Deciding on the Basics
Make sure he's ready for marriage. Before you decide to propose, make sure marriage is on the table. While you do not want to ruin the surprise, you need to at least make sure your boyfriend is interested in marrying. Work marriage into your conversations to get a sense of whether proposing is a good idea. You can bring it up directly. For example, say something like, "Do you think we'll ever get married?" When discussing marriage, bring up the topic of a proposal. Say something like, "Do you like the idea of a formal proposal?" Some people prefer to get engaged together as a couple. Try checking with a close friend of your boyfriend's to see if he has ever brought up the idea of getting married.
Figure out what his dream engagement is. See if he wants a surprise engagement, if he wants you to propose to him, or if he'd rather have a conversation first. You can bring this up casually well in advance of your actual proposal, so that it is something you both know about one another. You might say, "When you imagine getting engaged, what do you picture?" or "Do you have any friends with really great engagement stories?" If you don't think your boyfriend would love a traditional surprise engagement, think about ways the two of you could mark the occasion together. For instance, he may want the two of you to pick out engagement rings together.
Add a twist to what your boyfriend would want. Think about what your boyfriend would want in terms of a proposal. Maybe your boyfriend has brought up the subject before. Try to honor his wishes, but provide a small twist. This will help keep the surprise and add something extra to your boyfriend's dream proposal. This can be especially nice if the proposal is not entirely a surprise. If you agreed to get engaged within a certain timeframe, for example, your boyfriend may be expecting the proposal. For example, maybe your boyfriend always dreamed of getting engaged on a romantic vacation. Take him on a trip but do not propose on the trip. Instead, pop the question on the airplane on the way there. Maybe your boyfriend admitted he would like to be proposed to at the coffee shop where you first met. Instead of simply asking him there, surprise him by having a group of friends meet the two of you there holding a sign that says, "Will You Marry Me?"
Pick a location. To start, think about where you want to propose. Think about what your boyfriend would want and find a place that's special and meaningful for both of you. Where is somewhere that was or is special for the two of you? You can also define your boyfriend in a couple of words to get an idea of what would suit him, such as traveler, adventurer, romantic, philosopher, etc. This can help you to narrow down your options to identify something that will be meaningful to him. Would your boyfriend want a public or private proposal? If he wants something private, think about a special place to propose without onlookers. You can propose at home and decorate your house with things like candles and photographs of the two of you. You can also go some place private together, like a secluded hiking trail where you've gone on hiking dates. If your boyfriend wouldn't mind a public proposal, think about public places you both enjoy. You could propose at the coffee shop where you had your first date. If your boyfriend dreams of a proposal in front of friends and family members, ask him to marry you at a dinner party with friends.
Choose the right time. Think about important dates. You can choose a date that's significant for the two of you. For example, propose to him on his birthday or your anniversary. You can also choose a date that makes logical sense regarding future plans. For example, if you want to be engaged by his cousin's wedding in March, consider proposing some time in January or February. Try to think of a unique date if you want something memorable. Instead of choosing your anniversary, choose another significant date. For example, propose to him on the anniversary of when you two adopted a kitten together.
Think about whether you want a ring. Do you think your boyfriend would prefer an engagement ring? Many modern proposals do not use a ring, but if you think your boyfriend would like one you can find one in his size. If you don't want a ring, many people choose another item to symbolize the proposal. You can get him another piece of jewelry, such as a watch, or just give him a gift to mark the occasion. If you can think of a meaningful gift he would really value, such as a musical instrument he's always wanted, go for that. You can use the gift to propose. For example, tape a sign that says, "Will you marry me?" on a guitar you got him.
Dealing with Potential Stigma
Consider your boyfriend's feelings on tradition. Traditionally, men propose to women with rings. Many people feel men will propose when they're ready and women should wait, and that breaking this tradition is a bad thing. If you're a woman proposing to a man, you're breaking tradition slightly. Think about how much your boyfriend cares about you taking the lead. Many people worry they will be stealing their boyfriend's thunder, or pressuring him into something prematurely. If your boyfriend is truly ready to get married, and is not big on traditional gestures, it is probably okay to propose. However, if your boyfriend or his family are more traditional, bring up the issue in conversation. Ask your boyfriend how he feels about women proposing to gauge his potential reactions. You can also think about his attitude about gender roles and consider whether he is more traditional or open-minded about proposing.
Think about how to adjust the custom as needed. An engagement follows a traditional narrative. The man proposes to the woman, usually with a ring. If you're in a same sex couple, or if you're a woman and proposing, you do not have as many set customs and traditions. Think about how you can alter custom to make things work for you. There is nothing wrong with getting a man a ring to propose. You can select something cut in his style and opt for the tradition down on one knee proposal with a ring. However, some men do not like jewelry. You can choose another object to present him, or you can simply ask him without an object. One of the benefits of a non-traditional proposal is there are less expectations. See this as a positive rather than a negative. You are following your own narrative and can propose on your own terms.
Accept you may be nervous. Most people get nervous before proposing. However, when you're breaking custom or tradition, there may be an added layer of anxiety. Go into the proposal expecting you will be a little uneasy. Remind yourself why you've made the decision to keep yourself calm. If your boyfriend's traditional family is causing nerves, remind yourself of how happy you and your boyfriend will be after the proposal. This is about the two of you deciding to spend the rest of your lives together, and when you two are alone enjoying your engagement there will be little judgment or stigma attached. Rehearse what you want to say several times until you know it by heart and then remember to keep breathing when you speak these words.
Prepare for a range of reactions. In any proposal, there will be a range of reactions. However, with a non-traditional proposal, you may find reactions are even more varied. Some people will be shocked that you proposed to your boyfriend. Others will applaud you for breaking tradition. When you choose to announce your engagement, prepare for a range of comments. People have more opinions on non-traditional proposals than traditional ones. While some opinions will be positive, as many enjoy it when others break tradition, other comments will be confused and judgmental. Try to remember you made the decision that was right for you and your boyfriend. Some comments may be offensive. For example, if you're in a same sex couple, people may feel the person who proposed is more dominant or masculine. It's okay to correct people if they say something hurtful. For example, "Me and my boyfriend are equal partners. I just happened to have a great idea for a proposal before he did." Prepare ahead of time for what you might say if someone says something hurtful to you. This will help you to feel more confident if someone does say something hurtful to you. Also, keep in mind that you do not need to explain yourself to anyone. You can ignore rude comments or give short answers.
Recognize the decision is yours. Remember, you made the decision for the sake of your relationship. Even if there is outside judgment, you did what was right for you and your boyfriend. The two of you are happy and going to spend the rest of your lives together. That is what matters, not any outside judgment you receive.
Proposing Successfully
Set the scene. Think about how you want things to look. Talk through your ideas with a friend to help you make sure that you have not overlooked anything. It's also okay to ask your friends for help with executing the proposal. If you have control over the scene, set it as much as you can. Remember, you can't control everything, but you can get things somewhat close to your vision. If you're proposing at home, it's fairly easy to set the scene. You can dim the lights and light candles. You can also put up decorations, like pictures of you and your boyfriend. If you're proposing publicly, you have less control over the scene. However, there are some things you can do to get the scene you want. If you're proposing on a hiking trip, hike at the right time of day so you'll reach your destination right as the sun is setting. If you're proposing at a restaurant or coffee shop, try to get the right table.
Introduce the ring or object, if you're using one. If you're proposing with a ring or another object, find a way to introduce it. You can hide a ring in your pocket or purse and lift out the box when you're ready. At a restaurant or coffee shop, you can have the ring brought out by the waiter in a drink or item of food. Other items can be introduced creatively, depending on what they are. For example, if you bought your boyfriend a nice watch to propose, think about having him close his eyes and then slip it on his wrist. If you're presenting a ring, think of a fun way to do it. For example, you can leave clues around your home leading him to the ring.
Ask the question. You can keep things simple. Look in his eyes and tell him something about how much you love and treasure him. Then, say something like, "Will you marry me?" Some people prefer proposing in a letter. You can compose a brief love letter and hand it to him. Have the words, "Will you marry me?" written at the end.
Handle a rejection gracefully. Sometimes, things do not go as planned. If your boyfriend declines, do not see this as the end of the relationship. There are many reasons someone may not want to get married, some of which may be rooted in practical concerns. For example, maybe your boyfriend wants to wait until you're more financially stable to marry. If he says no, calmly talk it out and figure out where to proceed from there. Keep in mind that you don't need to talk things through immediately. You can take some time for yourself. Just make sure to come back to the conversation eventually. Remember, you would rather have your boyfriend marry you when he's truly ready than say "Yes" just to make you happy. It's better that he thinks about it first to make sure it's what he wants.
Keeping Things a Secret
Tell a small number of close friends. It can be helpful to have people in on your plans. This is particularly important if you need someone to, say, get your boyfriend to the right location at the right time. However, if you want to keep things a surprise, minimize the amount of people you tell. Stick to telling a small circle of friends who you know can keep a secret.
Keep him distracted. In the weeks leading up to your proposal, keep your boyfriend distracted so he doesn't expect anything. Find ways to keep your boyfriend busy so he doesn't notice you're caught up in planning something. Try to encourage him to try new things. You can even do new things with him, if it doesn't interfere with your plans. For example, take a cooking class together or start a new workout routine. Have your friends help. Ask that the friends who know about the proposal take your boyfriend out more often in the weeks leading up to the big day.
Have excuses ready. Your boyfriend may sense something is up. Be ready to quell his suspicions with stories. Think of ways to excuse unusual behavior. If you're out shopping for rings, for example, have your friends say they're taking you on a spontaneous shopping trip.
Do not plan for too long. Try to minimize how long you plan the event. The longer you spend planning the event, the more your boyfriend will suspect something is going on. Try to only plan the event for a week or two before you pop the question. This will keep things from becoming stressful. A proposal should be a fun event to celebrate your relationship.
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