Proposing Part 2: How to propose to your boyfriend

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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 there 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:

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

  1. 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. 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!

    • This is basically how it went for us. We talked about it a lot, decided that yes, we are both committed to getting married. We decided on a general timetable (a while from now – we’re both still in school), worked things out in our mind, and announced it to the world. I don’t think there needs to be a huge scene in the decision to get married. I’m more concerned that we love each other and are committed to spending the rest of our lives together, which is, of course, what really matters. Besides, it does take the gender inequality out of it – mutual decisions for the win!

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

  4. 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!

  5. 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. 🙂

  6. 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!

  7. 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! 😛

    BTW, cute article, love the little box thing!

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