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How to Propose to a Woman Who's Already Expecting a Ring

by Jaime Case

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You've been together for four years and your girlfriend has been leaving pictures of engagement rings around the house for the past two. You're finally ready to bite the bullet, but you feel like she'll be expecting any proposal that you concoct. Before you throw up your hands and send her the ring via FedEx, try these creative proposals instead.

Rise and Shine


Plan your next out of town trip with the proposal in mind by booking tickets for flights that leave early in the morning. It's pretty much a given that no one is fully awake at four in the morning, giving you the prime opportunity to pop the question in the boarding area prior to your flight. Offer to grab your girlfriend some breakfast, slipping the ring box into the packaging before handing her the food.

Have Someone Else Do It


Bring back the singing telegram by hiring a service to show up at your fiancée's office or apartment with a song and a ring box. She'll be confused at first until you pop out from around the corner at the last minute. You can also employ this strategy by getting a friend of hers in on the game by proposing during a girl's night or while your girlfriend is having coffee with a friend.

Roller Coaster of Love


The last thing she'll be thinking about while riding a roller coaster is the fact that you might be about to propose to her. Pop the question during the climb and capture her reaction forever on theme park cameras as you begin the descent. Ride the coaster several times before proposing to figure out the when and where of the cameras to ensure that your moment is captured forever.

Tweet It


Get in good with the digital age by proposing via Twitter. Send out a tweet asking your significant other to marry you. Then have friends re-tweet the message until your girlfriend finally notices the message in her feed. Bonus points for including a link to a picture of you on bended knee.

Go With the Everyday


Everyday activities provide the best surprise proposal options. Catch her off guard while she's in the shower, drying her hair, or even cleaning the kitchen floors. Find her during lunch as she chats with her office mates or drop in as she's leaving the gym from a workout. The key is to choose a time when her focus is shifted from love and marriage to the challenges of daily life.

Wait For Her to Do It


This is the lazy man's option, but really, you've waited this long, why not let her carry the burden of figuring out how to propose to you? Start leaving pictures for her around the house and see what happens... you might be surprised to find her on bended knee by your gym locker someday soon.

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