How to Pop the Question: A Man’s Guide to the Perfect Engagement
Whether you’re childhood sweethearts, found love at work, or both swiped right, you’ve found the one and you’re ready to commit to them for the rest of your life. Which means it’s time to figure out how exactly you’re going to pop the question. This is a huge task and can be daunting to think about, but your proposal will be flawless as long as you plan everything properly.

If you’re fretting about how to approach this, our guide to planning the perfect engagement is here to help you along.

1. Make sure you’re on the same page

An obvious but incredibly important starting point is to make sure you’re both ready to tie the knot, so talk to your partner about the future. You need to let them know that getting married is something you want to do and check whether it’s part of their future plans too. If you’re worried that this conversation could sound too much like an actual proposal, keep it general by discussing somebody else’s engagement and go from there. 

This is a life-changing question that shouldn’t come out of the blue. You don’t want your partner to be caught by surprise, as this is almost guaranteed to prompt a hesitant “yes” or an awkward “I’ll have to think about it”. Not ideal. Don’t think that broaching the subject will ruin the magic of everything though. Instead of your loved one wondering if you’ll propose, they get to wonder when. It is also crucial that you’re on the same page about things like children and where to settle down before making this commitment—here are some of the questions you should consider asking.

2. Talk to their parents if they’re traditional

If your lover has indicated that you’d need to ask their parents for their blessing, then be sure to do it. This is almost certain to be the case if they’re from a more traditional background. Should this be important to your partner and their family, making the effort will stand your marriage and your relationship with your future in-laws in good stead. Wedding Bee’s guide to asking for a parent’s blessing will help ensure this conversation goes smoothly.

However, do make 100% sure this is something that your other half and family would like you to do. If they’re non-traditional and don’t expect they’d need to give permission, asking anyway may actually be a bad move. Many people now see this practice as outdated, believing it shows ownership of parents over their children. 

3. Choose the right engagement ring

Your partner will wear their engagement ring every day for the rest of your lives, so there’s no margin for error. If you’re going down the surprise route, you need to get a feel for what they’ll like. Pay attention to what they wear day-to-day and ask their close friends and family to give you some tips. When it comes to choosing a jeweller, get recommendations from people you know and make sure you’re buying from a reputable store with good reviews. 

Crucially, find out your other half’s ring size before making a purchase. If you don’t want to ask them outright, check their existing jewellery and give the jewellers details on their height and weight, as this should enable them to choose the right size. If not, you can always resize later. For a more comprehensive overview, read GQs guide to engagement ring shopping.

Of course, your partner may be very particular about their jewellery and want to be part of the process. After all, a ring is a huge investment, so what better way to ensure they’ll love it than going shopping together? If your loved one has a certain design in mind but would like to adapt to it their taste, then buying a bespoke engagement ring could be a smart move. As explained by the jewellers at Taylor & Hart: “Your relationship is one of a kind – why shouldn’t your ring be? A bespoke engagement ring allows you to really reflect the personality and style of its intended wearer.” They point out that these rings can be adapted in many ways, such as featuring your partner’s favorite color, incorporating their birthstone, or even including lyrics from a special song.

4. Plan the proposal

Once you’ve got the ring, it’s time to plan the proposal itself, whether that’s an intimate moment, a grand gesture, or a surprise surrounded by loved ones. Only you can decide what is most appropriate, but consider your relationship and individual personalities before you make a decision. Whatever you choose, make sure it feels genuine and suitable for both of you, and don’t be pressured by what others think.

Regardless of what your particular plan is, bear in mind that it should be personal to your partner and perhaps you as well. For example, you could return to the place of your first date, base the proposal around an activity they love, or play their favorite song as you propose. Finally, create a fake backstory to keep the proposal a surprise, plan a post-proposal celebration and—most importantly—choose the right moment. Don’t rush things just because dinner is almost over or the sun is going down. Always wait until it feels right.

5. Think about what you want to say 

While you don’t need to write out your speech word-for-word, it’s certainly a good idea to note down some of the main things you want to say. Putting your thoughts on paper will give you a sense of focus when you’re popping the question so that you don’t miss anything out or choke in the big moment. But at the same time, don’t just read from a piece of paper, as this will come across as insincere. Simply think about what you want to express beforehand and speak from the heart.

As for what to actually say when you propose, some of the main things you may want to include are why you love your partner, the moment you knew you wanted to marry them, and what your hopes for the future are. Of course, don’t forget the “Will you marry me?” part, and keep the overall proposal short and sweet.


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