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Help Me Think of The Perfect Proposal!

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Calling all ladies and gentlemen!  There is a man in dire need of advice and I cannot handle this incredibly romantic and huge request all on my own! So read on and help a brother come up with the PERFECT PROPOSAL for his girlfriend. All together now say...aaaaw!

Dear Jeiry,

So after leading a tumultuous love life of serial monogamy I've finally found the one. Well actually, I guess I should say found her again. See, we actually met two years ago in Los Angeles. We dated a couple of times before she shut me down to focus on her studies. Yeah, I got dumped for some books. Well now she's a Ph.D who got back in touch with me when she moved back east a few months ago. I'm no slouch myself. I'll be graduating law school in 2011. The same chemistry from two years ago was still there and we've been on straight course towards marriage ever since. My problem is that a big part of my surprise for the proposal got ruined. One of my more socially handicapped friends basically blurted out to her that if I ever told her that I planned to take her on a trip to Puerto Rico (where she was born) that it would of course be accompanied with a proposal. As you can all guess, we had booked such a trip just a couple of days before he opened his big mouth. She tried to play it off, but it was obvious to everyone that she knows I am going to ask her and she knows it is going to be during that trip. It also doesn't hurt that we've been ring shopping for the last month and will likely buy one this weekend. Our trip is the first week of March. I am trying to salvage some bit of surprise in the presentation of the ring. I need help coming up with something that will make up for the ruined surprise. We'll be in Puerto Rico for a week in March. Can you or your readers offer any suggestions?

Sincerely,

Proposed Ideas

 

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Gonzo  - A Suggestion for a Proposal   |2010-02-06 22:49:07
1st I'd like to say, Kudos for getting your education first before taking the big leap. Good call! But on to the situation at hand: The Proposal.
When I proposed to my wife it was very simple and non conventional... I proposed in bed...no ring! Yeah, lame-o...but she didn't care. The sentiment was worth the price of the ring. The point: Be creative. Make it memorable, make it heartfelt, make it honest. Where you do it and how you do it is only limited by your imagination. At dinner, on horseback, at el morro, in el yunque in the middle of the forrest... Don't put it in her food! (Too many women have busted teeth and have chooked from food proposals) Good luck buddy. Let us know how it goes!
Timothy  - Viejo San Juan   |2010-02-03 17:48:11
I'll assume you're visiting San Juan. In Viejo San Juan, there are lots of restaurants. Also, there's a nice little plaza full of birds (read pigeons) at the corner of Calle San Francisco y Calle San Jose. My favorite spots are at the top of the hill past Calle San Sebastian and all the bars. There's a big green park in front of Fort San Felipe del Morro and the fort itself with beautiful views. Any of these spots will do depending on your taste. But my favorite is the fountain that sprays from the ground in the Plaza del Quinto Centenario (look for a big phallic monument, can't miss it and kids playing down the steps from there). If you don't mind getting a bit wet and have a good grip, I'd wait until the return trip from the fort back through Old San Juan cause she'll least expect it. Good luck!

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