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Dec 2011

Not to be a Scrooge, but the holiday season is just the absolute worst when you have a significant other. It’s not only the standard dilemma of what to get, but there’s this whole other set of rules that comes into play when you’re dating someone. It’s the “How-Long-Have-We-Been-Together Factor.” What you give her is often a reflection of how long you’ve been together, which means you end up with a six-pack, and a night spent half-heartedly clicking on all those sale notices stores have been dumping in your inbox.

But praise the saints (St. Nick, rather)—Hollywood’s got you covered. Feel free to take note and steal those romantic ideas from the love-stricken characters on the big screen. Yes, there are a lot of chick flicks on this list, but that’s mostly because the Terminator is too busy terminating to get all warm and fuzzy for the holidays.

You hooked up for the first time two nights ago, but you’ve been talking:

First off, this was horrific timing on your part. Why would you do that? Sigh. Just shoot her a text—or, you bold man, you!—an actual phone call, wishing her a happy whatever politically-correct holiday she celebrates, which you should know (and no, a “Happy Holidays!” sent on Christmas Day is not holiday-neutral). Sorry, movies really don’t cover this for you. So we’re just going to start with practical advice to help your clueless soul.

Third date:

This is possibly even worse timing than No. 1. You’re (probably) on your way to a relationship, but you’re still kind of getting to know each other. Thus, the gift must be small, yet meaningful enough to show you were paying attention when she waxed philosophical about the National. Perhaps concert tickets to a band you both like, a la Going the Distance? It doesn’t have to be a big show at a big venue—sometimes the most intimate ones (read: slightly sketchy bars) are the best.

Together two to six months:

This is the time to show her just how much you’re into her (this isn’t really to be viewed as a sliding scale but a statement). If you both live away from family, have a holiday for the both of you; Spend a lazy morning in your pajamas, take a wintry walk outside, do up a nice dinner for yourselves. Gifts at this point can be a spectrum of things: a nice piece of jewelry (please, no diamonds. Try something nice, but meaningful, like the gorgeous-but-unadorned-with-precious-jewels necklace Alan Rickman’s character gets his…erm wanna-be mistress in Love Actually), a little something that comes in pink-striped tissue paper, or tickets to the ballet she wants to see. Yes, the same show you’d rather spend hours shopping with her girlfriends on Black Friday at Nordstrom than attend.

Living together/one to two years:

If you guys still aren’t at the “getting hitched” stage (whether the feeling is mutual or not), it’s a good idea to avoid anything that comes in a velvet box, unless it’s far more of a rectangle than a square. Other things that are nice include a small trip away (no matter the duration, destination or budget, she’ll love the thought), or, per Marley and Me, something that’s small, fluffy and occasionally makes barking noises when it sees a mailman (note: this is only if there’s some commitment in your mental roadmap because if you’re not living together already, guess who she’s gonna call for pet sitting duty?)

Together +3 years

Oh, I don’t know…a ring? Or, you could pull a Noah (a.k.a. Ryan Gosling) and give her a house you built yourself while struggling to wade through an ocean of masculine emotion that abates only with the tides of whiskey and gin with which you’ve filled your heart. On second thought, skip the alcohol bit. Additionally, if you’re not sure what this refers to, you should probably watch The Notebook with her. It’s been long enough, sir.

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