How to Propose to Your Boyfriend

• by Tracy C.
• Also try: How to Propose

• Mahalo Daily: How to Propose Properly

Introduction

• In the olden days, women were "allowed" (in some cases, as sworn into Parliamentary law) to ask a man to marry on February 29 (only during leap years). Those days have waned, however, as now any day is an appropriate one to pop the question to your unsuspecting boyfriend. With a little advance planning, you can concoct the perfect proposal, one that will have him answering in the affirmative.

Step 1: Get a Sense of His Ideas

Do you see the two of you growing old together? (Creative Commons photo by Lisa Lamb)

• You two have been together for years and marriage doesn't seem out of the question. But do you know his true feelings about proposing?

The Dos and Don'ts of Proposing to Him

• Do propose if you think he will be impressed by your grand gesture.
• Don't propose if you think he may feel threatened.
• Do propose if certain circumstances might make him wonder how you truly feel about him:
  • • Has he tried proposing in the past and you have been unsure?
    • Will this be a second marriage for you?
    • Have you been unable to express yourself in the relationship?
    • Have you had wavering thoughts on marriage itself and want him to be sure you think it's a good idea?
    • Was he attracted to you for your independence and non-traditional ideas in the first place?
    • Are there children involved who might make it hard for him to know if you want to enter into a new family?
• Don't propose in front of family or friends unless you know it is what he would want. If you are in the least bit unsure of how he will react, it's best to make this special proposal in private.
• Do craft a proposal tailored to his personality, and not yours.
• Don't be surprised if he is a little taken aback or feels you may have stolen his thunder.

Step 2: Decide on a Symbol

Some couples get matching engagement rings. (Creative Commons photo by Pixel Drip)

• Will you find an engagement ring or other appropriate symbol?

1. The ring issue can be a tad tricky. If he wasn't planning on an engagement, you can't expect him to buy you a ring.
2. If you are certain he had planned to pop the question (eventually) himself, it could be appropriate to ask him to marry you and then suggest that the two of you go to pick out an engagement ring together or choose wedding bands together.
3. Will you give him a ring as part of your proposal? If so, be sure to figure out what style he might like and what his ring size is. Subtlety in this venture is key.
4. You could get matching rings to symbolize your engagement.
5. Most women have some input on their rings anyway; why not pick yours out yourself?
6. Or, you could forego the ring tradition altogether and select an appropriate gift that he will truly appreciate.

Step 3: Make a Plan

Maybe his (other) best pal can deliver your message? (Creative Commons photo by Bala)

• Every good proposal requires advance planning.

1. See Mahalo's guides to How to Propose and How to Plan a Destination Proposal for extensive proposal ideas.
2. Decide whether or not you will contact his parents for permission, or their blessing. If you think they might balk at your decision, be sure you have the confidence to go forward.
3. Remember that this proposal is now about him, not you. While you may have imagined a horse-drawn carriage when fantasizing about your perfect proposal back in kindergarten, he is less likely to share this dream.
4. For the publicly romantic, you could try, as Shannon Thomas did, publishing your proposal and then finding the right way for him to stumble upon it.
5. For private types, try cooking several of his favorite items and then serve up your proposal as dessert. But not in the dessert—this is one of the most common proposal mistakes, sometimes accompanied by a trip to the emergency room.
6. For more private proposal ideas, see The Knot's suggestions.

Step 4: Ask Away!

• It's finally time to pop the question.

1. Getting down on one knee is a charming gesture, regardless of gender.
2. Tell him why you want to marry him. Blurting out a hurried "Willyoumarryme" will ruin the significance of the moment. Take the time to write out a few sentences about why you see the two of you growing old together.
3. You may also want to address why you're asking him instead of the other way around. "We've always had a non-traditional relationship, and I thought this was the best way to enter into marriage," or "Sometimes I don't know if you realize how much you mean to me," etc.
4. And no, "I never thought you'd get around to doing this, so I took matters into my own hands" is probably not what he wants to hear.

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Resources for How to Propose to Your Boyfriend

• The Knot: How to Ask Him
• The Knot: Proposing to Him: 6 Perfectly Private Ideas
• eHow: How to Propose Marriage to a Man
• Real Simple: A Real Simple Marriage Proposal
• The Knot: How to Propose
• Wedding Channel: Presenting the Ring

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