Ask Jason: How To Propose Like A Pro

This month, our in-house wedding planning expert, Jason Mitchell, gives us a few pointers on getting engaged. If you are planning on getting engaged, send Jason and Men’s Vows any questions you want answered to make sure you’re ready to pop the question.

The time between Christmas and Valentine’s Day is one of my favorites.  It is non-stop celebrating starting with Christmas onto New Years, Awards Season, Super Bowl and ending with Valentine’s! And as a wedding planner this time brings even more reasons to pop the bubbly: it is the most popular time of year to get engaged.

If this is something you might be considering, please see my pointers below on how you can ask like an ace.


DIAMONDS AREN’T ALWAYS A GAY GROOM’S BEST FRIEND

Asking someone for a hand in marriage is the main event, not what accompanies the gesture.  Don’t get me wrong, I love a shiny object in a tiny box just as much as any good gay.  But you and your soon-to-be fiancé might not have been dreaming of your diamond cut since childhood.  That’s okay.  What’s most important are the reasons that have led you to want to marry each other.  Yes, it’s important to mark the occasion.  But that can always be done with an invitation to shop together afterwards.  Not only is this symbolic of building a foundation together, but it’s a fool-proof way for both of you to get what you want.

FORTUNE FAVORS THE BOLD

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Our lives aren’t necessarily fairytales on the steps of the palace, so why would our proposals be?  Have fun if you’re going for the surprise.  Be creative about where you want to ask and who might be around.  If you are people who like to laugh together, skip the romantic restaurant and go for the more memorable moment at an unexpected place or with a flash mob of friends.  Celebrate your new status the following night at your favorite table for two.

BIGGER ISN’T ALWAYS BETTER

Photo: IG @evkev

Photo: IG @evkev

If you know your future husband is someone who would loathe any of the aforementioned ideas, keep it simple.  Shock and tears of happiness are one thing.  Embarrassment is another. You want this to be a night you both cherish forever.

WHAT MIRROR? WHERE?

Think about the camera. Whether you are painting the question in the sky or staying at home perfecting Ina Garten’s Engagement Roast Chicken, chances are this will be a night you’ll want to document.    Whatever the set-up us, be sure to consider what you’ll both be wearing.  You’ll both feel better taking an engagement selfie looking your best.

TELL THE WORLD THAT WE FINALLY GOT IT ALL RIGHT

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Many couples will tell you being engaged was one of their favorite statuses.  Savor it.  Assuming you’re not tying the knot in reaction to a surprise pregnancy, there is no rush to end the chapter in between dating and marriage.  Talk about how you want to share the news, and there’s nothing wrong with doing this slowly.  In this age of social media, the moment it’s posted the word will spread faster than a new Beyoncé single. Be ready to be proud you put a ring on it!

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