How to know when it's the right time to pop the question

I'm at the age where everyone around me seems to be getting engaged. At 29-years-old rarely a weekend goes by without an engagement party to attend or  congratulatory card to sign.

Log on to Instagram I'll inevitably scroll past happy (heavily filtered) couples beaming back at me.

"Today my best friend asked me to marry him…and I SAID YES," reads the caption, while the likes and well wishes pour in.

It's not surprising and I'm into it, in fact. It's something I've spoken about with my girlfriend of five years. We've jokingly referred to each other as "my fiancée" when trying to score free stuff at hotels and that's slowly led to more serious conversations about when and where we might get married.

Picking the right time, however, isn't as easy as it seems. I know we're in love – so how do others know when to take the next step?

Andrew, 27, recently engaged

"We'd done the milestones"

For many, getting engaged is simply the next step in a long line of things you do when you're happily in love.     

"We had shared so many milestones in our time together, birthdays, travelling together, travelling apart, living together and were still as happy as ever so I thought it was time to experience a few more of the big ones," says Andrew, who proposed to his girlfriend last month after eight years of dating.

"I'd say you need to tick off some of those relationship testing events like travelling together before you know you can handle each other for life."


Sarah, 29, currently engaged

"We survived an interstate move"

There is perhaps no greater sign that you're ready to commit to someone forever if you don't kill each other during an interstate move. At least that what my friend Sarah reckons.

"Imagine screaming at each other, while driving a truck from Melbourne (overnight!) then having to put IKEA furniture together the next day," she explains.

"The interstate move was a major hurdle and we survived it, two months after moving to Sydney he asked me to marry him and I couldn't have agreed more."

Jason, 32, married

"I could afford the ring"

I believe it was the famed philosopher J-Lo who told us that "love don't cost a thing." Turns out she was wrong; money matters and it can often be a deciding factor in when to make your move.

"I'd wanted to for a long time and it finally got to the point that I could afford the ring we both wanted (she wanted)," laughs Jason, who dropped to one knee after four years.

"Honestly though, I wasn't in a big rush and she'd always wanted this particular ring, so to me, it felt right that when I could get it, I should do it."

Aaron, 33, formerly engaged

"I'd waited too long"

Sometimes in relationships, there's a window of time when everything is perfectly balanced and while it might not seem romantic, the reality is if you miss your shot, things can change.

"I knew pretty early on that I wanted to marry my ex-girlfriend, but when she started having some trouble with mental health I waited to ask because she said wasn't ready," explains Aaron.

"But because I'd mentioned it, it was always in the air, then when it didn't happen at that time, it caused conflict."

Eventually, Aaron popped the question and got the right answer, but it proved to be the wrong time.

"In the end, I think that it all built up and became too much of a thing between us, I honestly believe if I hadn't waited we'd probably still be together."

Don't just follow your nose

I made a promise to myself that I would refuse to accept any "when the time is right" answers when discussing this subject. Unsurprisingly, everyone I spoke to ignored me and they all uttered that sentiment at one point or another.

But the other constant everyone mentioned was that you need to weather at least one good test before you commit to each other for life. Whether that's travelling, cohabiting or driving a rental truck interstate, once you've seen your relationship survive (and thrive), then you know you're onto a good thing.

Now, to hire a moving van and drive my girlfriend to Perth – I'll let you know how we go.