Seeking Creative Ways to Propose

Updated on December 14, 2009
V.H. asks from Elmwood, IL
11 answers

Hi Moms! I need your ideas and suggestions for a friend of mine. Almost 2 years ago I set one of my closest childhood friends up with a guy that my husband and I are friends with. They hit it off and almost two years later, he is ready to propose. My friend has never been married and is almost 38 years old--she was holding out for Mr. Right and definitely found him! Our guy friend that we set her up with is divorced and has 3 children from his prior marriage. They have such a wonderful relationship, she loves the kids, they love her and I couldn't be happier for them. So last night our friend called and said he bought a ring and is going to propose--but with this being his 2nd marriage and her first he has NO idea how to do it. He knows that he does not want to propose on Christmas. Do any of you have any creative, fun, romantic, etc. ideas for a proposal that I could share with him? He does not want anything "cheesy", but is just looking for some ideas to help him out. Share away, gals!! Thank you :-)

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N.P.

answers from Chicago on

since he has 3 kids it might be cute to put them in shirts - one saying Will the next saying you the next saying marry and then him wearing one that says me?

Not very romantic but might work.

Theknot.com has proposal ideas from what I understand.

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H.L.

answers from Chicago on

First of all, Happy Anniversary!!

My brother wrote a short story about their courtship, took pictures and also drew them to illustrate the book and made a book on http://www.mixbook.com. It was really cool and she has a memento to keep!! He could have his kids help with drawings, story and picture ideas too!! At the end I think he said something like and "if she accepts..." (next page) "THEY LIVED HAPPILY EVER AFTER!!" She looked up from reading and he was on his knee. Just a suggestion.

My husband took me on a memory walk of our first date.

They have a really cute Precious Moments figurine that has a boy on his knee with a ring and a note that says "Will You?" and boxes for yes and no. So cute and he could just put the ring over part of the figurine and give it to her as a gift (not necessarily for Christmas.)

SO there you have it. My ideas. Hope they live Happily Ever After!! Also happy anniversary to you again!

H.

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E.B.

answers from Chicago on

My husband proposed to me at Millennium park in downtown Chicago. I had NO idea it was coming. I would suggest he take her either some place special to them or some place that they can go back to just do the basic proposal. Having a special place to go back to will make it memorable.

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G.T.

answers from Chicago on

One of my favorite proposals had a similar set up. They were both young window/ers, he had a little boy. He asked her to dinner. Called that evening and said he'd be a little late, so to meet at the restaurant. Waiter had her all set up with champagne because he was sorry for his tardiness. In walks the young son and the boyfriend in tuxedos. The little boy got down on his knee and asked her to be his mom. Then he followed with his could-have-been typical-down-on-the-knee-proposal. Maybe this could be altered a tad to suit your friend.

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A.A.

answers from Chicago on

My husband proposed at a park that was a special spot for us. Just the two of us, he had packed a nice picnic, bottle of wine, my favorite flowers and things to eat. He did it on sweetest day, so I was surprised when he took out the ring. I thought I was just getting a romantic sweetest day picnic. It was intimate and romantic, exactly what I would have wanted. I had made it clear that I didn't want some public proposal in front of my whole family or written on the Jumbo-tron at the Sox game. I think taking her to any place that has special meaning for them as a couple and getting down on one knee can't be beat, even if it isn't exactly original. The other thing that may be good for him is to involve the kids in some way, because she really is saying yes to the whole package.

The only really creative thing I've heard of personally is a friend of mine sent his girlfriend on a scavenger hunt around town to all their favorite places. When she would get to the next place she would get a clue to the next place. (favorite restaurant, coffee shop, book shop...etc) The last clue lead her to a place they had their first date and he was waiting there dressed in full tuxedo with the ring. He has always been creative like this and he did it around her birthday so she wouldn't be suspicious of a proposal at the end. It took a ton of leg work though, organizing the hunt and getting the owners to participate giving her the clues. Very unique and sweet though! Good luck and congrats to your friend =)

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T.K.

answers from Chicago on

If he wants to be able to revisit the spot for years to come, he should do something in nature. Buildings, restaurants and businesses come and go. The lakefront, Buckingham Fountain, a forest preserve, etc. is likely to always be there. Choose a spot that is meaningful to both of them. As for the details, only he can answer that because it should be something special to the two of them.

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J.H.

answers from Chicago on

How is his penminship(sp?). When my husband proposed he wrote out a letter to me telling me how wonderful his life was with me now in it, and at the end asked me to be his wife. Now I still have that letter and will always be able to loook at it and remeber that moment with him.

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S.B.

answers from Chicago on

Hello,
Maybe go downtown to look at the Christmas decorations. He could propose by the big xmas tree in the plaza, or a carriage ride, or even over by Macy's!!!!

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J.M.

answers from New York on

Well I dont have tons of ideas but I do have two cute ideas for your friend. First one is he could wrap the ring up in a series of boxes wrapped up for christmas. The ring would be in the smallest box. The second idea is he could propose on top of the empire state building. Its a bit cliche but its a classic way to propose.

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S.P.

answers from Chicago on

If he is afraid of her turning him down because she might be apprehensive about how his kids would take it. Maybe he could have the kids take part in it, like holding up signs with the proposal and he could hold the ring. This way she would know the kids accept her too.

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A.W.

answers from Springfield on

I don't know if they're Christian or not...but my husband proposed to me by washing my feet. He was waiting in my house -- basin and towel ready -- until I got home from work. When I walked in, he sat me down, took off my shoes and socks, and washed my feet. He said it'd be an honor and privilege to serve me the rest of his life.

Another idea is similar to the previous poster. A friend of mine (no prior marriage) was dating a guy who had been married before and had a 7-yr-old son. To propose, he had his son go up to her in their home (at the computer...so nothing really special) and he got down on one knee and said "Will you marry my Daddy?" Then Tim came in from the next room holding the ring.

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