Ask The Gentleman 2025

Being a Southern 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 phone usage in the workplace to difficult conversations with loved ones.

football ballI volunteered to host Sunday football watch parties at my place, and we usually have plenty of food and drinks. But last time, things got a little rowdy, and one of my friends left a stain on my brand-new furniture. How can I ask him to be more mindful without coming off as uptight?

It’s all in the delivery. Instead of calling him out in front of everyone (which could embarrass him or cause him to get defensive), pull your friend aside or give him a quick call before the next game. Let him know how much you enjoy having him over and that you’re glad to host, but mention that your furniture is new and you’re trying to keep it in good shape. A light, casual request for him to be a little more careful with food and drinks should get the message across without making things awkward. Or, if you’d rather not single anyone out, you can give the whole group a friendly reminder before the next hangout, so it feels like a general ground rule instead of a personal critique.

boat wheelI recently took my wife’s side of the family out on the lake and they had a great time, but now my brother-in-law keeps asking if he can borrow my boat. I don’t feel comfortable lending it to anyone, but feel awkward saying no since he’s family. Do you have any advice on how to navigate this?

While I can’t blame the guy for trying, a boat is a major investment and it’s completely reasonable to be protective of something so valuable. What your brother-in-law may not realize is that there are insurance requirements, liability concerns, and potential costs that come with someone else operating it, and if anything went wrong, it could create both financial and family stress. It’s best to be both honest and kind. Let him know that while you love having him out on the water, you’ve decided not to loan the boat to anyone – even family – for those reasons. You can soften the “no” by inviting him to join you for another outing soon. This way, you protect your boat and reassure your brother-in-law that you’re looking forward to making more memories together.

book clubMy girlfriend organized a book club with some of her friends and is really excited about it. She invited me to participate in the monthly meetups, but I don’t have any interest in the genre they read and would feel out of place as the only man in attendance. How can I let her know without upsetting her?

Her excitement likely comes from wanting to share something fun with the people she loves. A good approach is to gently explain that, while you want to spend quality time with her, this particular group might be better suited for just her and her friends. To show you’re making an effort, you could suggest a compromise: maybe the two of you could join a different club together or start an activity you both enjoy, perhaps even with other couples. Framing it with love and offering an alternative makes it clear you’re not dismissing her enthusiasm, you’re simply finding a way to connect that feels enjoyable for both of you. The goal is still the same – spending meaningful time together and strengthening your relationship.

hand and phoneI’m a little unsure about what’s considered proper cell phone etiquette in professional settings. Is it alright to check your phone at networking events, or should I keep it put away? What can I do to avoid reaching for it when the conversation lulls?

Networking events can certainly feel intimidating, especially if you’re new to the scene, and it’s natural to want to retreat to your phone in those moments. However, in professional settings, it’s best to keep your phone tucked away and give your full attention to the people around you. This signals respect, interest, and professionalism. I would even suggest silencing your phone and resisting the urge to check it. If you must take an important call or respond to something urgent, step aside politely so it doesn’t disrupt the flow of conversation. As for those lulls, challenge yourself to lean into the pause rather than escape it. Ask open-ended questions, comment on the event itself, or invite someone nearby into the conversation. Breaking out of your shell professionally takes time, but choosing genuine connection over distraction will strengthen your confidence and leave a lasting impression.

Help! My wife and I’s 30th anniversary is this weekend, and it completely slipped my mind. Should I try to put something together last minute or be honest and plan something thoughtful for another day?

Hey, it happens. Sometimes life just gets busy! Ultimately, you know your relationship best. If you think your wife would be upset at something planned with short notice, opt for the truth. Have an open conversation about how much she means to you and explain that while you don’t have something set for this weekend, you want to create a celebration that’s truly special. Another option is to surprise her with a thoughtful placeholder, such as tickets to an upcoming show, a reservation at her favorite B&B, or plane tickets to a bucket list destination. That way, she still receives the gift on your actual anniversary, while the celebration comes later. No matter what you choose, the key is showing her your love and appreciation. After all, anniversaries are less about the date and more about celebrating the life you’ve built together.

– The Gentleman

Get Free Digital Copies of CityScope® Emailed to You!