How do I talk to my boyfriend about getting engaged?

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Hi Meredith,

My boyfriend and I are in our late 20s and live together. We both talk about our future often. We really love each other and I know we consider the other “the one.” I also know my boyfriend is a planner. He once told me that he knows the day he's going to propose to me. I always assumed that it would be around next summer, maybe even earlier. But recently a friend of mine asked my boyfriend at a wedding when he planned on proposing. When I asked the friend if it was about a year away, she said it was more like two years.

Obviously I need to ask my boyfriend about this and not my friend. It is such a big decision and I do feel like I should have some say in when it happens. I don't want to wait three-ish years to be married, to be honest. Wedding planning takes a long time! I really want us to start our future together sooner than that. That being said, I don't know how to ask him. I feel like it has to be the right moment, but maybe it doesn't? Would love any and all thoughts on this.

– Empty Ring Finger

"I feel like it has to be the right moment, but maybe it doesn't?"

If you want to spend your life partnered with someone, you better be capable of stating your needs, listening, being a little flexible, and doing a bunch of right things at the wrong moment.

Proposals and weddings are very romantic, as is the whole concept of "the one." But the reality is that you're two people in your late 20s who are trying to make plans based on traditions that might not fit your life together. Why would only one of you decide the timeline? Isn’t it more romantic to consider these things together? It's not just some photo op; it's your path.

Initiate the conversation whenever you're both emotionally present and well-rested. Discuss your wishes and plans. Make sure there are small snacks somewhere close (being cranky and hungry does not help).

For this conversation, trade romance for honesty, and you'll get more happiness.

– Meredith

Readers? When would you bring this up?