2) NOT My Finest Moment

It was NOT my finest moment! Sure, I started out with a plan. My proposal was going to be romantic, beautiful, and perfect. But my plan got foiled – not once but three times! In the end, I had her staring at the ceiling, saying, "are you sure?" But let’s not get ahead of ourselves.

Shannon and I have been dating for nearly five years. I guess it’s hard to call it "dating" when you’ve been living together for over three years, but for lack of a better term – we’re dating. It had become painfully obvious to everyone but me that it was time to take next step forward. To me, getting married was not a step – it was a running leap from the roof of one skyscraper to the next. But, I conquered my commitment phobia, and was committed to spending the rest of my life with an amazing woman.

As her 30th birthday approached, I decided this was a perfect opportunity to pop the question. I reserved a room at a nice hotel. I made reservations at a top-notch restaurant that we’ve been meaning

to try. I made plans to get the ring.

It was Thursday (her birthday) and a coworker of mine helped me pick out and purchase the ring. My plan was to throw her off a little and do nothing for her actual birthday. We had plans to go out with her friends on Friday, and she knew I had plans on Saturday. So I was safe until…

As soon as my coworker found out that we were going to have dinner with her friends, she said that I MUST pop the question before that. "This is what women want," she tells me. "They want to show off the rock as soon as possible to as many people as possible!" But I have plans! Foiled #1.

Okay, I’ll do it tonight. It wont be what I planned, but it will work. I’ve got the ring in my pocket. I’ll take her out to eat, and do it at the restaurant. Maybe I’ll have the waiter slip in her drink. I’m going to have to improvise a little.

I’m driving home, and I’m nervous! Im really going to do this. I’m doing it tonight. As I arrived home I see a familiar car in my driveway. Her parents are here "surprise" to take her out to dinner. Foiled again.

I’m not going to do this in front of her mom, dad, sister, and grandmother. While that may be a nice sentiment, I know Shannon, and she would not want that. I don’t recall what I had for dinner; I

just remember that I couldn’t taste a bite. What am I going to do now? All right, I guess Ill have to do it when we get home. I’ll take her out for ice cream. That could work.

So we all drive back to our house, and I figure her parents will leave shortly – they have over an hour drive home and its already 9:00. Except they brought a pie, and want to light birthday candles, and sing "Happy Birthday." Third time Foiled!

By 10:00, Shannons family has finally departed, and before I can say anything, Shannon has put on her pajamas, and is headed to sleep. What the heck am I going to do? I have to do this tonight. I’m running out of time. I’ve run out of options to make it romantic. There is no way its going to be beautiful. It’s anything but perfect. But I’ve run out of options. It’s time to throw the "Hail Mary!"

"Don’t you want my present," I ask. She seems unsure of herself, but I convince her that it will be worthwhile. The ring is in the bedroom in my sock drawer (it seemed like a good place at the time). I need to get her out of the bedroom, so I can have some resemblance of a nice moment. So I bring her to the living room of our one bedroom apartment and tell her to stare at the ceilingit was the best I could do. I run back to the bedroom and fumble around in the sock drawer. After what seemed like an eternity, I find the ring. Meanwhile Shannon is asking if she can stop staring at the ceiling, she tired of seeing cobwebs and spiders. "NO!," I yell.

So there she is, the love of my life in her flannel pajamas, looking up at the ceiling. This is the woman I’m going to propose to. I sneak behind her, get on one knee, grab her hand as she spins around

kneeing me in the face. I really don’t recall what I said, and thankfully neither does she, but ring in hand I’m pretty certain I asked her to marry me. I do remember her response, "Are you sure?"

Am I sure? Am I sure? You have no idea what I’ve been through! I’m sure as sure!

Thankfully, "are you sure" was soon turned around with a big fat "YES!" It just took a few moments for her to get over the shock. We were married this September, and even though it wasn’t my finest moment – it was very much one of my finest moments.


Proposal Story By:

Ken Gutman

Oakland, CA


The founder and president of Diamond Cutters International, is one of the worlds top diamond experts, as well as a three-time Guinness Book record holder in jewelry design.
Fred The Diamond Guy
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