He Said, “Yes!”

There are no hard and fast rules for proposals, as long as you come out of it engaged it was a success! Over the years we have talked a lot about proposing to a woman (and we will continue to do so, don’t worry). We wanted to take some time to discuss proposing to a man because in this day and age we see more and more of that!



on a brick path alongside of water with a beautiful city behind the, a woman in a floral dress and heels kneels in front of a man with ring box extended. Tall man in taupe suit with man bun and beard looking down at her. Small dog between them.

As with anyone who is on the verge of proposing, it is vital to determine if this is a course of action that your intended is ready for. You can check the proverbial temperature on that while keeping your secret plans secret…if you are sneaky!

Ask him about future goals that would include a potential spouse. You want to determine if he is interested in being married. The hard part about this is that none of this part is really about you. Some people do not want to get married ever and that is not a reflection on you or even how they feel about you. That doesn’t mean that you can’t have a rich romantic life, and you can even bling it up. There is a difference between never and not right now as well. You need to get the measure of his feelings in that regard.

Ask his friends, if you are close to them. Realize that they may relay information to him, but you can ask them for stories about him or his dreams as they know them.

Use experiences around you! If there is an over-the-top proposal on TV, ask hypothetically what he thinks about that.  “Wow, they put a lot of time into that setup, what would you even think if someone surprised you like that? Would you even like that or something like a quiet dinner?”

We don’t actually encourage you to be duplicitous with your partner, but we know that the surprise is important and it takes effort to maintain.



brown men's hands in front of a suited chest with a stunning men's ring on the ring finger with a large diamond.
Tiffany Men’s Engagement Ring. (Image Source: Tiffany & Co.)

Not all men will want to wear an engagement ring, but some for sure will. Tiffany & Co has launched a new line of men’s engagement rings, because the market for them is growing! The Charles Tiffany setting is named after the founder of the company. This is another area that you will need to check the temperature on. What I would do is save the money that I would put towards the ring and propose with a placeholder. Once you get that Yes!, you can offer either a ring or something else like a vacation or a different piece of jewelry.


PREPARE YOUR MINDTaller blonde man in a white shirt and black pants proposing to a shorter bearded brunette man in a printed top and white pants. They are outdoors in front of an Adirondack chair.

There may be people who question acting against tradition. The real tradition is love and you are grabbing life by the reins. You should be able to do what works best for you and your partner. I 100% believe that it should be between the intended couple, but the reality is that someone is likely to say something and you need to prepare yourself for that. Is that something that you can deal with or will that bother you? Be honest with yourself, because you don’t want that playing in your mind.

Just prepare yourself to potentially be asked and have an answer at the ready. Live out loud and love fiercely! It’s a beautiful thing to have a love so strong that you want to spend the rest of your life with that person. Just focus on the love and your future.



The longer that you plan and scheme the more likely it is that the secret will come out. Keep it to yourself until you are at a place where you need to bring in backup and keep it as close to the vest as possible. That is not really only relevant when proposing to a man, but for any surprise proposal. Surprises are quickly spoiled, so unless you need a whole crew for a dance mob or a full-on party, keep it close.


  1. Make sure you know how he feels about marriage.
  2. Make sure you know how he would feel about being proposed to.
  3. Plan something personal and meaningful for both of you.
  4. Determine how you want to approach the engagement ring.
  5. Prepare your answers to people questioning your decisions. It’s not really for them, but to give yourself the freedom to answer and divest yourself of that concern.
  6. Don’t spend months preparing, the longer you wait the bigger the chance for a spoiled surprise.
  7. Enjoy the moment, we hope you get that big YES that you are dreaming of.
  8. When you DO get the Yes!, come tell us all about it!




Brushed Beveled Edge Wedding Ring in 14k White and Rose Gold
Brushed Beveled Edge Ring in 14k White and Rose Gold from Blue Nile


<center>14k White Gold Men's Ring with Center Diamond and 2 Accent Diamonds from Whiteflash</center>
14k White Gold Men’s Ring with Center Diamond and 2 Accent Diamonds from Whiteflash

Have you proposed to a man? Are you a man that has been proposed to? We would love to hear your stories! Please share with us in the comments!

Written by Kayti Kawachi

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