10 Marriage proposal stories

Valentine’s Day is the most popular day of the year for marriage proposals. We talked to dozens of real life couples about the day they got engaged. The stories were varied – from funny to romantic and oftentimes a little bit of both. Here are our 10 favorite marriage proposal stories.

Man proposing at picnic

Colleen and Ross (married 8 years)

Colleen and Ross had been dating for nearly two years and living together for a year, when they decided to get hitched. His proposal was sort of a non-proposal.

From Colleen: “We were at dinner with his parents and he kept looking at me strangely all night. We got home and I asked what was up, and he said he was going to ask me to marry him but thought his
parents would make too big a deal out of it.

I said, ‘Screw that, we should just go to Vegas’ and he asked if I would do that, thinking I wanted a big wedding. I said Hell YES! and we booked it then and there. We flew out exactly 2 weeks
later and got married at the Little White Chapel on the Strip.”

Cherise and Steven (married 5 1/2 years)

Cherise and Steven went through a lot of rough spots in their relationship, but they stuck it out and made it work.

From Cherise: “Steven and I probably broke up five times in our first 9 months of dating. He was always late, loved hanging out with his boys, just didn’t seem to have enough time for me. I told
him that I didn’t think he was in it for the long haul, so it was best to end it for good. So when we broke up for the final time, I thought that was it.

Two days after we split up, I met up with about five or six of my girlfriends at a local bar for my friend Jessica’s birthday. We were kicking back, laughing and having a few drinks, while
listening to some bad karaoke singers.

When I heard, ‘Next up on the stage, Steven.’ I didn’t think twice about it since Steven is a popular name. But when I looked up, I saw MY Steven. He began to belt out, Bryan Adams’ Everything
I do (I Do It For You)
and I was in shock.

At the end of the song, he said into the mic, ‘Cherise, I just wanted you to know that I AM in it for the long haul.’ And there, on the stage in front of everyone, he asked me to marry him.

Apparently, he had been planning this with my friend Jessica for weeks. We got married a few months later and have been very happy for the last five years.”

Melissa and Eric (married 3 years in May)

Melissa and Eric now run a wedding favors website (among other ventures), so it’s no wonder their wedding proposal was so romantic.

From Melissa: “Eric had planned it for like 4 months completely unknown to me, of course. It was on our 3 year anniversary of dating and he took me down to Shelter Island to a restaurant that was
in a hotel (AJ’s Bar and Grill) – great food that overlooked a private beach the resort owned.

So we eat dinner and he is totally smiling at me the entire time and can’t stop giggling, it was too cute! So we finish and he tells me that there was a surprise back at our house and that’s what
he was excited about. Well he had me completely convinced we were going home, so we get in the car after dinner and start driving down the street, when we come to a round about that takes you off
this little island. He keeps going around, doesn’t leave and just returns to the hotel! (That is totally Eric and his “sly” moves.)

So we pull into the parking lot and I am completely confused wondering why we returned and he said we were staying for 3 days! I was so excited because we had never really gone on a trip like that.
Little did I know he had packed my bags, which were hiding in the back seat. We go into the hotel and go straight to the room, we get to the door and he tells me to close my eyes … that’s when I
KNEW IT! And of course I start to tear up as I close my eyes.

He led me into the room. And when I opened my eyes the room was filled with roses and candles and he was on his knee asking me to marry him. It was the best night of my life, the roses even had
little cards in them that read “Will you marry me?” – sweetest thing EVER.”

Click to the next page to read more marriage proposals.


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