As founder of the proposal website HowHeAsked.com, I’ve heard thousands upon thousands of proposal stories. A good amount of the stories start with, “I knew it was going to happen, I just didn’t know when…” That’s because these days getting engaged is more of a conversation than it used to be. Gone are the days where the question isn’t rhetorical.
That being said, one big hurdle you have when you’re planning your proposal is to actually, truly, seriously surprise her. Here are some ways to do that.
1. Make “plans” for you or her and give her specific details about said plans.
Example 1: Tell her you have a work event that evening. Tell her that “so-and-so” is going to be speaking (“remember the VP I told you about that has the triplets… he’s the one speaking”).
Example 2: Have a friend plan a sorority sister brunch (or something). I would try to have a not-so-close friend suggest the plans and then have a closer friend encourage that they go together.
2. Go to the mall a day or two before, pass by a jeweler and suggest you look around so you can “get to know her taste.”
At this point, you already have the ring in your desk at work. This strategy is definitely a bit risky but if you can keep a straight face, it can really throw off the timing of her expectations. She’ll be shocked when you pull out the most beautiful ring she’s ever seen a mere two days after she convinced herself you obviously hadn’t even started shopping yet.
3. Tell her you’re waiting for another milestone before you get engaged.
As we mentioned above, getting engaged is often talked about many times before it actually happens. When it gets brought up next, have a “serious” conversation with her. Tell her that you love her and that you’re just as excited to get engaged as she is, but that you want to make sure “xxx” happens before that. Perhaps it’s that you get a promotion at work or that you move in together beforehand. Reassure her that it will happen (don’t be a you-know-what and pretend you’re not sure), but that there is an understandable milestone for you to hit first.
4. Suggest you take a trip together a few weekends after the date you plan to propose.
Let’s say you’re planning your proposal for July 10th. A few weeks before, tell her you want to take her somewhere the weekend of July 17th or 24th. She’ll immediately think it’s going happen on the trip (and so will all her friends and family), and she’ll be royally stumped when it happens anytime before that.
Want to hear other ways men have done it? Head to HowHeAsked.com to read tons of real-life proposal stories from guys just like you.