The Best, Most Creative Ways to Propose to Someone

With Valentine’s Day a week away, I wanted to address some of the questions people ask me about marriage proposals. This is written from the perspective of a man proposing to a woman but it applies to either sex asking or receiving. (This was first published on, and if you like this, would you share it from that link?)

Do you want to propose to your sweetheart?  If you are not ready to propose or accept a proposal, check out my other article on – “Asking Yourself, “Should I Get Married? Here’s How to Know For Sure.”

If you do want to propose, you probably want your proposal to be special.

Have you watched some YouTube videos of proposals that are amazing, fun, outrageous, sometimes involving tens or hundreds of people or some elaborate scheme that is carefully choreographed? CAUTION: Do not compare what you do to these videos! There are thousands of proposals or maybe hundreds of thousands for every video posted. And most of the proposals are special because the proposal was tailored to the person receiving it

You want your proposal to be special – but how do you make it creative? Creative doesn’t mean some off-the-chart proposal that will be written up in the Guinness Book of Records.

You absolutely can be creative when proposing.

Why? Because you can think of something special that your partner would love that is personal to only them and would make your proposal an event they will never forget. unhide

Here’s 3 ways to make your proposal special for the person you want to marry you!

  1. Make it a unique experience just for her or him based on what you know about what they love.
    • Consider proposing when you are doing something fun that she enjoys – like going bike riding, skiing, on a picnic, her favorite movie marathon with friends, at a concert,  or having a picnic – and she would never expect a proposal.
    • You can use a meaningful theme for the ring (like Disney) or a special stone instead of a diamond. You can have it be very private or involve friends and family, be elegant or casual based on what they like.
    • Include her favorite flowers, a song she loves, at her favorite restaurant, whatever she loves. The point is to make the proposal unique to her (or him) and heartful. It can become a strong foundation for your future.
  2. Make your proposal part of celebrating a holiday, birthday or special occasion like a romantic dinner or on a cruise.
    • Valentine’s Day, birthdays, holidays and romantic vacations are a perfect time for a proposal.  If you know she’s hoping for a proposal, and if you are ready to commit, then go for it. (Don’t propose just because you think or know they expect it. A proposal is your offering of love forever so do not do it to please your partner.)
    • A proposal on a special day can still be a surprise because she wasn’t expecting it exactly the way you did it, plus she will not disappointed coming home empty-handed from that romantic event. You gave it to her when she wanted it.
  3. Surprise! Make it unexpected.
    • Give her that personalized surprising proposal. If she would want something else, then keep reading to give her that personalized surprise proposal.
    • Don’t make it too surprising that there is a high risk of unintended consequences like buying the ring in a cupcake and she breaks her tooth on it when she bites into it! It could be a very funny story in the future depending on her sense of humor.

Here’s an example of a romantic proposal full or surprises that my friend, Lila, shared. This has all the elements I mentioned. Romance and the element of surprise kept building suspense.

“In the late afternoon, my boyfriend, Steve, told me to put my best dress on. When I got dressed, I came out of the bathroom and he had left a card on the bed that sent me to my office to get my purse. The next note, in my purse, sent me downstairs to get my coat. The note in my coat pocket had me sit by the living room window to wait for my ride. Fifteen minutes later a long black limousine pulled up and the driver came to the door.

I was taken to a lovely restaurant known for delicious food and a fantastic view.  The maître de was expecting me and immediately seated me at a table by the window. I was served a glass of my favorite wine, then the maître de brought me a beautiful bouquet of long-stemmed red roses.

As I finished my wine, a card was delivered to me that said, “Your Prince Charming Awaits.”  Steve, a handsome man who carried himself like James Bond, made an entrance wearing a beautiful black tux and looking very handsome. Champagne was served then our favorite song was played.

By now, everyone in the restaurant knew something romantic was happening, even me!  At this point, I was thinking that he might propose… and then he did.  This was the most romantic proposal I have ever received (out of four proposals).

Wow, this proposal had everything in it!  It is romantic, special, personal and full of surprises.

Guess what? She did not accept. When he asked, she could not say “yes.” Why? He was an alcoholic. So you can see the perfect proposal is no guarantee. Sometimes, a proposal forces the two of you to answer the question “Is this someone I want to spend the rest of my life, no matter what happens?” If the answer is no, then the answer to the proposal should be “no.”

Creative for creative sake doesn’t make it truly personal to her so be sure that whatever you are creating will touch her heart and make her feel special.

Here are two videos of creative proposals: (Do you agree?)

  • In this video, a couple went on a walk in the woods where they discovered a wooden box buried under a rock that he had planted in advance. At 6:15 they find the box. You can start here or start at the beginning.  She is in total shock by the end. What’s unusual is that she did the video of him uncovering the box so they have a recording.
  • In this video, the groom (Isaac) involved so many family and friends who helped him orchestrate this amazing proposal. I cry at commercials and this video definitely moved me to tears. You can see that their friends and family helped put on an amazing “show” which demonstrated how they are all supporting this couple’s union. Every time I watch this, I am touched by the support, love, and joy everyone gave to Isaac and his fiancé by being a part of this proposal.

These creative proposals are definitely memorable. Both of these are great examples, not because they were clever (and they were), but because they were made with love and commitment. The video above with Isaac gets points because he made his proposal personal and included their family and friends not because he got people to dance in the street.  And the effort to rehearse for that performance showed the love and affection family and friends had to make this special.

When I asked my friends to share their ideas for a creative proposal, several shared that their husband’s proposal was not creative but it was from the heart and was “sweet.” Each of these women spoke about how their husbands expressed his love, often in a way that he normally wouldn’t, so that his declaration of love was precious to them.

My husband’s proposal is an example of this….He asked a clerk at a store “Will you help my fiancé?”  I looked at him and said “Fiancé?!” He looked at me like he didn’t understand what I was saying. He didn’t realize he had called me his fiancé.  He said it unconsciously – just saying how he felt about me. I wasn’t expecting a proposal and it wasn’t actually a proposal but it was a declaration of love that showed me he truly saw me as his partner for life.

The most important thing is that you know this person is a good partner for you. You can be yourself with them and they can be authentic and real with you. You trust them and share values with them. Even if they lost their money, their hair, their figure, or their fancy car, you would still love them!

The perfect proposal doesn’t equal a perfect marriage so be sure you are ready to commit, no matter which side of the proposal you are on. And also recognize that even when you meet a partner who is perfect for you or even a soul mate, you must still practice relationship and communication habits that sustain love.  Lasting love isn’t guaranteed when you propose, you must build it every day.

I wish you lasting love!

This New Normal of Uncertainty & How to Relax

 Are all the changes you are dealing with in this "new reality" having you more reactive that you normally are?  Are your relationships with family, friends and work colleagues being impacted?  Are you more emotional? I have always cried when I read or...

Give yourself “Total Permission to Say ‘Yes’ to Life” as a Woman

Have you heard this song by Wahkeena Sitka – called “Total Permission to Say ‘Yes’ to Life?” I invite you to listen to 3:25 minutes of the feminine desires of the heart that she is expressing with such joy! Wow, when I heard this song, it...

What Kind of Relationship Do You Want to Create?

We often sabotage our intentions because we have "survival habits" from the past that thwart our intentions.  Why do these habits of the past block us from having the relationships we want?  Because we are not aware of what we are really thinking, feeling,...

7 Terrible Reasons To Get Married (That Are More Common Than You’d Think!)

You want to get married.  The big question is WHY? The following 7 reasons are all good reasons to get married: You can be yourself when you are with him and he loves you just the way you are and the way you are not and you feel the same about him. You don’t plan...

11 Things I Would Never Do as a Stepmom of Teens and Young Adults

I married for the first time at age 49. My 5 step kids were 15-24 when we married. I was lucky when I was growing up. My mom was very loving and kind and everyone loved her.  I was heartbroken when she died a week after our wedding because my stepchildren didn’t...

5 Things That Turn Guys Off (That Women Have No Clue About)

I asked several male friends over 40 years old, “What turns you off that women have no clue about?” You probably have heard at least some of these turn-offs from men; however, knowing these are issues for men may not have motivated you to stop doing them. Maybe this...

Did you miss your chance to celebrate “National Blame Someone Else” Day?

The first 'Friday the 13th' of every year is "National Blame Someone Else Day.   Did you celebrate?  This year it was August 13, 2021. It's been described as the compulsive liar's dream day!  It's the one day when you (supposedly) have permission for a full...

Is the Person You Are Dating a “Keeper”?

 What should you look for when you are moving from dating into a more committed relationship? If you are dating for fun, then as long as you are having fun, it’s all good. But what if you want to get married, build a partnership, and maybe start a family? Here are...

Create a Fresh Restart (If You Are Willing to Let Go of The Familiar)

There are several times during the year when there can be a recognition that this is a good time to make a change or start something new.  For example, the beginning of the year is seen as a great time to declare a break from the past.   Other times include...

Imagine You Could Listen with Total Love

I hope by reading this you can make this upcoming Mother’s Day a happier day for you (whether you’re a mom or a child) …  My mom was an incredible woman.  She was loving and when I was a teen, all my friends loved coming to my house and sitting at the kitchen...