FIRST DATE GUIDE FOR A GENTLEMAN

I was thinking the other night about the first date. The experience, that no matter what your age, your confidence level or experience, always draws butterflies. The pressure of the first impression. The desire to look and feel your best, and the preparation and care you take with grooming and wardrobe. Before the date even begins, you may play the potential scenes in your mind like a movie. I’ve had a lot of first dates. An experience where the challenge and opportunity intermingle fluidly, teasing you.

As opinionated as I am, I will also share my thoughts with you on what makes a great first date because after all, “the wise warrior avoids the battle.” First dates are not about seduction. It is an opportunity to road test your emotional intelligence through listening, empathy, sharing.

Dress For The Personality of Your Date.

If you are going on a first date, presumably you have conversed with your date and have sense of her style and personality. Unless you are attended a formal event, mirror her style with your dress sense. I went on a date once with a guy who peacocked his suit out to the point where I felt it was chaotic, and it turned me off. There will be plenty of time, to reflect your personality through your wardrobe later on but work the K.I.S.S method and you may just land one at the end of the night!

Keep it To a Two Drink Maximum.

Trust me. I know you might be nervous and a cocktail will calm those nerves, but keeping your whits about you is key. Another personal story…Well, I will save that for another day, but let’s just say that alcohol impairs judgement which can sometimes make for a night with too much vibrancy than one can handle. I understand you may both be oenophiles and sharing a bottle of wine, may just be necessary. I say hold off until date the second or third date. The thrill of the first date is whether or not there will be more to follow…so, keep it to two.

First Date Conversation. How to Get to Know Someone.

Assuming the conversation that led to a first date was charming and interesting, don’t overthink. I suggest have a few funny stories, interesting questions, or curious observations. I want to know know that you are intellectually curious. The ability to have depth but also laugh at yourself, or find humor in a situation, strikes the perfect balance. LISTEN intently. The best conversation often flows from the questions and observations of your date. Remember, its a volley. The most annoying thing is when conversation becomes an interview. You ask the questions, they answer and don’t attempt to want to know about you.

To Pay or to Split. The Bill Conundrum.

As far as I am concerned, the man should always pay on the first date. I like to be courted. I think a man paying show’s respect and deference to the time spent in a woman’s company. Call me traditional. I can tell you that many of my friends who say it doesn’t matter, find “going dutch” to get irritating. Its a small investment for the potential that exists.

The Perfect Ending.

As someone who builds connection for a living, there are levels of it, and sometimes, you find that no matter how you try, it just doesn’t feel natural. If you are feeling it, lean in and be sure to ask for a 2nd date at the end of your first. I think by date #3, you will know where things are going. When you kiss, be adaptable to her style. I’ve had my share of bad kissers and that actually kills my impression.

First dates are an adventure! Relax into it and enjoy the journey.