“When I propose to my girlfriend, should I do it earlier in the evening or late at night?”

“When I propose to my girlfriend, should I do it earlier in the evening or late at night?”

First off…love the site, it’s actually useful, honest, and has plenty of experience where I have none. I found the girl, bought the ring, have a pretty solid plan, and more importantly have the element of surprise (don’t worry, not so much where her answer will be a surprise). However, I am having difficulty identifying this element. The plan has lots of segments, boat ride, dinner, drinks with friends, hotel, and a few things the next day. Is it better to ask her pretty early on in the night, and enjoy everything I’ve planned? or allow the suspense to build up (even though she’ll know something is up) and ask toward the end?

We’re glad you like the site. And we’re glad you found the girl. (That’s a non-trivial step.) Sounds like you’ve done your homework and you’re in good shape.

A general rule of thumb: think of the proposal like foreplay. Even though the woman knows what’s coming, the best part is the anticipation, the build-up, the tension. You’re right-she’ll probably know what’s up. Unless your lifestyle is very, very different from mine, we’re guessing that boat rides aren’t part of your average Friday night. But even if she’s 90% sure what’s going on…that 10% of uncertainty is what keeps things interesting. This by no means is an ironclad rule. Ask yourself a few questions:

Question 1
Are the friends who are joining her very best friends, or are they kinda-sorta-casual friends?

If they’re your friends-or casual friends of hers-keep them out of the equation. However, if they’re her very best friends in the world, then if you can somehow swing it, a lot of women like to share this joyous moment in person with her BFFs. To clarify: we recommend that you first do your alone stuff. But if you could arrange, say, brunch with friends the next day, then you get the best of both worlds. (Also, if your new fiancée has an in-person brunch to look forward to, then maybe she’ll be less likely to call her friends immediately.) For more on this, see our tips on announcing your engagement.

Question 2
Is she the kind of girl who, after you pop the question, will want a few hours of intimacy and quiet before dialing up everyone she knows?

Many women call up their closest 74 friends as soon as you extend the proposal. If you think this is likely, that’s even more incentive to ask her later in the evening, which could give you more alone time (the theory being that she’s less likely to call old college friends at 3am).

Question 3
Are you going to be stressed, so wired, that you won’t be able to enjoy the evening until you get this off your chest?

Think about this. There’s no shame in it. If you’re paranoid about the engagement, sweating, panicked, snapping at waiters, then you undercut the spirit of the evening. Be honest with yourself. If you’ll be a basket case until you’ve shared your secret, then you might just want to get on with it.

Good luck – looking forward to hearing how it goes. Hope this helps.

-The Plunge

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