How to Be a Better Best Man

Flirt with the mother of the bride, but don’t grind with her.

Troy Patterson.

Troy Patterson

Photo by Christina Paige

Please send your questions for publication to (Questions may be edited.)

Dear Gentleman Scholar,

I had a hunch my best friend of 15 years would ask me to be his best man. The day has come, and I have swiftly become aware of how little I know of what’s expected of me. While other friends assure me that I only need to worry about the bachelor party, some websites insist I should be doing everything from arranging engraved gifts to booking honeymoon hotels. For a modern couple, what is a relatively thoughtful best friend and man and gentleman to do?

Yours truly,

Best Man To Be

Thank you for the question.

As this magazine’s earlier treatment of the topic indicates, it is indeed your duty to organize a bachelor party that’s impossible to forget and traumatic to remember. In this and all other best-manly matters, carry yourself as if you are the sheriff of the good times and the other groomsmen are your deputies. Delegate tasks to responsible (and to proficiently irresponsible) individuals as warranted by events (which may include an actual sheriff’s service of warrants). Heed a wise man’s words regarding the cloud that should cross the groom’s mind in the course of the party: “If I do not get married, I will die within the next year.” 

Between the bachelor party and the wedding weekend, your responsibilities are almost nonexistent. But if the groom is dressing in formalwear for the ceremony, you should assist with matters related to renting a tuxedo, such as convincing him to buy one instead. A tailored evening suit is more physically and mentally comfortable than a rental tux that has serially endured the stresses of prom-night frottage.

At the rehearsal, the bride and groom will merely be practicing their wedding-day roles, but you are debuting your award-winning performance as a local celebrity, a host of honor, and a troubleshooter of all trades. If the wedding is at a vineyard, and if in the vineyard there are snakes, then you will drive out the snakes as discreetly as possible. Flirt with the mother of the bride and any other mother who wants to be flirted with. Build a rapport with the wedding planner. And always and forever OBEY THE BRIDE.

As the rehearsal shades into the rehearsal dinner, leap to address hassles as they arise, like giving directions to the groom’s Nebraskan cousins, who know neither where they are nor how to use Google Maps. Your job is to take some weight off the groom’s shoulders—weight, and dandruff. Stand ready to serve as a valet, a body man, and a personal groomer; the most complete best man tool kit would include a lint brush, a hotel sewing kit, a wine key, a black pen for signing the wedding certificate, backup copies of any original vows or unoriginal Pablo Neruda readings, and a pill case stocked with Altoids and beta blockers.

During and after the rehearsal dinner, begin to scout a suitable venue for the post-reception after-party, be it a sports bar with outdoor seating or a hotel room shared by young colleagues of the groom, provided they demonstrated great talent for rocking out at the bachelor party.

On the day of the wedding, get the groom to the venue on time. Curry favor with the DJ or the band during setup. Deal with the boutonnières. Escort the maid of honor down the aisle. Stand up straight. Grin and bear it through the photo sessions and then deliver to the newlyweds a plate of hors d’oeuvres or at least a stiff drink as they suffer a more protracted ordeal in front of the wedding photographer, who is hard at work stealing the souls that the officiant has so lovingly joined together.

At the reception, deliver a succinct, family-friendly toast and raise a glass to the bride. Do not raise your glass too frequently for a while thereafter: You need a clear head to achieve your dual purpose of ensuring that the bride and groom have the happiest time possible and raising the general level of the party. Your duties may involve delivering checks to vendors, organizing groomsmen to waylay belligerent uncles, and stopping the Electric Slide before it starts. If you see the bride trying to lift a case of wine or anything else heavier than her bouquet, respond by saying, “No, no, no, no, no, no, no, no, no, no, no, no, nooooo.” Make small talk with everyone who seems interesting and when they start being uninteresting, exit the conversation by making a vague reference to your special obligations.

At this point in the proceedings, the show is yours to run. Carry yourself as if your authority is greater that than that of father of the bride, which it is. If this is a catered affair, you may liberate bottles as you see fit. Veto poor decisions at will.

Dance with the bride and with the maid of honor. I disrecommend grinding on the mother of the bride or encouraging flower girls to twerk. If there is going to be a hora, then go round up some chairs, and pitch in with lifting the bride’s 300-pound father. Encourage everyone to dance heartily, but don’t at any point get so lost in the music that you neglect your duties. This may include quietly delivering underarm deodorant to a groom who has gotten lost in the music and, consequently, the funk.

While some sticklers for tradition insist that your job isn’t done until you’ve decorated the getaway car, others, more old-school yet, require you to station yourself outside the bridal chamber and gather proof of consummation. But you say, Best Man To Be, you’re attending to the nuptials of a “modern couple,” so I instead suggest checking in on their progress via Skype, while kicking back on a sports bar’s patio, once again sending the bride your best wishes.

Dear Gentleman Scholar,

I plan on proposing to my longtime girlfriend in the coming year. She isn’t the kind of girl who expects a big rock. She’s said she doesn’t even need a ring, but I find that strange, and I think our families and friends would, too. I’ve heard that the general rule is two to three months’ salary—is that still true? (I’m a graduate student on a tight budget.) Should I forgo the diamond for a sapphire? And should I buy it online, or in person at a jeweler? And what about getting just the right size? There are so many options, and I’m not quite sure how to navigate this process. What’s the right approach?



Thanks for sending your question my way. I hope that asking it has warmed you up to ask further questions of others.

Start by calling your mom. You probably owe her a call anyway. Start with a “Hi, Mom! How are you?” Then cut to the chase: Does she know of any family heirlooms that will suit your purposes? Are there any significant rings or notable gemstones you can lay your hands on without incurring the wrath of a first cousin or disinterring Grandma? Does Auntie Zsa Zsa need some quick cash? If the answer to any of the above questions is yes, then you may already be in good shape.

Whatever the answer, the next move is to call up one or two of the women your beloved would most likely draft as bridesmaids, taking care to steer clear of degenerate blabbermouths. It is not necessary to conduct this mission in complete secrecy—after all, it would be unwise to propose without having discussed marriage in some depth—but nor do you want an adviser who is inclined to spoil all possibility of surprise.

Your girlfriends’ friends are your best guides to her honest desires. Solicit some general thoughts. Keep up your end of the conversation by sharing notes on your GF’s birthstone, her favorite colors, her personal style, and such. Be candid about your budget, and forget the two-to-three months’ salary rule. The correct minimum amount to spend on an engagement ring is enough so that it doesn’t look cheap, and your co-conspirator should be able to help you figure out what doesn’t look cheap. (If you begin to suspect that she herself is a victim of either a cheap sensibility or of expensive tastes, get a second opinion.)

Your future friend-in-law will have some immediate observations, and should be eager to do some recon work. When she has delivered her dossier, you should then start shopping around. Cast a wide net. Maintain an unrushed pace. Regard with open scorn any retailer who gets too pushy—anyone whose hard sell would rate above a 9 on the Mohs scale. And if you are choosing a engagement ring that is not a diamond ring, do not bring the word “engagement ring” into the discussion until after you’ve negotiated a price.

When your window shopping has progressed, take your girlfriend’s friend around to inspect the finalist(s). She will warn you away from potential disasters, ratify sound judgments, and tolerate your second-guessing. After you’ve pulled the trigger, thank her for her time (and earn valuable brownie points) by taking her out for a glass of sparkling wine to celebrate your mutual good taste.

Read more from Slate’s special weddings issue:

Stop the Scourge of Wedding Presents: They’re outdated, inefficient, unfair, and unnecessary,” by Matthew Yglesias. Posted Tuesday, June 11, 2013.

The Long Walk to the Altar: Prudie offers wedding advice on family estrangement, inappropriate toasts, and an extravagant bride, just in time for summer,” by Emily Yoffe. Posted Tuesday, June 11, 2013.

My Big Fat Disney Wedding: I’m a tomboy, not a princess. Here’s why getting married at a huge theme park was a delightfully practical decision,” by Rachael Larimore. Posted Tuesday, June 11, 2013.

This Is the Last Time I Will Ever See You: After every wedding, there is a dear friend who will immediately disappear from your life. And that’s OK,” by David Plotz. Posted on Wednesday, June 12, 2013.

Click Here to RSVP: Online invites are now far better than paper. And yes, you should even use them for your wedding,” by Farhad Manjoo. Posted on Wednesday, June 12, 2013.