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How To Overcome a Proposal Which Epically Failed…Twice!

The time of year during which the most marriage proposals are made is Thanksgiving to Valentine’s Day…or in the case of 2024, through Leap Day, February 29, when women propose to men. The following blog post is about one man’s persistence in proposing…and the outcome of his efforts!

man holds engagement ring behind his back

Hey, John!

HELP! I have tried to propose twice to my girlfriend, Kaylee, but each time was an epic fail. The first time, I took her on a picnic to our favorite park where I intended to propose. Unfortunately, a swarm of incredibly angry bees interrupted our romantic picnic and chased us out of the park!

Last Saturday, I drove us down to the beach at Cape Mears. When she wasn’t  looking, I wrote, “Will You Marry Me?” in the wet sand. Unfortunately, the waves washed it away before I could get her to turn and look.

I really want to marry Kaylee! She is “the one!” Should I be persistent and try to propose again or just give up?

—Dale, Feeling Defeated in Dallas

LOTR Elven engagement ring MetalWendler
sappphire and diamond wedding engagement ring

Hey, Dale!

Don’t give up! You can do this! Remember: The third time is the charm! 

At least that’s what Michael Greene found.

He persisted through multiple tries to pop the question to the same woman…and finally succeeded!

You will too!

Proposal Attempt #1: New Year’s Eve, 2021

Michael Greene planned out all the details.

He bought the ring. 

Yes, it came in a velvet bag instead of a box which wasn’t ideal but there was a box inventory shortage at the time so he was grateful to have what he had. (We’ll get back to the bag tomorrow.)

He planned a quiet evening playing board games with his beloved, Tomika Anderson. And then the wheels came off the bus: When he lost (badly) in Monopoly, he just didn’t feel like proposing.

So, he didn’t.

Happy New Year 2022
sad stick figure of a person

Proposal Attempt #2: New Year’s Day 2022

Setting the mood for a proposal is integral to getting a positive response from your partner. Michael forgot this basic rule.

In a rush to propose, he rushed into the bathroom as she was stepping out of the shower. With her hair half wet and half dry, he pulled the engagement ring out of the aforementioned velvet bag with a smile…and was greeted by a question he didn’t want to hear.

“Are you serious?” Tomika asked.

On the upside, she tried the ring on.

On the downside, she tried to take it off the next day and found that it was stuck.

Really stuck. Really, really stuck.

The ring would not come off her finger with butter.

The ring would not come off her finger with soap.

Which is how they ended up at the fire department.

One of the firefighters cut the ring off her finger. They were able to retain the diamond for which they later selected a new band.

And so ends Proposal Attempt #2.

red firefighter's hat
halo engagement ring

Proposal Attempt #3: Valentine’s Day, 2022

Tomika asked him for a proposal do-over and he complied in style. This proposal was utterly flawless!

After making a reservation at her favorite restaurant, he hired a limo, a make-up artist, a red carpet, and a private suite at the restaurant. In a suite bedecked with more romantic roses that she could count, Michael proposed.

And Tomika said, “Yes!”

On March 4, 2023, they married in the Turks and Caicos.

By being persistent and not giving up, Michael won the heart of his lady love.

If you’d like help planning your proposal at Ainsworth House & Gardens, reach out to us. We’d be happy to help you prove that the third time is the charm!

Your friend in the wedding business,

John Shyne



Images courtesy of

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illustration of man proposing to woman with wedding ring
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