The holidays are amazing. (There, I said. At this point, you’re probably thinking, “And water is wet, idiot.” ) Your girlfriend is amazing. Ergo, 2 plus 2 makes 4 and you should combine the holidays and your girlfriend to make an amazing proposal. Right?

Well, Uncle Jon here to rain on your parade. I’m not trying to dissuade you, but….No, actually, I am. Don’t do this.
Ok, well, don’t do it until you’ve thought through these points. Running the holiday gauntlet between Thanksgiving and New Year’s is tough enough without a proposal. Still, a holiday proposal CAN be a great idea. However, like anything in life, it can backfire if you don’t think it through. Cool your jets, lover boy. Read the damn blog and THEN you can decide if this is right for you and your little lady.


1. It’s adorable.

It’s like a Lifetime movie and a Hallmark card had a baby. That baby is your life. Seriously, a proposal on Christmas Eve….Soft, warm holiday lights in the background…Chilly and clean winter air… Lazily falling snowflakes…The love of your life overcome with Christmas spirit when you propose….It’s too cute.

2. The family’s already in town.

Maybe you’re a smart guy and you planned this Thanksgiving freaking miracle of a proposal so that you can go to her parents’ house next week and show off the rock you got her. Regardless, you’re using your time efficiently. You have a ready-made post-proposal party. (Maybe you’re just trying to get the most out of your time at the family’s place for Turkey Day. Hey, no shame, man.)

3. Thanksgiving or Christmas will always mean something more.

Does the idea of you and your beloved curling up together in front of a crackling fireplace with hot toddies in hand post-proposal make your heart melt? Congratulations. You will always associate that warm holiday feeling with your loved one.

Doesn’t this sound great? Take another hit, Cheech. This is a pipe dream. In reality, this idea is a ticking time bomb. Here’s why.


1. You’re turning your fiancee into that poor kid who was born on Christmas.

Instead of giving her something to celebrate in, say, the middle of January or March, you’re associating the holiday season with your proposal. She might be excited by this. However, there’s a chance that she will feel a little disappointed. Will Yuletide feelings of peace one earth mingle with her fond memories of you asking her to be your forever? Or will she think you copped out?

2. It’s so cliche.

This doesn’t mean that it’s not cute. Just realize that “cute” and “smarmy” are interchangeable. This depends on your fiancee. Will she think finding the ring in her stocking makes this the best Christmas ever? Or will she roll her eyes? Remember, it’s more about how the two of you feel. I personally think it’s a snoozefest, However, if she thinks finding a Ring Cam under the tree is the sweetest thing, then proceed.

3. Do you want her family to be upfront and personal in the proposal?

If you propose before Christmas, realize that she will be showing her family this ring with a glass of eggnog in hand. Are you ready to chat with Uncle Bob about your future plans while you both are wearing ugly Christmas sweaters? If dodging questions from her sister about the price tag doesn’t sound fun, then maybe wait until after the holidays.

4. She’s incredibly stressed out.

Maybe you’re Buddy the Elf this time of year, but she’s ready to burst from holiday stress. As an unmarried man, you’re spared some of the most odious aspects of the holiday season. You can do all of your Christmas shopping in 2 hours. While half-drunk. On the 24th. Your mom doesn’t recruit you to help make a small bakery’s worth of twelve different types of cookies, pastries, and tarts. You don’t have to festoon the house with a Hobby Lobby’s worth of tinsel and flowers.

Your girlfriend, however, probably spends hours hunting for the perfect Christmas gift for that one aunt she only sees once a year, baking cookies no one wants, and making your living room look like Santa’s workshop. You associate the holidays with holiday joy; she’s ready to slap Great-Aunt Meredith for making comments about how her macaroons are subpar. Seriously, she’s a pressure cooker. If this is the case, it’s best to wait until after New Year’s.

My snarky wisecracks aside, proposing during the holidays can be an amazing way to make your babe of a girlfriend your babe of a fiancee. If you’re hellbent on playing “Jingle Bells” and having a candy cane in your mouth when you propose, then ignore my eye rolls. I know I’m a curmudgeon.