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Proposing Part 2: How to propose to your boyfriend
Posted by Ariel · Advice, OMG OBT

16 Jan 2009

Last week's Why you should propose to your boyfriend post was a big hit, so I'm continuing on with Part 2: HOW to propose to your boyfriend.


Of course there are as many ways to propose to your boyfriend as their are people reading this website, but when considering proposing, here are a few things to consider:

  1. Have lots of conversations with him about marriage and commitment, so that you know you're on the same page. Do you share ideas and values? Do you share a common outlook? Do you both want to do this?
  2. If you're not sure he'd feel comfortable being proposed to, find a casual way to find out. Share a story about another woman who proposed (I've got one coming up for you!) to see how he responds.
  3. If you want to really twist the tradition on its ear, consider asking his mother for his hand in marriage! This list of how to ask a man for his daughter's hand in marriage is actually pretty helpful, and has the bonus of being slightly amusing when you flip the genders: "Promise [her] that you’ll take care of [her son] for the rest of [his] life."
  4. Pick a symbolic gift, if you want one. It totally doesn't have to be a ring (who remembers the "engagement lighter" mentioned in my book?)
  5. Start scheming! The web is FILLED with proposal ideas, but I'm guessing crafting one unique to your relationship would be way more special than any over-engineered feat of romance.

Want a great story to use as an example? Keep hear how one OBT member proposed to her boyfriend…

How I proposed to my fella

by OBT member Helen Waters
So, while I suppose the truly offbeat thing is to propose on any old day of the year, I decided to propose to my fella on Leap Year day of 2008.

We'd long since gone from "if we get married" to "when we get married", but there was no real sign of us making it any more official… So I took things into my own hands.

I bought us flights from the UK to Krakow and put us up in a posh hotel, and asked if they could deliver some champagne to the room.

The champagne duly arrived, and Dom got a bit exasperated: "We haven't ordered this, are you gonna charge us? We're not paying a premium for this overpriced muck!" etc, but eventually I convinced him to drink some (!) and gave him this…

Which he had a good look at, then in the middle there was a small box which contained a small tube of lovehearts (bit corny I know, but there was a good reason behind it going back to the start of our relationship, but that's even more vomit inducing so I won't bore you…) each of which said "marry me" on them.

He pulled one out, looked at it, said "aww," then ate it. Without saying anything else!

…To be honest I wasn't sure what to do then, so I kind of spluttered, "No, I'm really asking you!" (and resisted saying "you moron, I didn't bring you all the way out to Poland to give you a sweetie"). At that point to my relief he said YES YES YES (or words to that effect).

I hadn't bought a ring, but I had come prepared…

With engagement STRING of course!

Anyways, we went on to have a wonderful time in Krakow, which is a beautiful city, I recommend a visit. There were happy faces all round. We were married in August of 2008:

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Comments on "Proposing Part 2: How to propose to your boyfriend"
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1

abandoning eden
January 16th, 2009 · 5:33 AM · #

I proposed to my fiance. We had been talking about marriage for months, and then one day last June while we were camping in the middle of a thunderstorm I decided that if he was willing to come camp with me and walk around in the rain when he hates camping and the outdoors (he has a lot of allergies), because he knows I love camping, then he must really really love me. And once I knew that, I knew I was ready to marry him. He was already sleeping next to me in the tent, so I didn't tell him this at the time.

Two days later I called him on the phone so he could pick me up from work, and while on the phone (like 5 minutes before I was going to see him in real life), in the middle of crossing a street, I was all "Lets get married for reals!" Yes, I actually said "for reals" while proposing. :) And he said yes. About a week after that we set the date and started telling people about it. We're getting married on May 17th 2009.

So that's my super romantic story. I proposed to him over the phone in the middle of crossing the street. :)

2

Sara
January 16th, 2009 · 7:18 AM · #

Aw, both these stories are super-cute! My fiance and I are incredibly lame – we just talked about it all the time and finally just picked a general date for our wedding(Oct. 2010). That's it – no proposal, no rings. It's like a postmodern engagement. Or something. Anyway. Good luck to all the ladies who are considering proposing!

3

Susan
January 16th, 2009 · 9:07 AM · #

That dress! I have mentioned this in some forum on the Tribe but I LOVE that dress!

4

Alison
January 16th, 2009 · 9:15 AM · #

love it!! That is so reaction by hubby would have had to. For sure. haha

5

Molly
January 16th, 2009 · 9:26 AM · #

We live in a deeply sexist (+ homophobic) culture, and it takes real courage to break the mold… Yeah for Brides proposing!

To add a queer perspective, my community sees me as femme and many were confused that I proposed to Laurie…ugh! Whoever you are, forget the passed-down cultural conversations and deep-rooted gender roles. Be yourself. Marriage is a unique expression of yourself…If you know what you want, go after it! Male or female, proposing will take courage – and it’s very fun!

My proposal: I proposed to Laurie on our 3-year anniversary at the soccer tournament where we first met…I gathered up a team (I don't actually play soccer – when we met, I was a spectator :-) , a theme (Chicks Ahoy!), some practices (did I mention that I love her a lot), and 8 months of secret planning with the festival organizers.

During the Opening Ceremonies couples that met at the festival were asked to come forward & tell the hundreds of players and spectators how many years ago they met. We went last…It was a surprise to everyone – even our teammates!

6

Molly
January 16th, 2009 · 9:27 AM · #

I thought I embedded the proposal…here it is:
http://www.youtube.com/watch?v=Ge0YlUSz0RY&eurl=http://mollyandlaurie.nearlyweds.com/storytimes/index

7

Lani
January 16th, 2009 · 10:30 AM · #

I think Helen wins the prize for the CUTEST bride of 2008. She's the most adorable thing I've ever seen. She and her now hubby are sweet. :)

8

Kris
January 16th, 2009 · 12:04 PM · #

My fiance (I LOVE saying this!) and I had just had one of those long conversations (on of many) about our relationship and our future where you look at the clock and say how can it possibly by 1 am, we have been talking for 4 hours about this. And then I got to work and read your first post about proposing to your girlfriend. I was inspired by all the comments, and thinking of making her breakfast in bed this weekend, and asking her to marry me. But by the time I came home, I just couldn't wait, and said so "Are we engaged yet?" She asked if I wanted to be, and then we both asked each other and both said yes. It was such an ordinary moment at home, and yet totally thrilling, and completely us. We went around the corner to our local bar/store and bought champagne. We started announcing our engagement to friends and family later that night. I was blown away by how different it felt once we the congratulations started pouring in from people who have known and loved us these past 3 (almost 4) years. We have been nothing but mushy since. Neither of us thought we could feel any more deeply in love with each other, but somehow we do! So, to other girls out there, just do what feels right and enjoy it…with or without a ring or a big surprise!

9

Tristen
January 16th, 2009 · 10:12 PM · #

Wow, how did you make that box thing? Where can I find that?

Kudos for you both!

10

Brandi
January 16th, 2009 · 10:18 PM · #

I didn't propose to my honey, I will admit.. BUT I did ask him out first for the first date.. so that's got to count for something! :P

BTW, cute article, love the little box thing!

11

Helen
January 17th, 2009 · 12:56 AM · #

Thanks for the nice comments guys! I did make the box from instructions here http://glitteradventure.blogspot.com/2006/11/exploding-box-class.html It was pretty fiddly and took HOURS (especially as I was having to hide the evidence so Dom didn't get suspicious… although I obviously shouldn't have worried about him catching on based on his initial reaction to the proposal…!)

Congrats to all you other ladies who have taken the initiative and proposed to their partners. And special congrats to my friends Emma and Paul who got engaged at New Year when she asked him :) xxx

12

Rachel
January 17th, 2009 · 9:36 PM · #

The more I thought about I realized that I sort of proposed to my fiance. We had been talking about getting married for a long time and we kind of knew we wanted to get married in October of this year.

I had the week around Halloween off from work two years ago and I was cruising around the computer when I decided to see what day Halloween fell on in 2009. When I saw that it was a Saturday, I immediately called Tom and said "Let's get married on Halloween!" He said "HELL YES!!!" Not real romantic. He was at work and I was sitting at home in my pajamas.

February 15th we went out to dinner at one of our favorite restaurants "The Dead Fish" (yeah, that really is the name) and he pulled out a ring and asked me. He felt he needed to do it to make it official even though we had already announced it to everyone. He's so cute in his surprisingly traditional ways.

13

Freya
January 17th, 2009 · 11:07 PM · #

Love the box with all the memories in it.

My proposal was a little more subdued. I had planned on going to the Botanical gardens, which is where our first date was, but I got too impatient and the rings were burning a hole in my pocket! So while we were in bed watching TV I turned and gave him the short spiel of why he's the one for me and presented the vampire teeth rings. It was perfect because we just got to cuddle and be gross without worrying about people afterward :)

14

Louise
January 20th, 2009 · 4:15 AM · #

I proposed to my boyfriend, but it wasn't exactly planned… We'd had lots of discussion about how we would spend the rest of our lives together, but we'd also had lots of conversations about my reservations towards marriage, as a feminist and someone who is bi and has always been heavily involved with queer rights. He always used to say to me, 'I would ask you to marry me if I thought you might say yes', which is almost a proposal I guess.

Anyway we were out clubbing with friends one night, both pretty wasted, and I realised something that I immediately shared with him – 'I know I want to spend the rest of my life with you and you know you do, but what about everyone else? Why don't we get married?' He looked thrilled and said yes, and then I realised I'd done it wrong so I made him sit down so I could get down on one knee and ask again properly. And then we went and found our friends and told them all.

15

Ruth Johnson
January 20th, 2009 · 8:55 AM · #

My boyfriend and I are one of those corny couples who just knew we'd be together forever even before we were "officially" dating. He's been planning his proposal to me for a long time now, but obviously won't tell me one single detail. If I popped the question to him, he'd be pissed! All that planning for nothing! ;) Love the idea, though, and all the stories!

16

princess lasertron
January 20th, 2009 · 11:07 PM · #

I love your story! your photos are beautiful, you look gorgeous, and I love your brightly colored flowers.

I proposed to my husband too and I made him a little book. I made a post about it too here, in case you care: http://www.princesslasertron.com/2008/03/part-million-in-my-wedding-series-of.html

You are so creative and he is lucky to have you!! :)
xo

17

Jenny
January 20th, 2009 · 11:30 PM · #

Thank you for this post! I proposed to my boyfriend this past August. We had been together 6 years, and I had always kinda been against marriage. Then I realized that it was more the wedding than the marriage part that I didn't like, and I was interested in all of the legal benefits that marriage brings. And the CA supreme court had just started allowing gay marriage (that was before the horrible Prop 8), which made me feel more comfortable about the institution as a whole. We are both avid hikers, so I proposed at the top of Mt. Whitney–the highest point in the continental US. I lugged champagne up there to celebrate and had a friend take pictures. No rings. I wouldn't have it any other way!

18

Mary T
January 22nd, 2009 · 3:43 PM · #

I never comment on here, but I will say that in a really embarrassing situation, I did ask my husband first! I have to say it's really true that you just "know" and with him I knew right away. Not long after we met he took me to a huge party with all his friends, who all despised his ex, so I was very nervous about making a good impression. So I drank a lot of sangria to loosen up. Big mistake. (Despite taking up residence in the guest bathroom for the evening, I managed to make a good impression.)

Somewhere in the hours that my then-boyfriend hung out with me, even literally holding back my hair, in the bathroom, I realized that only someone really special would put up with this. So I said, "Will you marry me?" and his response was, "Yes. But not yet."

We got married a year and a half later. ; )

[...] Which leads us to Proposing Part 2: How to propose to your boyfriend. [...]

20

Allison
February 11th, 2009 · 10:42 AM · #

I started reading this site today…. now i ponder… do I propose to him hmmmmmmmmmmmm though i'm like alll me thinks he's surprising me this weekend… but i called him on his oh I have army stuff v-day weekend but he really had it last weekend. He ignored the comment though. WTF. gerrrrrrr he knows i hate surprises.

I always said I'd propose.. but we still have a religion issue to work out :/

21

Kendochick
March 7th, 2009 · 11:11 AM · #

LOL – I totally proposed; we were talking about it one night, and I went off on a rant about how rings were arbitrary and who came up with rings symbolising engagement, anyway? Off the top of my head, I said something about, "Why not an engagement spoon? That would be awesome!" Long story short, a little while later I realized that this was the person I wanted to spend the rest of my life with, went to Birks and bought a sterling silver spoon engraved with the word "Mine" (a long-running in-joke) and our initials. He was thrilled and we're getting married on July 10, 2010!

22

jenmarie
March 9th, 2009 · 12:17 AM · #

i started to propose to the boy last week… by drawing a sharpied ring around his finger while he was sleepysnuggled around me (which is unusual in and of itself… he's usually the little spoon) but i chickened out on the followthrough. i just told him i marked him as mine when he noticed. he was pretty proud to announce the sharpie ring to our friends later. we've only been together a year, and while everything's more incredibly warm and fuzzy than we could imagine, i think he needs a bit more time…it took him a couple months longer to say i love you and then a few more to say it all the time. on the flip side, he's just travelled through amsterdam on the way to france and the space cake reorganized his brain a bit and he's feeling more than a bit sentimental – he's talking about coming back early for me. he'll be back in two weeks… im hoping to make things happen soonish though. thoughts?

23

Kendochick
March 10th, 2009 · 3:43 PM · #

In my estimation, it's not the length of time you've been together that matters when it comes to realizing that this person is IT. If you've got the warm fuzzies and it's mutual, go for it! When it's right, it's completely right … my fiancee and I have known each other for years, but have only been dating for 5 months and engaged for one of those. We both just knew that this was a lifelong kind of thing. Cheers!

24

Carri
March 16th, 2009 · 2:38 PM · #

My fiance and I had been together just over 4 years when we decided to get engaged…although we have lived together the entire time and have an almost-3-year-old son together.

He was married before and apprehensive about getting remarried because of how horrible his ex is, but we finally jumped into the offical engagement deal about a month ago. I guess in a way, I proposed to him, and in a way, he proposed to me. It certainly wasn't superbly romantic or over-the-top, but just coming to the conclusion together that we *really* wanted to get married was one of the most heart-fluttering experiences of my life. We went to a pawn shop together with our 33 month old son and picked out a ring together. It was fun and boring, all at the same time!
We're gonna get married at the end of August or on the first Sunday in September (waiting to confirm a date with our venues). Yay!
I think it's great for a chick to propose to her fella…I thought about doing that a few times with my FH, but it just never seemed right for either of us. We've been making decisions together for 4 years now, so this was just another thing (a big thing, though!) that we decided on together. :)

25

MzFitz
April 14th, 2009 · 7:36 PM · #

Alrighty, I'm going to do it! My BF and I have been talking about it, and we're going to his hometown, where we met, to have his grandmother's ring made into mine/ours/?. We decided that we'd let people know at that point, and have already started planning. I came up through several conversations, so we decided together, but I know we're going to get questions about how it happened, so I'm going to make it "happen."

He's got a show in DC next Friday, and one of the other bands that he's playing with has mutual friends who were playing in another band the night we hooked up. I also wish that I hadn't bought him a new snare drum for birthday and Christmas, as that would make a nice ring, but an engagement skateboard is totally going to have to make up for it! I am so excited!

26

MzFitz
April 14th, 2009 · 7:37 PM · #

By the way, I have always asked my dates to proms, etc. This is WAY more exciting!

27

Kendochick
April 14th, 2009 · 7:59 PM · #

Kudos to you, MsFitz! Congrats!

28

Jazminealthia
June 30th, 2009 · 12:55 PM · #

I'd only had a few dreams about wedding related things. I wanted my dad to give me away, I wanted to wait to move in with my man until after we were married, and I wanted the grand romantic proposal.

Well my dad passed away last August, and because my roommate decided to buy a house (and gave me 45 days notice) I had to move in with my man. So I decided, hell with it. I love him, I know what I want. We have conversations about the future involving us and kids and all that… about how well we fit together.

This past weekend he had a disc golf tournament, his first one. He got 6th place, which he was incredibly stoked about. So I went out and I got a disc that he'd been lusting after. On the underside, where he normally writes his name and phone number, I wrote his name, and my question – "will you marry me?" I took all his discs outside and we were practicing putting. I had gone out to retrieve the disc and handed it to him while he was standing up on the deck… it took him a while to process, once he got over the excitement of the disc and turned it over and read it. But he walked down the stairs, put his head on my forhead, and said yes, of course I'll marry you.

I had been so worried about him not wanting to tell anyone about it – he works construction and he has a bit of a brutish boss. But he didn't care. He thought it was awesome that I did it, that I planned it perfectly. He said, "I don't know if I can find you a ring more perfect than this."

29

Caroline
July 14th, 2009 · 10:17 PM · #

Ruth, I am in the same boat entirely. I've been told I'm not allowed to propose to him because he is way too into planning it. It's true, he's very romantic and loves all the corny over the top stuff (so do i), but I'm getting impatient :)

30

Hiisi
August 2nd, 2009 · 3:26 PM · #

Someone I know proposed in a fancy dress larp! It was very romantic, the genre was pirates of the Caribbean and when we stopped playing, right there, on the beach, we saw a man kneeling down and picking a ring out of his pocket. There were plenty of hats thrown in the air and "Yarrrr"s! :D

31

Andrea
August 18th, 2009 · 9:46 PM · #

I just proposed to my boyfriend of 3.5 years (now fiance), and it was very successful.

Frank's dad (who is also named Frank) has the single largest collection of antique snap cufflinks in the US. They're really quite pretty, and one day my Frank will inherit them (which he's very excited about).

I don't really give a hoot about most wedding traditions, and I've been ready to get this show on the road for about a year now. I decided that, rather than continue to wait for him to make the grand gesture, I would take matters into my own hands and do the asking. He doesn't own any rings, so I had no idea what his ring size would be or how I could find that out without tipping him off, so I decided to propose with cufflinks.

I scoured the internet and eventually found a beautiful pair of snap cufflinks for sale from an antique shop in the middle of Pennsylvania. As a happy coincidence, we had a vacation to Iceland planned. As I was planning out the trip, I selected a location: the Godafoss waterfall. The waterfall was so named because a tribal leader, in seeking to unify the country, made the decision to throw the effigies of the tribe's pagan gods over the waterfall. I liked the story, and the pictures of the waterfall I found online were pretty, so I figured that would be a good spot. And it was.

We were hungover and sleep deprived, thanks to my brother and his girlfriend and their hard-partying influences, but it didn't ruin the moment one smidge. Frank was at the edge of a cliff, taking pictures of the waterfall, and he turned to hop on some rocks and try to get closer when I called for him to stop and said I wanted to ask him something. He came back, mildly annoyed, and I whipped out the box with the cufflinks and asked him if he'd marry me. He was speechless for a few seconds as he looked at the box, and then he said, "Of course I'll marry you!"

And then we made out.

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