Ask The Gentleman 2023

Etiquette & Style for the Modern Gent


Being a modern gentleman isn’t just about dressing well and knowing which fork to use at a dinner party, so we asked The Gentleman to chime in and answer your most pressing etiquette questions. Here’s his expert advice on everything from wedding dress codes to first dates.

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I interviewed for a new job this morning that I’m pretty excited about. Should I wait for the company to reach out, or should I follow up (and when)?


Congratulations! The hard part is over, and now comes the waiting game. Fortunately, you still have one more thing in your arsenal that could impress your potential employer: a thank-you note. This email (or handwritten note, if you prefer) should be sent less than 24 hours after the interview; here, you’ll want to express gratitude to the employer for taking time for the interview, as well as restate your interest in the position. Hopefully, the employer gave you a timeline for when you can expect a response from the company – if so, wait for the established timeframe to pass before reaching out yourself. If not, five to seven business days is considered an acceptable amount of time to wait before following up.


What are the guidelines around who should pay on a first date? I’m happy to foot the bill, but don’t want to offend my date!


As the gentleman, you should always pay on the first date, even if she asked you out. When it’s time to pay, pull out your wallet and confidently say, “I’ve got this.” While in theory, your date will smile and allow you to pay without protest, there’s a chance that she will insist on splitting the bill. In this circumstance, you should put up a good fight, but know when to concede. If she’s getting uncomfortable or even irritated by your persistence, it’s probably time to let it go and let her pay her half. On subsequent dates, however, the rules change a bit. Both partners are expected to chip in when it comes to date night, and when a serious relationship develops, it’s helpful to have a conversation about who pays and when.

I got held up at the office and am late for my fitness class. I don’t want to miss out on my workout, but I also don’t want to be disrespectful to my classmates. Any suggestions?

Most gym-goers won’t raise an eyebrow at a participant being five or so minutes late to class, but much more than that and you’ll likely be a disruption. Not to mention, if you find yourself 20 minutes late to an hour-long class, you will have missed the warmup, increasing your risk of injury. To protect yourself, you can perform the moves at a lower intensity, but again, that will probably distract your classmates. So, next time you’re held up at work, just skip the class and find another way to get your heart rate up. Go for a jog, ride your bike, or jump rope in your backyard – the options are endless!


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I fly frequently for work and often get stuck next to a seatmate who likes to chat. How do I discourage conversation without appearing rude?


When you’re already trapped for five hours in a cramped steel machine, not much can make the situation worse than an overly chatty neighbor. But how do you politely communicate your desire for silence without, well, communicating? Your best chance for success is to prevent conversation from the get-go, and “props” are a great way to go about it. Pop in your headphones, read a book, or type away on your laptop to signal to your fellow traveler that small talk is not a part of your in-flight agenda. If you’d prefer to take a more straightforward approach, try something courteous but firm, such as, “Excuse me, if you don’t mind, I’d like to take this time to get some much-needed rest.” Flash a smile for good measure, and you should be well on your way to a peaceful passage … assuming there are no small children around, of course!


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My wife and I were recently invited to a friend’s wedding, but the invitation didn’t mention anything about dress code. I’d hate to show up underdressed (or overdressed for that matter). What should I do?


First, take another look at the invitation. A formal invitation – think swirling calligraphy, traditional wording, and heavy paper – typically signifies cocktail or formal attire, while a more informal invitation – featuring modern fonts and other playful details – might suggest a ceremony that’s more relaxed. The wedding venue is also a major clue; luxe country clubs and grand ballrooms will call for more formal wear, while casual weddings might take place outdoors. Next, if the couple has a wedding website, give it a visit! They may list additional information here such as dress code. You also have the option to reach out to the couple directly. When in doubt, opt for cocktail attire. For men, this looks like a dark suit (gray, black, or navy blue), and don’t forget a tie, which you can always take off if needed. Pass on the khakis unless you’ve confirmed it’s a more laid-back affair.

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