Gift giving is one of the most dangerous hurdles in any relationship. It is only at the times where we are expected to present someone with a gift that we unavoidably show our relationship hand i.e. how well do you know them, how much do you like them, and where is this relationship heading anyways?

Gifts are the original reason men learned what the inside of the doghouse looked like. (A vacuum cleaner? Seriously?) Judging gifts ranks above even dissecting a voicemail/email/text over drinks with your girls in the world of social sport. As the holidays approach, and the perilous period of gift exchange grows near, I thought I would offer the best gift I have: a cheat sheet for guys (girls have generally got the gifting thing down…sorry guys) of four gift giving scenarios, and how to navigate them without tears on either side. Happy shopping!

The Long-time Love

Congrats on keeping your gift game tight up to this point in the relationship. She is still with you, which means you can relax and get her something practical. Ha! I had you there for a second, right?

Every long term couple reaches a point where they no longer feel the urgent need to impress each other with extravagant gestures, and soon you are having a conversation along the lines of: “Maybe we should just pool the money we were going to spend on each other, and buy that new couch we’ve both been drooling over.” Heed my warning: this is a trap (unless you have kids, and want to spend the money on them, if so, carry on).

No matter what you read in her expression, she doesn’t want you to say: “Sounds great to me, why don’t we go get it right now? Who cares about Christmas morning, right?” And, while she will be ok with that (after all, it was her idea), and will probably be a good sport, what she really wants to hear from you is that you’ve already got something really special planned, so the two of you should save up after the holidays for furniture. Just because you’ve seen each other through food poisoning, family drama, and moving apartments, doesn’t mean romance has to be dead.

So what now? Well, theoretically you know her better than anyone, so if you have an idea of something she has been lusting after but not splurging on, this is the time to go get it. If you are drawing a blank however, you only need to use your resources — in this case, her friends — to get to the bottom of the problem. Call her closest pals, or just the one with the best taste (whose outfit she is always talking about loving after they get together…that one, that’s the friend to call), and throw yourself on their mercy. They will know where she has been shopping, what she needs and wants, and will be thrilled to help surprise her.

If for some reason you can’t go to the shopping squad (for instance they can’t keep a secret), there are a few standbys that don’t get old for a reason. Find a local jewelry designer (Made You Look in Toronto has a whole collective of them), and have something designed just for her. Not a sparkly girl? Think of what she really loves (rare books, concert tickets, a weekend getaway), and do that.

The Secret Crush

You’ve been friends forever or maybe you’ve just met, but one thing is for sure – you want to declare yourself without having to actually…declaring yourself, right? It’s super-sweet romancing time my friends, so buckle up.

If you are fairly sure that she likes you back, and she is currently unattached (an important thing to confirm, so you don’t have any angry boyfriend wondering why you got his girl a gift), you can show her you like her fairly openly. Crushes are the ideal romantic gift-giving phase of a relationship, as the gifts don’t have to be expensive. Now is the time to make her a funny card, an adorable mix tape (ahem, sorry new gen-sters — a playlist), and bring her a cocoa at work. If you do this, and she likes you back, the two of you should have cartoon hearts in your eyes come the strike of midnight on New Year’s Eve.

If you aren’t so sure how she feels, a bit more caution is advisable. This is where humour becomes your best friend. Think of the inside jokes the two of you share (I know you have them – crushes are made of inside jokes), and the things you have in common, and find her a gift that plays back to one of them. You joke about her getting arrested for her habitual jay-walking? Pick up the gold hand cuffs necklace by Jules Smith. You know she is obsessed with Frank Ocean? Get tickets for the next time he will be in town. Show her you think about her, about what she likes, and hopefully she will clue in that you’ve been thinking about more than just being her friend.

The Door-Is-Still-Open Ex

So you still talk and maybe you have managed to remain friends. You aren’t sure whether you are completely over her, and you’ve got no clue how she feels. In this case, you don’t want your gift to send the “let’s get back together” message, but you also clearly don’t want to insult her or give her something that shouts: “FRIEND-ZONE.”

When giving a gift thoughtfulness should be the goal, but for exes, it’s best to modulate this a bit. A random book from the best-sellers rack will state clearly that you’ve put nearly no thought into the pick, but it is equally important that you don’t appear to have put too much thought in. If a gift will take you hours to think about or make, it should be ditched as an option. This means no mixtapes, hand made art, etc. If it has a meaning that is closely connected to a special date or romantic moment you once shared, it is also a no go. So too is anything crazy expensive — nothing says “I want to get back together” like an Hermes box.

Pick a reasonable price point, lets say between $30 and $80 depending on your disposable income, and think about something she would like, but that you wouldn’t have felt was quite enough when you were actually together. A cashmere scarf in her favourite colour? Good. A gift certificate to her favourite spa? Good. A framed photo of the two of you together? Bad. See where I am going here? If you can make it clear you thought about her taste, and also that you didn’t dwell on what you used to be to each other, you will have effectively left the door open for whatever you decide you would like it to be in the future.

The Soon-To-Be-Dumped Someone in Your Life

The tragedy of a relationship souring through the holidays is that it is cruel to do anything about it, and also cruel to fake your feelings. If you get your girl a sweet, romantic, sentimental gift, and then dump her a week after New Year’s, she may have some uncomfortable questions for you. However, I also think it is brutal to get someone a present that tells them you hate them. It’s a fine line, but there are subtle, sophisticated ways to get your point across, and maybe even cushion the blow.

First, commit to spending the amount of money you would if the relationship was going fine. You didn’t have the foresight to end it in November, so this is your tax. If it makes you feel any better, remind yourself this is the last gift you will ever have to get her. Secondly, cross off any classic romance gifts – if she sees a ring shaped box during the holidays, she is going to get the very, very wrong idea.

Now the key to a good break up gift is that it should signal to her that you don’t know her taste at all, while still being nice enough that she should feel like the bad guy if she complains about it. If she has an edgy sense of style, go to Holts and buy her a cashmere sweater set that reminds you of girls name Kitty accessorized in pearls. No, she would never wear it, and it suggests that you are paying nearly no attention to how she presents herself, but it is from a nice store and is good quality, meaning she won’t be able to be completely pissed without seeming like a brat. Meanwhile, she can return it, and get what she actually wants. And while she runs that errand, she will be thinking about how her boyfriend doesn’t really get her, and where could this relationship really go if he wants to date someone who would wear a sweater set?

The other option is to focus on a very random offhand remark she makes, and pretend that you thought she meant that it was her new passion. For instance, she mentions that a character on a TV show she likes is really into hiking. Voila! Hiking boots for Christmas to a girl who has never and will never embrace the outdoors. This has the same “who does he think I am?” effect as the other method, and gives you the opportunity to look like you were really listening to her and trying, however misguided the results.

A final word of advice? If you must break up before New Year’s Eve, be sure to give her enough lead-time so she can make non-couple plans. If that isn’t an option, be sure to do it long before Valentine’s – these tricks only work once before you start to seem like an un-thoughtful jerk.