When and How to Propose

Women wait all of their lives for the love of their life to win their hearts and whisk them away.  They dream of the perfect proposal: a dinner at a fancy Italian restaurant with a diamond ring hidden in the dessert, or at a family event in front of her still-single frienemie from college. 

Whatever the case, know that she has been thinking about this moment since she was a child.  There is a lot of pressure riding on you to make it perfect, and you should stop short of nothing to make it one of the most memorable days of her life.

Step 1: Pick the Right Time

First, you must decide when you are going to propose.  Timing is everything when it comes to asking her for her hand in marriage.  You have to be certain that you are willing to spend the rest of your life with her; if you’re not sure, then don’t propose.

Step 2: Make Sure You Are Truly in Love

Are you truly in love?  Ideally, you should have dated her for over a year before even thinking about getting engaged.  This is a lifetime commitment and should not be based completely on emotion.  Take some time to deeply reflect upon your life goals and what you are personally looking for in your future.  If you can’t picture it without her, then that’s a good sign to get engaged.

Step 3: Check Your Finances

Make sure you both are stable enough to get married.  Are you still in school, or trying to pay off debt?  Is she taking care of her elderly parents, or (worse) are you still living with yours?  Preferably you should be out of school and have a stable career with your finances and long term goals in order before popping the big question.

Step 4: Decide How You Will Propose

Once you are certain you are ready to ask her to get married, you need to choose how you are going to do it.  If you’ve been together long enough, she has probably dropped a few big hints.  Be careful to match the proposal to her personality, not yours.  You may love the Saints, but unless she’s a huge fan too, be aware that proposing to her at a Saints game on the big screen is your idea of romance, not hers. 

Avoid doing anything too cliché or too dangerous.  Asking her to marry you a mile up in the air right before you jump out of a plane to go skydiving may sound exciting, but if she’s screaming bloody murder as you fall out of the plane trying to get on one knee, you will regret it for a long time.

Step 5: Decide Whether You Will Propose in Private or in Public

Think about who she is and whether she would most enjoy a big announcement or a private proposal.  For instance, if she’s particularly shy you should avoid proposing in a grandiose manner.  You don’t want her to have a panic attack when she sees a giant ‘Will You Marry Me?’ sign in your local concert venue in front of 60,000 people.

In most cases, it’s usually better to have an intimate setting where she will give you a truthful answer.  If you ask her in front of other people, whether it’s live onstage at a rock show or just in front of your Mom and Pops, she will feel a lot of pressure on her to give a positive answer, and she may resent this if she still hasn’t made up her mind.  However, you should propose with some flare so she can brag about it to her friends.

Final Tips on Proposing

If you want to be traditional, ask her father for permission before proposing. 

Make sure too that however you decide to propose, the best advice is to pick a venue that is special to her.  Did she have a favorite park she visited as a child, or did her dad take her sailing when she was younger? 

It’s fairly easy to book a location to propose as most business owners are willing to help you out.  If you tip them they may be willing to close the zoo tiger house for 30 minutes, or set out a special romantic table for you at her favorite beach cafe. One word of advice: tip well!

Once you choose the right time and place, you are ready to propose.  The rest is up to you!