Top Ten Holiday Dating Dos

Submitted by SharpMan Editorial Team on Thursday 14th October 2010
In this article
  • Making the most of women’s romantic holiday moods.
  • Make your current SharpWoman think you’re her holiday gift.
  • One Freebie and one important holiday Don’t.

It’s the holidays — time for R.O.M.A.N.C.E.

O.K., so maybe SharpMen aren’t thinking romance, but you can bet that SharpWomen are. That’s right, ‘tis the season to be jolly — and to cash in on many women’s end-of-the-year romance inclinations.

What’s that? You don’t know about the power of the end-of-the-year romance doldrums? Well hear this: just as women are primed for finding romance at weddings, the holiday season makes us all — but especially women — more susceptible to your SharpMan charms. So don’t blow what could otherwise be a phenomenal SharpDating opportunity — whether she’s already yours or on your "To Do" list. Check out the holiday SharpDating scoop:

Do One: Do dress up. Got an office party to go to? Make it an occasion for a Great Date. There may be a woman out there who doesn’t want to buy a beautiful party dress and go someplace fancy, but we have yet to meet her. Call up your SharpWoman, or SharpWoman of choice, and ask her to be your date — like it’s a real date, not an obligation. Hey, why not get a few points on the boss’s bar tab? Alternatively, offer your services as a charming, well-dressed escort to her office party. Every SharpWoman wants one. If neither of you has a formal or semi-formal office party in your future, pick a fabulous, romantic restaurant and take her there — pretend it’s 1940 when people used to really dress up. She’ll love it.

Messed up at last year’s office party? Don’t miss SharpWork’s Office Party Etiquette.

Do Two: Plan a "Holiday" Great Date. The year-round pressure for guys to come up with fun, creative dates can be a drag. Luckily, when the holidays come around every year, this burden is relieved for those guys who cash in on the built-in festive theme of the season. Try planning a Great Date that capitalizes on the holidays. Can’t think of any? Check out SharpMan’s "Special Seasonal Dates" chapter in 50 Great Dates for Any Budget, the busy SharpMan’s bible for quick, inexpensive Great Dates.

Do Three: Do things you wouldn’t normally do. In addition to planning "Holiday" Great Dates, make an effort to feed her holiday spirit in order to transfer that holiday goodwill to you. That’s right, if she’s into the holidays and you add to the merriment, you look good. On this one, little things really do make the difference. Think of small ways to make her laugh and see you as the kind of guy worth spending the holidays with.

Do Four: Do send a gift to her office. You can’t lose with this one — as long as it’s tasteful but appropriately showy. Her favorite cookies? Great. A stuffed animal with a card? Swell. Holiday flowers? What could be better? The gift is nice, but having all of her coworkers know that she’s got someone thinking of her — priceless.

Do Five: Do let her know what holiday events you plan to spend with her. This seems like a no-brainer; basically, it’s just calendar control. Despite this, SharpWomen everywhere can easily recount the New Year’s Eves spent with sniffling girlfriends who thought they were going to have a New Year’s Eve date, only to find their boyfriends spend every New Year’s Eve back home or on an annual road trip with their buddies. Family get-togethers, office parties, New Year’s Eve...these are important to her. Schedule early and be a Great Date.

Do Six: Do listen for other gift ideas. In general, women give better gifts to guys than guys give to their SharpWomen. It’s like some freaky law of nature. While it’s great to be on the receiving end of this equation, you can bet that the second year in a row will peeve-off the giver. So, if she’s already your SharpWoman and you’re panicking about messing up for a second time, simply follow her lead. No need to go to extremes. We’re not advocating a trip down to the dealership just because you know she loves the new two-seater Mercedes (although that would work in a big way). Romance shouldn’t be about tons of cash. On the other hand, your SharpWoman is looking for some sign that you’ve put in some effort to think of something just for her. Make a point of listening to the things she says, the whimsical things that catch her eye when you’re together. In case you still don’t get it, the gift here is the listening part.

Do Seven: Do offer to go to holiday shopping with her. Sure, it’s deathly boring, but this simple act will forever place you in her SharpMan Hall of Fame. Two extra perks? You’ll have someone helping you with your own shopping and you’ll have a chance to implement Do Five.

Do Eight: Do help decorate the tree (or help prepare a holiday meal or bake cookies or bread, if trees aren’t part of your celebration). Tree decorating and cookie making just scream "SharpMan." That’s why she’ll love it so much. But don’t fall asleep or turn on the game (unless you’re both into it) while decorating or baking. That would be hazardous to your health in oh, so many ways.

Do Nine: Do figure out where you stand with her. Not sure where you and your SharpWoman are headed? Consider toning down the Mr. Wonderful act and the suggestions listed above. Believe it or not, she’s evaluating her head off right now — holidays often do that to women. If you’re ready to "move to the next level," the holiday season is the time. This will make all the other Dos a piece of cake, for both of you. On the other hand, if you go full steam ahead with Dos One through Eight, she’ll think you’re madly in love with her — and when you dump her after the first of the year, your name will be mud for many holiday seasons to come.

Do Ten: Do get a portrait made of the two of you. No doubt you are rolling your eyes as you read, but the ladies love this. If you are ready to take the plunge, you will have one very happy lady on your hands when you suggest a portrait of the two of you together — even if she rolls her eyes when you first suggest it. We’re not talking about going and getting one of those goofy "old west" photos taken, where you get to wear a gun, a sheriff’s badge and look sullen (too bad, huh?). We mean a real portrait at a real portrait studio, where you’ll both look great and she’ll look ten pounds thinner.

One Freebie Do: Do give her an engagement ring. OK, so you are serious about her, but you were thinking of waiting until after New Year’s — like maybe Valentine’s Day or her birthday, or the summer solstice or…. Take note, big guy: if you’re at that place and she knows it, you can bet that she’s hoping, dying and praying for that ring. She’s sweating it big time. So much so that no matter what you do this holiday season, she’ll be too busy wiping the sweat from her brow to notice. Sure, it’s tough to be in your position, but consider yourself lucky; most guys have to create (read: pay for) special occasions for the ring ceremony. The holidays are already "special," so they give you a romance freebie. Bite the bullet and go for it. It’ll be your ultimate holiday Do.

One Don’t: Don’t give her jewelry if she’s looking for a ring. While it’s probably bad form to end the Holiday Dos list with a Don’t, we’re in the holiday spirit and want to save you a great deal of anguish. If your SharpWoman could possibly be thinking that you just might be coming through with an engagement ring — don’t, Don’t, DON’T give her any other jewelry in what could be considered a ring box. Really. This one’s for your own good. Just imagine the horror of having her burst out into tears (and not the good kind) when you’ve shelled out good money for earrings, a bracelet, necklace or —worse — a non-engagement-ring ring. To place it safe, whatever you give her, make sure it is wrapped in a box the size of a mid-sized continent.

This article last updated on Thursday 14th October 2010
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