“What do you mean you’re not sure about proposing to your fiancée?”

“I’m serious. I’m not sure she’ll say yes if I propose.”

“But you’ve been seeing each other five years now, you’re sharing toothbrushes and working out in the same gym together. Last time I checked, she was still wearing that necklace you gave her.”

“Yes, well, it’s complicated. Now that I want to give her a ring, things seem a bit different. Like she’s not nagging me anymore about commitment and stuff. I don’t know, my gut instinct tells me I should probably wait until I’m absolutely certain she’ll say yes.”

Some men have a sense of insecurity about proposing to their fiancée. In the beginning they freak out when their sweetheart talks about buying a house and raising kids, and then when she actually stops talking about their future together, the same scared men are worried that maybe the love’s flown out of the window. This time they’re still scared but for a different reason: they are intrigued by their girlfriend’s lack of interest, and the funny part is, she’s spending more time on her own rather than with him.

What’s happening? Your guess is as good as ours. Either she got tired asking (yes, women do get tired of asking for an engagement) and has set her sights on someone else or she got warned by her married friends that marriage, after all, isn’t a bed of roses. And the thought of giving up on certain freedoms has made her re-think her situation regarding remaining single or getting hitched.

It could also be a ploy on her part to get her man to propose. Maybe she received some valuable advice about how to snare him into finally popping the question by her display of indifference. We all know women can be such catty creatures; there are those who’ll try every trick in the book to stalk their prey and then set the trap. History is replete with examples; so is Hollywood.

Proposing to Your Fiancée: Be Creative

We’ve all felt that warm glow when a dear friend or relative relates how her significant other proposed. While some follow the standard way of proposing – dinner followed by the small satin box and then the $64 question, some have chosen to go the creative route, so that the proposal comes as a total surprise.

We’ll narrate a few examples and maybe your imagination will go wild:

• Picking a special occasion to propose – to make special occasions more special, men choose to propose to their sweethearts during Christmas, Valentine’s Day, her birthday, Easter, Independence Day or Labor Day (to retain the humor).
• Going on a trip – some clever men will go on a trip with their girlfriends and put the engagement ring in their suitcase. When they find it, that’s when they pop the question.
• Renting a blimp – a fellow invites his girl to a park and then they sit on a bench where she can see the blimp clearly going by with the floating ribbon saying “Kate, my love, will you be mine forever?”
• Dining first class – some men are also very naughty. They invite their girlfriends for a heavy duty evening, requesting them to wear something really elegant and formal, sort of making them believe that “tonite’s da night.” They choose a very expensive restaurant, order a pricey bottle of champagne, have the most expensive item on the menu, and then go dancing afterwards. BUT – it’s just a dinner, and there is no proposal coming. They just mislead their ladies into thinking that they’re about to propose but don’t actually pop the question. Two weeks later, they call and say, “remember that night we went out and painted the town red? I forgot to ask you. Will you be my wife?”
• Serenading – one time, a colleague was taken by surprise and was slightly embarrassed when a young man with a guitar came to the office and started singing to her. Everyone stopped working and stared at their direction, and our colleague was blushing with no idea why this man was singing to her. After he sang, the singer explained he had been commissioned by her boyfriend to sing her favorite song. Then he told her that he gave her email address to someone who was supposed to confirm his next “singing engagement” so he requested her to check her email. When she did, there was an email from her boyfriend asking for her hand in marriage. Our colleague wept tears of joy, because she told us later that she didn’t think he was the marrying type.

So you see, there are a hundred and one ways to go about proposing to your fiancée. You can even propose underwater with your oxygen tanks if both of you are scuba divers, or you can take her bungee jumping and pick out a spot to land and then when she lands, she sees the question. Your imagination will take you places.

Proposing to your Fiancée: Don’t Forget the Diamond Ring…and the Other Stuff

Like most undertakings, you need to do a bit of research. You need to get an engagement ring but before you spend money on a diamond, make sure she does like diamonds. Not all women believe these stones make the best of friends. Nor do they all like white gold or silver.

An alternative – if you’re not sure – is to go shopping for the ring together after you propose. If she’s very particular in her tastes, that would save you the trouble of having to return the ring to the jeweler. Know her ring size, and do take out insurance especially if you’re spending a handsome amount for it. Rings always get misplaced.

When the ring issue is resolved, you’ll have to pick the right words to craft your proposal. Maybe you’re an incurable romantic and want to write your proposal in the form of a poem. Or you can sing to her. Pick a moment when you’re both relaxed and not stressed from the demands of your work schedule – during a candlelight dinner – a vacation – a long walk in the park – Sunday brunch.

Asking a third party to do the proposing to your fiancée on your behalf is probably not the best idea. Some women may not mind and may actually find it hilarious while some women think that a proposal is a very personal thing between two people. Women can get offended when this basic etiquette is overlooked. Think twice about asking someone else to propose on your behalf. It might backfire. If you’re shy or unsure about popping the question, wait until you’ve built some confidence. Or wait until the telltale signs indicate that she’s ready to say… Yes to your proposal!