Perhaps the most interesting question about proposing is when to actually propose. Obviously the answer is “When she will say ‘yes’”. But when exactly is that. Propose too early in a relationship and you are too pushy, too late and you are afraid to commit. Indeed, after a long period of time, one must ask “what is the point”. It is kind of like making a promise after the fact. I’m not saying that people should enter this whole thing blindly, but when the time is right, propose.

So let’s start by looking at some possible moments that may be good for proposals.

• During an argument. Wait for an argument to start (over something trivial, ideally don’t start one on purpose, just let it come) and just pop the words “marry me” into the argument. Not only will this tactic likely catch the proposee off guard, but it also demonstrates that you know exactly what you are getting yourself into.
• On a holiday. Holidays involve concentrated togetherness living. If you can survive two weeks without leaving each other’s site and aren’t ready to kill each other, this is a good thing. So why not make it all worthwhile for your significant other at the end of the journey with a smart engagement ring. If you holiday overseas you may be able to save some money on duty/GST etc. I don’t know much about this, but Will does.
• During some sort of event that you are obsessed with. For instance, if you are obsessed with Tennis, propose during the Australian Open (turn off the TV when you do, otherwise you may ruin your chances). By showing that she means more to you than your obsession does should score you big points.

Big effort helps. The smaller the ring, the bigger the effort needs to be.

So when in your relationship should such an important decision be made? Before living together? After living together? Both can work. Both have worked. But waiting too long seems to be a waste of time for both people. Why? The answer is simple: Anniversaries. I’m not talking about the anniversaries of living together, I’m talking about bona fide wedding anniversaries. Quite frankly you aren’t in a good position to reach your Golden Anniversary (50 years) if you don’t get married till 50. Besides, who wants to spend most of their married life too old to enjoy it?