Proposing Part 2: How to propose to your boyfriend

Updated Dec 30 2017

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:

  1. Thanks nicole ill let u know how it goes I'm going to go for it on sat. At his fav resturant. (Fingers crossed) 🙂

  2. Thanks ill let u know how it goes I'm going to go for it on sat. At his fav resturant. (Fingers crossed) 🙂

  3. Thanks ill let u know how it goes I'm going to go for it on sat. At his fav resturant. (Fingers crossed)

  4. I did it I made his fav meal had a glass engraved with his name on it then I light candles all around my room put on a grass skrit and tht was all I did it an he said you know I'm going to say yes so I gave him the ring he told me why didn't u tell me now I have to go out and get u a ring I pulled mines out and said tookn care of

  5. This is so helpful, I've just started planning to propose to my boyfriend of so far 5 months, it may seem early, but he's the one. Not a romantic so if I want a romantic proposal I'll have to do it myself 🙂
    I've planned a ring for him, and now I've just got to plan the rest.

  6. I think I made a big mistake by being defensive about the institution of marriage (my parents and almost every couple I know have ended in divorce) and told him I never want to get married, ever since then I have been trying to revise my statement by adding that although it is stupid to legally bind yourself to a partner that is based on emotions, and not financial profit (or shouldn't be in my book, I am a poor teacher and I don't want to be a burden on him), doesn't mean that I don't want to dedicate my love and non-material qualities to someone special for the rest of my life. I don't know, but although in my mind I have the idea that him proposing would be romantic, I still want things on my terms. I guess I want to propose because if he doesnt agree to be my partner in love and health then I won't need to waste anymore time of his or mine. Can you tell I have dealt with some lazy guys before??? Lol !

  7. I'm considering proposing to my partner of just over a year theres a big age gap of 21 years and I'm only 23, however we are so made for each other, we've talked about marriage before but never getting hinched ourselves , I've brought yellow rose petals my favourite flower , I plan to put these up the stairs leading in to the bathroom and in the bath, with candles lit on the bath edge with a silver trinket box that says will you marry

  8. Hahaha I love this! I proposed to my boyfriend in Novemeber 2004 and he said "No, I'm too young(20)". Then after spending Christmas and NYE together and parting ways Jan 1st 2005, two weeks later he called me and said "Here's my credit card number, buy me a plane ticket and let's get married in 2 weeks". We talked to each others parents and got married Feb 05, 2005. We've been together for 10 years next month and married almost 10 years (Anniversary on Feb 2015). We have a 4 y/o and I'm more in love now than I was 10 years ago. I tease him all the time since I was the one that proposed 😉

  9. My boyfriend and I haven't been dating for very long, but I'm thinking about proposing to him on our six-month anniversary. The moment(s) I realized that I trusted him were on our second date when we laid in my car and told each other pretty much all of our history and then again when we took a trip to California for a week together.

    My relationships haven't lasted for more than 4 months, so if he sticks around for half a year or longer, I'm sure he's the one! What I want to do is give him a customized Legend of Zelda-themed ring box with my favorite Celtic knot ring that he loves so much. Choosing rings together will be pretty easy since we both wear the same size!

  10. I would propose to my boyfriend, but we're not even in the "If we get married . . ." stage yet. Here's what's happened so far:
    I broached the topic with my boyfriend around Christmas 2014, being like, “Having to walk by a bridal salon twice a day everyday for the four months I lived in Japan may have done this to me, but I’m kind of starting to get into the idea of marriage. What do you think?” His response: “I still have no idea.”
    A few days later, my mom started asking me when we were going to do it, because we’d been together just over a year. The second time was when she was driving me to the airport two hours away. Boyfriend and I were planning to move to my hometown in August (now just me — he has another year of school left), so I asked her, “If we can’t find a place to live before moving here, could we just stay with you for, like, a week?” Her response: “In theory, yes, but . . . I really wish you would just get married.” She then launched into a 5-minute speech about how married relationships are inherently stronger because the threat of divorce compels couples to use the tools available (to all couples, really) to maintain their relationship.
    So when I got off the plane I called my boyfriend to tell him what had happened and was so frustrated, confused, and completely turned off to the idea of even considering it if it was just going to look like caving to parental pressure, that I (somewhat rashly) told him she had just killed any desire I had for marriage. He was like, “Okay. Understandably so.” And we haven’t touched it since.
    Eight months later, I feel like once again, I’m back at what I’ve been feeling for a year or maybe two: Legal benefits of marriage, yes. Ceremony, no. Big reception, yes. For all I know, Boyfriend’s still not even thinking about it. This is probably at least partially because I've almost become a bunny boiler on the topic.
    That's not to say I won't show him marriage- and kids-related stuff when it's relevant (i.e., "Would you change your name if you got married?" when I find a hilarious article about it). I just act all neutral about it, like I don't give a fuck personally because I have no idea how I feel about marriage either.
    We live 1200 miles apart now and he plans to make his way to where I am if he can't get into grad school after he finishes this last year of undergrad. So I have no question that he's committed. And not getting married is no dealbreaker for me. I want to stay with him for the foreseeable future no matter what.

    So. How do I undo all of that without making it awkward for both of us? I want to open the dialogue again, but he just plain doesn't like talking or thinking about the future more than he has to.

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