A Naughty List of Christmas Dating Tips

Christmas, dating tips, life hacks, relationships, how to date at Christmas, humor, satire, advice, Modern PhilosopherThe Christmas Season is a time of great joy and cheer, but it can also be lonely and depressing if you’re single.

That’s why I encourage you to see Christmas as the perfect opportunity to finally ask out that special someone.

People are in a better frame of mind this time of year, so you might as well capitalize on that and finally get up the courage to tell your crush how you feel.

There’s no reason to be a Dating Grinch or to say Bah Humbug to relationships.

After all, they didn’t hang that mistletoe for decoration, and the office Christmas party isn’t just so you can exchange cheap Secret Santa gifts.

Since this is the Season of Giving, I’m going to give you some dating tips to help make your days merry and bright this Christmas.  Get ready to learn a few things that might land you on the Naughty List…

Be a Wise Man — Always come bearing gifts when you date at Christmas.  Breaking the ice on a first date can be a real challenge, so why not get the night off to a great start by giving her a perfectly wrapped gift?  It shows her that you’re generous, that you want her to be happy, that you now enough about her to buy her a gift, and that you’re capable of wrapping a present in a pinch.

Christmas, dating tips, relationships, love, falling in love, life hacks, humor, advice, Modern PhilosopherDeck the Halls — It’s Christmas so dress the part.  Put on that ugly Christmas sweater  and show her that you’ve not only got a funny side, but that you are also confident enough to go out in public like that.   Wear a Santa hat because she will be tempted to take it all night, and nothing is more adorable than an attractive woman wearing a part of your wardrobe.  Also dress well, like you’re taking Grandma to Midnight Mass.  You want to show her that you have a sense of style, and that she is important enough for you to break out the nice clothes on a first date.

No Silent Nights — Chat her up.  Don’t allow any awkward silences.  Communication is key in any relationship, and if you can’t keep the dialogue flowing on a first date, then you are never going to get a second date.  Even if you’re not the best conversationalist, it’s Christmas.  Talk about Christmas Carols, challenge her to name all of Santa’s reindeer, discuss the plot of any Christmas movie.  If all else fails, ask her to share her favorite childhood Christmas memory…that should keep her going for a while as you brainstorm for new ideas to keep up your end of the conversation.

Christmas, dating tips, how to date at Christmas, love, life hacks, advice, humor, Modern PhilosopherWalking in a Winter Wonderland —  Christmas provides a natural romantic setting, so make the most of it.  Ask her to go for a walk to look at the Christmas lights.  You can learn a lot about her simply by noting which decorations she points out as her favorites.  Christmas is also a very cold time of year, so she will be inclined to walk  close to you for warmth.  Don’t be afraid to put an arm around her because you thought you noticed she was shivering.  Hold her hand so her fingers don’t turn blue.  Stare deeply into her eyes as you stop to offer her your scarf and then hold that stare as you gently adjust the scarf on her until it’s perfect.

Jingle Her Bells — Make her laugh, dude.  Ladies love a man who can bring the funny, so show her that she can count on you to always tickle her funny bone.  There’s nothing better for your confidence than the sound of an attractive woman laughing at your jokes.

Christmas, dating tips, relationships, love, life hacks, humor, advice, Modern PhilosopherRudolph the Red Nosed Reindeer —  Humans might not be born with red noses like Rudolph, but there is a way to acquire one over the course of the evening.  Drink.  Alcohol will calm the nerves, improve your mood, and make your jokes seem funnier.  Don’t overdo it, of course.  The last thing you want is a drunk date because you have no idea what she’s like in that state.

I Saw Mommy Kissing Santa Claus —  For some reason, that not even science can explain, the ladies have a real soft spot for Santa Claus.  Maybe it’s because he was always the one man who never let them down and gave them anything they wanted.  Perhaps it’s the beard and the way he makes being overweight look good.  Whatever it is, use it.  I’ve already told you to wear a Santa Claus hat.  You might want to bring a Santa’s beard that you can slip on at some point.  Wear red and laugh at her jokes with a jolly “Ho, ho, ho!”.  Just don’t blow it, fellas, by asking her to sit in your lap.  That’s amateur hour!

Christmas, how to date at Christmas, dating tips, relationships, life hacks, humor, advice, Modern PhilosopherThere’s No Place Like Home For The Holidays —  Invite her over to your place for something completely innocent like a drink before you go to dinner.  Home field advantage never hurts, and it definitely helps for her to see that you’ve got a nice home and don’t still live in your parents’ basement.  By doing this, you plant the seed of what her life could be like if you end up together, and it makes the potential relationship seem much more real (especially as she fantasizes about how to fix up your place and make it her own).  The House on the Hill has always been a great wing man for me, so trust me on this one.

Don’t Be Frosty! —  The weather outside might be frightful, but your date needs to be warm and comfy cozy.  Turn on the charm full blast.  Make her feel like the most important person in the world, never divert your attention from her, and hang on her every word.  Make sure she knows there’s nothing more interesting in your life at that moment than her.  Keep adding logs to fuel the fire of attention, and she will never have a reason to seek warmth from someone else again.

Dating, Christmas, dating tips, relationships, falling in love at Christmas, life hacks, advice, humor, Modern PhilosopherIt’s A Wonderful Life —  Do you remember the plot of my all-time favorite Christmas flick?  Make your date imagine what her life would be like if you had never come into it.  Your goal is to ensure that she cannot see a future without you.  Teacher says every time a bell rings, a guy who listens to this advice gets a second date.

Trim The Tree —  Seriously, guys, keep in clean down there.  I shouldn’t even have to tell you that.  The last thing you want is for her to unwrap your package and run screaming because of the forest she finds.  You only get one chance to make a first impression!

She Came Upon A Midnight Clear —  Get your mind out of the gutter!  This tip is to always have her home by midnight.  It shows that you respect her schedule, and are also aware of the ancient warning to never feed a first date after midnight!

I know some of you are probably asking why you should take dating advice from someone who’s single, so I will remind you of a recent quote by The Other Melissa, “You always seem to date women who are way out of your league!”.

That’s most likely because I follow my own dating advice.  Good luck and may you all find love this Christmas Season!

Can’t get enough of this great advice?  Then I recommend you follow my blog and check me out on Twitter and Pinterest…


About Austin

Native New Yorker who's fled to the quiet life in Maine. I write movies, root for the Yankees, and shovel lots of snow.
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