Gentlemen Rules for Dating By: Jim Gandolf

I am helping my son, to whom I have raised to be a Gentleman in today’s world! 

Jim Gandolf

(Author & Poet)

WMA Banking & Finance 

Bonded & Assured 

KOJC

G.U.T.

JGM

Being a gentleman in dating is about showing genuine respect, consideration, and integrity. While some traditional gestures remain, the focus in modern dating is on being a thoughtful, emotionally intelligent, and reliable partner.

Here are the key rules for dating as a gentleman, categorized for clarity:

1. Planning and Preparation

 * Take the Initiative and Plan Ahead: Don't "wing it" for a first date. Suggest a specific time, date, and activity (e.g., "Would you like to go for coffee at The Corner Cafe this Saturday at 2 PM?"). Make reservations if necessary. This shows you value their time and are serious about the date.

 * Be Punctual: Arrive on time, or a few minutes early. If you are unavoidably delayed, call or text immediately to let your date know and sincerely apologize.

 * Present Yourself Well: Dress appropriately for the venue, ensure you are well-groomed, and your clothes are clean and ironed. Making an effort shows respect for your date.

2. Courtesy and Chivalry

 * Offer to Pay: A gentleman traditionally pays for the first date. If your date offers to split the bill, you can politely say, "My treat this time, but you can get the next one," which also sets the stage for a second date. Always pay graciously.

 * Be a Guardian of Comfort and Safety:

   * Doors: Open doors for your date (car, restaurant, building).

   * Seating: Pull out her chair for her to sit down.

   * Walking: When walking on the sidewalk, walk on the side closer to the street.

   * Pickup: If you are picking her up, walk to the door to greet her—do not just honk or text from the car.

   * End of Date: Ensure she gets home safely, whether by walking her to her door, waiting until her ride-share arrives, or driving her yourself.

 * Treat Service Staff Well: Be unfailingly kind, polite, and respectful to waiters, bartenders, and all service staff. How a person treats those they don't need to impress is a true measure of their character.

3. Conversation and Attention

 * Give Her Your Full Attention: Put your phone away—on silent, and out of sight. The only exception is an absolute emergency. 

Constantly checking your phone signals that you are bored or that something else is more important than your date.

 * Be an Active Listener: Ask open-ended questions and genuinely listen to the answers. Show sincere interest in her life, hobbies, and perspectives. Conversation should be a two-way street; avoid monopolizing the talk by speaking only about yourself.

 * Be Positive and Respectful:

   * Compliments: Offer sincere compliments, focusing on her appearance and her character or intelligence.

   * Avoid Negativity: Do not speak ill of ex-partners, friends, family, or co-workers.

   * Sensitive Topics: For early dates, it's often wise to steer clear of heavy topics like politics, religion, or your entire relationship history, unless your date initiates them.

 * Maintain Eye Contact: Confident, steady eye contact shows you are engaged and present.

4. Integrity and Respect

 * Be Yourself (Authentically): Be honest about who you are and what you are looking for. Pretending to be someone you're not is a disservice to both of you.

 * Respect Her Boundaries: Pay attention to her comfort level (verbal and non-verbal cues) and never pressure her for anything. A gentleman understands that time with her is the goal, not a means to an objective.

 * Follow Up: After the date, send a brief message to thank her for the evening and express that you had a good time. If you want a second date, ask for one in a timely manner (usually the next day).

 * Be Gracious in All Outcomes: If you decide not to pursue a second date, let her know politely and respectfully. If she is not interested in seeing you again, accept her decision gracefully without dwelling on it or playing games.

Jim Gandolf 

©️10132025