Holidays Are The Perect Time for Becoming Engaged

So I have the ring and I’m asking her parents for my girlfriend’s hand in marriage over the holidays. Mainly because it’s so awkward having to answer the same questions every year from her family about when we’re getting married and where would we like to get married, etc. The pressure is ridiculous, but we’ve so busy.

We want to get married and now that my girlfriend’s finishing up her dissertation, it seems like a sane time for the long-overdue engagement announcement. How can I make asking her fun?

–Name Withheld

What’s more magical and romantic than a holiday proposal? Give her a present (the ring boxed and wrapped) Thanksgiving eve or Christmas. Then you can announce your engagement to assembled family members the following day.

You want all the siblings and their families to find out at the same time.

Make the announcement, assuming both she and her parents are into this, as a toast before dinner during cocktails.

While trimming the tree Christmas eve, have her discover the ring as an ornament hanging from the tree.
What could be more fun than ice skating at night? Skate out into the center of the rink and get down on your knee right there to propose to her. Hopefully, it will be gently snowing.
Personally, I always thought being proposed to in the shower would be very sexy, but you wouldn’t want the wrapped ring box soaking wet.

Once I saw a baked apple pie on the Internet once with the words Marry Me designed into the top crust.

Be creative, but don’t get too cute — too cute could be a turn off. It would be one thing if he was a pastry chef, another if his mother made the pie.