Wealthsimple is a whole new kind of investing service. This is the latest installment of our “Dear Ms. Etiquette" series, where our columnist untangles the conflicts that happen when people and money get together.

Dear Ms. Etiquette:

I have to go to a colleague’s baby shower. I hardly know her, and I definitely don’t know her baby. Do I have to buy a gift? If so, how much money is the right amount of money to spend on a random unborn baby?

Oh and did I mention that I also have to go to a wedding in ICELAND later this summer? Iceland seems cool and everything but am I expected to log onto Crate & Barrel and buy them a $275 cheese knife set if I already paid to get myself to freaking Reykjavik?

I’m a little stressed out, suddenly, about all these gifting decisions.

Signed,

Help I’m trapped inside a gift registry

Dear Trapped:

This is a legit line of questioning. Why? It’s gift season. Sounds like malarkey but it’s true. Summer features graduations, weddings, Bastille Day — it’s even true that more babies are born in the summer than any other season and so there are more baby showers. (Note: I realize that no one has ever given anyone a gift for Bastille Day, except maybe Napoleon or Louis XVI — being overthrown and executed is a terrible gift, by the way.)

The first principle to keep in mind as the sweaty gifting months draw near is you don’t have to spend enormous sums of money as long as you make a gift either a) completely useful or b) completely thoughtful. Remember, wealthy people give terrible gifts, too. (Hammacher-Schlemmer counts on it.)

Wait. I lied. The real first principle here is to remember the point of giving gifts in the first place. Is it so you don’t feel dumb at the birthday party? Is it because you feel that society is pressuring you into keeping the great gears of the gift-industrial complex grinding on in capitalistic oppression?

No.

The point of a gift is generosity. As my official rabbinical money ethics consultant, the Rabbi Jonathan Blake, says, “You’re supposed to gift because you’re moved to give.” If you are doing it right, you’re taking the opportunity not to avoid shame or accrue resentment but to feel the little frisson of joy you feel when you give. There are studies that prove this makes people feel good.

That’s the goal here: giving because it feels good to make someone happy. But. Ms. Etiquette also acknowledges that we’re all human and don’t want to be embarrassed at baby showers either, and will take that into account.

So not only will I answer the questions you asked, Trapped. But I asked around for some other tricky present-giving conundrums and I’m going to give you the answer to those questions, too. (Consider it a gift!)

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Problem One: Now about that random baby who isn’t even born yet.

To answer your first question right off the bat: yes, if you go to the shower you do have to get a gift. You should probably get a gift even if you don’t go to the shower. Why? Because a new person is entering the world, which is a big deal even though it is numerically quite common.

Also because people are going to watch you walk in and walk right past the gift table without contributing anything.

Now, how much should you spend? There’s some calculus involved when you’re buying a gift. “The dollar amount is determined by the relationship you have,” the etiquette expert (yes, I’m not the only etiquette expert) Diane Gottsman said when I spoke to her about this. “Not to mention the salary you earn, your financial obligations.” So the point is: spend what you feel comfortable with.

$100 is a generous amount to spend for someone you’re relatively close to. But that’s a lot of money depending on how much you make. $50 is also very generous. Or better yet, ask around to see if anyone you know—someone on the same peripheral friendship tier as you are—is attending. Go in on a Diaper Genie together (it shouldn’t be more than $25 each with shipping, depending on your Amazon Prime status.) Diaper Genies are great, and whenever you pool money with other people to get something awesome you get extra credit. For organizing. And for getting something that's more exciting than burp cloths.

But make sure no one else is buying her one by checking the registry. Which I should have mentioned first: check the registry.

Problem Two: Your cousin, who is a nice cousin but not someone you even know that well, is getting married in Cincinnati. But only expensive items are left on the registry.

Ok, the first rule of wedding gift-giving for people you’re not especially close to is: get to the registry before anyone else. That way, by the time you get there the only thing left isn’t the $300 Waterford Crystal crumb scraper-upper. If you get there early and there are still no inexpensive gifts, that’s a party foul by the happy couple. Gottsman told me it’s their obligation to provide options for people with lots of different budgets.

When selecting from the registry, try not to get the bare-bones-est thing on the registry – your gift of a single salad fork will stand out as almost performatively cheap. People might remember that. And if you’re not trying to be actually thoughtful (always the goal) your aim should be to give one of the countless gifts the bride and groom have no idea who gave them.

If the registry provides you with no answers, there’s a simple non-registry answer: the gift of cash. Money is a good option if you know the couple doesn’t have a giant bank account to start their life together. $100 is a number that will never be offensive to anyone (but feel free to give less; $50 is fine if $100 feels like a lot to you). In my opinion it’s kind of tacky to just hand over actual cash — I like to give American Express gift cards. It feels more thoughtful even though it’s the same amount. And send it instead of bringing it the ceremony – things get lost at wedding receptions.

Problem Two and a Half: That Wedding isn’t in Cincinnati, it’s in Reykjavik.

Remember when I said being thoughtful was a good answer to the problem of not being able to drop a bunch of money? This might be a good time to employ that strategy. Get the Icelandic newlyweds something that will help them pull off the wedding – a bottle of great schnapps for the Icelandic rehearsal dinner. Graft a jade plant from the one you have at home and grow it for them in a nice pot so they have something green in their house. Or do something symbolic: a really fun ice tray (you know, because of Iceland), or a poster from the ski resort where they met on the chairlift that fateful afternoon.

If you aren’t good at thoughtful, give them a copy of the book Cabin Porn. It’s cool, it’ll look nice on their coffee table, and it only costs $25. Again: have it delivered. No one wants to take a coffee table book to, or from, Iceland. Except Vikings, I guess.

Two notes to take into consideration if the couple are Millennials. 1) Millennials it appears, love cash. And they also famously love experiences more than things. Concert tickets, museum memberships, bike rentals, etc. — all good choices for people who live their lives in the moment.

Problem Three: You’re invited to your boss’s small birthday party.

This one’s tough because you’re really threading a needle. You don’t want to look like you’re sucking up to your boss, which is creepy (if effective for certain bosses; but even then you don’t want to do it because it’s yucky). At the same time, you don’t want to be the guy who gets the boss a crappy gift.

First a note to those who have not been invited to that intimate birthday celebration with the boss: no need for a gift, just wish her a happy birthday in the halls, or via your preferred time-wasting office messaging software (which is preferable in this case to your preferred social network).

Second: the best thing to do in this situation is to go in on a group gift with other folks you work with. That way you get a lavish gift befitting the boss but you don’t spend a lot or seem like a suck-up.

But be aware. The great (while also being kind of terrible) thing about bosses is that they know exactly how much you make, so you can stay within your means. I suggest going for something relatively bland or inoffensive. A high-end scented candle is good, or a book by Walter Isaacson – the high-end scented candle of literature. But by all means: say something meaningful, and short, in your card.

And one more note: unless he or she is a jerk, your boss won’t notice the people who don’t give birthday gifts or holiday gifts, only the people who do.

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Problem Four: You find yourself the houseguest of a college friend, because you’re in Cincinnati for your cousin’s dumb wedding.

But wait, you may think. Do I need to give a gift just because I’m crashing for a few nights? Well, yes. You’re saving a bunch of money by staying at your pal’s house. Not to mention that, no matter how much your college friend pretends otherwise, houseguests of any sort, even the best, are a pain in the butt.

But what’s the right thing to get? How extravagant does it need to be?

My answer: bring something that is local to the place from whence you come. Bagels from New York. Brisket from Texas. Plastic surgery from Los Angeles.

Another good bet is: see what their house is missing and get them one of those. Maybe you’ll break a wine glass, and you can replace it with four more. Maybe you’ll miss some household item that you yourself have at home — your beloved toilet-seat cozy! A recent houseguest at my parents’ house mailed over a set of lobster tools after she left—they’d had lobster during her stay, and were one set short. One rarely cited advantage to the human condition is the temptation to catalog deficiencies in friends’ homes – use that information as your guide!

(Note: don’t get them a toilet-seat cozy.)

Additionally, Diane Gottsman says that even if you bring a gift, “You still need to pitch in with the day-to-day chores and take them to dinner, depending on how long you stay.” Why? You’re a member of the household for these two days, so act like it. Buy groceries, while you’re at it.

Problem Five: Your sister’s son is graduating for high school, and you’re invited to the shindig.

Huzzah, an easy one! Teens are the easiest gift recipients, because all they want is money. Gottsman recommends giving at least $25. Again, if you can afford it, $100 is a very generous gift. If you have the means, you can give even more — go ahead and buy your way to being the Cool Aunt. But make sure you don’t show off too much. Don’t outshine the graduate’s parents — you don’t want to kick off decades of one-upmanship that will end with someone beggaring himself to get a Tesla for a baby.

If you’d rather give a non-monetary gift (again, all the teen wants cash, so do that at your own risk) ask the parents what your nephew needs for his dorm room/gap year/new life as a Snapchat celebrity. Then get them an iPad or a Supreme t-shirt.

Now go forth into Gifting Season armed with knowledge.

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