to feel bogged down by the pressure to propose. A romantic dinner date, a stroll through the park, or a weekend getaway are all good opportunities, but they’re especially obvious to someone who thinks they’re about to get engaged. You can throw your partner off by planning special outings as usual, but don’t propose at the very first chance you get. After one or two occasions, they might start rethinking any suspicions they had about an upcoming proposal. While it’s okay to keep your S.O. on their toes for a little while, don’t drag it out too long. You don’t want them to start thinking you’re toying with their emotions.

Talk about it beforehand
Many couples (about 46 percent, according to WeddingWire’s Newlywed Report) shop for an engagement ring together, and some choose to skip the proposal entirely. If you're wondering how to keep the proposal a secret from your partner, this might be a good alternative for you, since it eliminates most of the surprise from the start. Even if you purchase the ring(s) together, you can still surprise your S.O. by not telling them when or where you’ll officially pop the question. Have an honest pre-proposal talk with your partner beforehand to see what they’re thinking.

Go for the obvious
In the end, sometimes the best way to pull off a surprise is by going with the obvious. If someone thinks you’re going out of your way to plan a top-secret proposal, it’s easy for them to overlook what’s plain as day right in front of them (they’re too busy trying to figure out what you’re up to!). However you choose to propose, remember that it will be a romantic and special moment for both of you, surprise or not.