I Proposed to My Fiancée Twice; the Second Time Was Better

I love my fiancée so much that I proposed to her twice.

It wasn’t because I didn’t believe my lover — who is admittedly far out of my league — the first time she said yes, nor was it my pesky perfectionism rearing its demanding head because not every detail went according to plan.

Rather, certain aspects of our engagement didn’t quite meet our expectations.

There are a lot of things my fiancée and I fondly reflect on when we talk about the day we got engaged — the location in her hometown, New York City; the perfect fit of her rose-gold ring from a nearby jeweler; the violinist who flawlessly played her favorite songs.

However, at the same time, it felt sabotaged by some people in our lives who were emotionally standing in our way instead of celebrating us. I was also at the pinnacle of my unhealthiest self, both mentally and physically.

Seeing the pain behind my eyes while looking at the photographs from that otherwise special day eventually became too much to bear.

As the weeks passed, I kept feeling that we deserved another special day, one completely focused on our love, without a damper from self-consciousness or unsupportive connections.

So, I planned a second proposal about two years after the first.

This time around, the proposal day was even more magical

I felt inspired as I planned another proposal to my fiancée.

In the two or so years since the first engagement, we’d eliminated a lot of the stressors that had been holding us back. For one, I’d lost a significant amount of weight and was mentally in a much better place.

Now, I had a chance to profess my undying love for the woman of my dreams again, this time unbothered by others’ opinions and with the renewed confidence that comes with drastically improved health.

Instead of heading back to NYC, I set my sights on proposing during the Disneyland trip we’d been planning.

She had no idea what was to come as we drove to Anaheim, California, with a bubbly Disney playlist serving as the soundtrack to our adventure.

Within the magical confines of Main Street, USA, I got down on one knee and renewed my commitment to the same loving promises I shared the first time around.

I expressed my excitement for our coming marriage, and once more promised her forever. Again, she said yes.

Instead of buying another engagement ring for the occasion, I surprised her with a piece of jewelry that matched the ring she already had.

Then, we headed to the Plaza Inn for a vegan meal surrounded by many of my fiancée’s favorite Disney characters. It felt magical.

A proposal doesn’t need to be a disaster to get a do-over

A second proposal wasn’t necessary, but it was worth it in every way to see the bliss on my fiancée’s face as we created another beautiful moment together.

Now, we have even more wonderful memories to reflect on, and the best part is, the day was entirely about us and our love.

Truthfully, I recommend a second proposal to anyone who felt their first attempt wasn’t as magical as they deserved.

Whether you lost the ring, forgot to say the best parts of your speech, or just had an even better idea, a second proposal could show your lover that you’re recommitting to them in a romantic and innovative way.

Maybe it’s unconventional, but we live in a time when breaking free from tradition is becoming the norm, whether it’s as simple as living together before marriage or as milquetoast as having food trucks at a wedding.

So why not propose to the love of your life a second time? It’s a way to remind them how much you want to marry them — and it could be the start of another great chapter.