Planning the Proposal
Figure out if you're ready for marriage. Marriage is a big step forward in your life, and you want to be sure that you're taking that step for the right reasons- because you've found someone you want to spend the rest of your life with, not because all of your friends are getting married, so you think that you also need to be. If you're looking to get married to 'save' the relationship or because you're scared of becoming alone, you should not do so. In fact, it's probably a good idea to let the relationship go. However, if you're certain that marrying this guy is in both of your best interests, then it's time to make it happen.
Talk about marriage with the guy. You should know how he feels about a committed relationship before popping the question. You don't necessarily have to talk about it in terms of the two of you (although you probably should), but it is important to know his position on this very important thing if you're going to be proposing to him. Pay attention to how he views the future. If he uses terms like "we" and "us" (referring to the two of you) when talking about his future plans, or if the two of you live together, own a pet together, or have moved in together, then he is likely committed to you. Find a way to talk about relationships in the general sense, or bring up your concerns in a potential, distant future sort of way. For example: "Becky just proposed to Henry in front of his entire family. I think I'd want to have a quieter proposal, don't you think?"
Keep the proposal about him. When you're planning to propose to a guy, you want to make sure that the proposal focuses on what he enjoys. For example, if you want to propose publicly at a fancy restaurant, that doesn't mean he will. You know your guy best, so make sure to keep what he would like in mind when planning the proposal. If he's really into fishing, plan a fishing excursion with him and put a note in the tackle box that says "will you marry me?" Or if he's a big fan of a certain band, plan your proposal around a concert or other place the band will perform at. This doesn't mean that you should ignore your desires completely. The proposal should be something that is memorable to you, as well; you'll just have to find a middle ground. For instance, you could follow the fishing date with a three-course candlelit dinner.
Plan the proposal. Spontaneity can be a great thing, but for something as major as a marriage proposal, it's more important to have the components figured out. You'll need to pick a specific place to pop the question, preferably somewhere that has meaning to both of you. It could be where you went on your first date, or it could be the first place you kissed. Picking a place that has meaning to you both works two ways, one, it's already special to you both and two, it provides a great segue into your proposal! Timing is everything. It's better to pick a time when he's relaxed and receptive to making or thinking about making a big change. It's less good to do it when he's stressed about work or school, or distracted by something else (like if you're both at a football game and he's paying more attention to the game than you and what you're trying to ask). You'll want to make sure that the mood is right for what you're about to do. It could be something as simple as lighting a few candles, or pouring out some nice champagne, or you could have a whole lavish dinner set-up. You'll need to consider what is important to the two of you. If you're including other people in your proposal (children, family members, friends, animals) you'll need to make sure that they know what they're supposed to be doing and when and especially that they need to keep quiet about it so they don't spoil the surprise.
Popping the Question
Use his hobbies. Again, when you're plotting how to ask him, think about his hobbies and interests and use those as a way to make the proposal special. Not only does this show that he's important to you (since you are, after all, asking him to marry you), you're also showing that you pay attention to his interests and that you support them. For example: if he's interested in archaeology, volunteer for an archaeological dig with him and propose on the dig (you can enlist your fellow volunteers to help). Or you could even make a treasure hunt type proposal and have him dig up the proposal in the backyard.
Pop the question privately. In every rom-com ever it seems, there's a scene where one person proposes to another and it's always in front of a bunch of people, but, especially for a guy, it's best to do this part in private (unless he's specifically said that he wants to be proposed to in front of a bunch of people). This way it gives him a chance to think about the proposal without the weight of a bunch of people waiting for his decision. Once he's said yes, feel free to go announce it from the rooftops.
Keep it simple. Even if you're planning an elaborate proposal (a skydiving extravaganza, or a scavenger hunt), try to keep the actual proposal itself simple and to the point. What you really need to do with it is tell him why you want to spend the rest of your life with him and would he want to do the same with you. You'll be nervous (because, who wouldn't?) so keeping it simple makes it easy for you to remember what you're going to say. Have a few lines to lead up. You could say something like, "We have so many awesome memories... From now on, I want ALL my memories to have you in them." and propose. Or, before your day, "I have this wonderful day planned for us, but I just can’t wait... I want us to spend it together as more than just boyfriend and girlfriend" and then propose.
Give him a symbolic gift. You'll want to give him some sort of symbolic gift, like an engagement ring, but it doesn't necessarily have to be a ring, especially if he isn't the type to wear a ring. You know your guy best, so you'll have to decide what the gift should be, but there are lots of options. You could get him a wrist watch or pocket watch, because these are sometimes considered the male form of jewelry anyway. You could even have it engraved with both of your names to make it more special. You could make something handmade for him, like a box containing all your favorite memories together, or a ceramic plate that asks him to marry you. If he's the type who wears necklaces, you could get him an engagement necklace, perhaps even with a ring on it. Engraved lighters are also, often, used as engagement gifts for men (or women) and can be very cool and attractive.
Deal with the aftermath. As you can't control the outcome, proposing to someone can be very nerve-wracking and make you feel vulnerable. That's no reason not to do it, but you have to be prepared for every eventuality. If he says yes, great! It's time for a party. You can set the wedding date, or leave that until sometime in the future (you don't have to get married right away, just because you got engaged). If he needs time to think, that doesn't necessarily mean he's going to say no. The proposal may simply have caught him by surprise and he really does need to think about what it will mean. Let him do that. If he doesn't get back to you, talk to him about the proposal and what his concerns are. If he says no, you are going to feel upset and you have every reason to ask him what his reasons are and if will ever change his mind. It could simply be that there is too much going on at the time (school, a big move, his parents are ill) and he can't think that far ahead, or it could mean that he doesn't want to get married. Whatever the reason is, you're going to have to make some choices about your future, as well. It could be that the two of you aren't compatible and don't have the same life goals.
Getting Creative
Set up a treasure hunt. You could have it be a treasure hunt of all the places around your city that are important to you, or a treasure hunt that plays on some of his hobbies. There's no wrong way to do a treasure hunt (unless it's too hard and he can't complete it). He'll be having a great time and be in fun mood for the last clue (the proposal).
Do a food proposal. Lots of people like a good proposal that has to do with food (as long as he doesn't end up eating the proposal by accident!). There are lots of ways to use food to make a fun marriage proposal. There are ways to have personalized fortune cookies made. You could have one made that says 'Will you marry me?' and make sure it gets mixed in when you get take-out (or if you make some lovely Chinese food). Hide a note and symbolic engagement gift (not necessarily a ring) amid a box of delicacies and give them to him. Again, make sure he doesn't eat the note or the gift by mistake.
Propose through pumpkin carving. Around Halloween go to the pumpkin patch and challenge your guy to a pumpkin carving contest. While he's diverted, carve 'will you marry me?' on your pumpkin and present it to him when you're both finished carving. You'll probably win the contest then.
Proposing with extreme sporting. Obviously, this one isn't for everyone, but if you and your guy are super into extreme sports, it's a great way to pop the question. You'll probably need the assistance of your friends or instructors, so make sure they don't give away the game beforehand! Go skydiving with your guy and have your friends spread out a sign below the two of you that asks him to marry you. Go scuba diving and have a waterproof sign already planted down on the ocean floor for your guy to find with you as you're swimming around down there together.
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