Once you have decided that the person you are dating is “the one”, then it’s time to propose (men, I’m looking at you). Engagement is the last DTR a dating couple will ever have; it effectively ends the dating relationship. The couple has decided that they are ready to promise their love to each other without condition or expectation.

Of course, getting engaged is one of the most highly anticipated moments for any man or woman. It should be something that happens once in a lifetime and becomes a story that the couple can tell for years to come.

I heard a story of a man who saw his girlfriend off to a summer abroad in France. Before she left, he gave her a letter for each week she was there. Each one had to be opened in a certain place at a certain time. Towards the end of her summer in Paris, one of her last letters said, “Eiffel Tower 3pm”. While atop the Eiffel Tower she read one of the most meaningful letters she had ever received from her boyfriend. And the final line of the letter said, “turn around.” She clasped her hands over her mouth and turned around and there he was. On one knee. Asking her to be his wife. Atop the Eiffel Tower.

Not bad.

On the other hand, some guys just don’t seem to understand that most women don’t daydream about being proposed to at a sporting event. . .

Remember, guys, your method is your message and there is no better demonstration of what your message is than the way you choose to propose. Although this will not be an exhaustive list or “how-to” session on asking a woman to marry you, there are certainly a few things that you need to know before you proceed.

  • Get her best friends involved. This is the single best piece of information I can give you. They should be your number one resource on helping you organize the event and keeping it a surprise. They will also let you know if what you are planning will sweep her off her feet or cause her to slap you in the face. Give them plenty of advance notice so they can make plans to be there and celebrate with her. As much as they can and want to be involved, welcome it! Major points off if you don’t do this.
  • Make the proposal unique and special. Do not copy another person’s proposal. Don’t even steal specific parts of another person’s proposal. Instead, make it both unique and special by paying attention to the significant events, places, themes, etc. of your dating relationship and develop a proposal that incorporates them all into one.
  • Speak her language. Guys, don’t propose the way you want to propose. Instead, know your girlfriend well enough to be able to decide whether or not she would like to be proposed to at a baseball game. Even if that has been your dream ever since you were 9, don’t do it. Propose to her when, where, and how she’s been dreaming since she was 9. The closer you can get to her dreams, the more swept off of her feet she will feel.
  • Spare no expense.  Hopefully, you’ll only ask this one woman to marry you once in your (and her) lifetime. Don’t be cheap. Don’t be rushed. Don’t cut corners. Go all out. Neither of you will have the chance to do this again. [You should also plan an after-party where everyone can meet the newly engaged bride-to-be. Invite her family, your family, all of her friends and anyone else you’d like].
  • Bottom line:  give her a story she wants to tell!  Whatever you choose to do, remember that every time from then on when someone asks her how her husband proposed to her, she will have to tell the story. It’s a story that she will tell for the rest of her life. Give her a story that she will never tire of telling. Give her a story that will inspire other men who hear it to do it right as well. Give her a story that makes her light up when she tells it – even if she tells it 10 times a day. Give her a story that reminds her how much you love her.

We’ve almost reached the end of the blook! The final chapters will focus on what to do while engaged (chapter 4.5), the wedding itself (chapter 4.6), and then some concluding remarks.


What is the best proposal story that you have ever heard?

Women, are there other things that belong on this list?