Proposing Part 2: How to propose to your boyfriend

By on Jan 16th

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: