Be a Gentleman – 7 Dating Tips So You Stand Out on a Date

Although gentlemanly behavior may be endangered in the modern world, it is still craved by most women. As fewer men adopt the skills of suave, this creates an enormous opportunity to stand out above the rest with just a little thought and effort. 

In this article learn

  • Aspects of modern social culture eroded gentlemanly behaviour
  • Small actions can reap strong benefits when acting like a gentleman
  • The 7 steps to sweeping her off her feet

The dating dance has become increasingly complicated as gender roles dilute and the method by which we meet each other becomes more disposable. The dating waters have never been more treacherous. Getting from a dating app to a serious relationship seems insurmountable. But that’s where a few dating tips and guidelines put you at a huge advantage over the competition. 

As the modern woman stakes her claim on equality, fights for the parody of pay and demands #MeToo within the workplace, she feels compelled to ask for less from the men in her life. Gentlemanly behaviour becomes confusing as she wonders if it somehow reduces her power if she is taken care of or doted on in any way. Likewise, the redundant gentleman will park his manners to respect her gender equality. The problem with this strategy from both sides is that it neutralises the gender roles which can interrupt the chemistry between the two. The man chooses to remove the rules that would give him purpose but has nothing to replace them with, leaving the dynamic between the two more mateship than courtship. Somehow they must then make the leap to sexual chemistry which very often falls flat. To make matters worse, as time progresses, young up-and-coming men are not even being taught the skills of their fathers or older peers and the art of being a gentleman is becoming endangered. 

Romance will never go out of style!

At the same time, the disposable dating app culture has harmed finer behaviour. There is little or no community connection between men and their prospective date which means they do not feel accountable in any way towards the women. And if they don’t get their reward of sex from as little effort as possible, there is always a seemingly endless supply of women waiting on their phones. 

This perfect storm against the gentleman presents an incredible opportunity for any man who cares to sit up and take notice. All the social and technological change in the world does not take away the power of gentlemanly behaviour. Whether it’s their Hollywood fantasy or something far more natural & primal, women respond positively to gender role distinction during the date. In short, being more masculine enables them to be more feminine. This gender structure stimulates sexual chemistry and helps enhance the romance of the connection.
Even if we continue to debate this gender role issue, in the end, gentlemanly behaviour has a power that no one can dispute. No matter how socially advanced they would think they are, the feeling of being special equates to the universal human need of significance which every person on the planet is drawn to.
I deal with some of the most driven, successful women in the world and one thing remains. Even though women are empowered and independent these days, a woman likes to be treated like a lady. Sometimes, men are hesitant about how will they act or what to do to show that they care.

Simple dating tips to help you stand out among men:

Plan the date

Plan a date carefully before you go out, make reservations, and ensure the venue is comfortable and quiet enough for you to talk and enjoy each other’s company. Women like a man who takes charge and makes decisions. Even the most ‘type A female’ wants to feel special and making a little effort before the date will start that ball rolling.

Dress up

I am amazed when I go out to a nice restaurant. My partner and I have both made an effort. He is well-groomed, smells amazing and is stylishly dressed. I love that he has made an effort. I return in kind and it enhances the occasion. But we show up at the restaurant and I see men dressed in garb that would barely be acceptable at the local pub. Scruffy hair, ungroomed beards, dirty old sneakers. WHAT ARE THESE MEN THINKING? And, quite often the woman is beautifully dressed undoubtedly leaving her feeling like she has overdone it or that he doesn’t give a shit. A gentleman takes the time to prepare himself for the date. The effort he makes results in her feeling special, not to mention more attractive to her. Remember, a women’s sexual drive is not a light switch, it’s a slow burn that starts with her liking what she sees. 

Be Romantic

Consider thoughtful gestures. Ask her if the temperature is fine and offer her your jacket if it’s cool outside. At the end of the night remember to walk her to her car or ensure she is safely in a cab. These are simple, old-fashioned gestures that show you are attentive and considerate.

Remember the Classics

The classics are everything you’ve seen in old movies- open the door for her, always let her go before you, stand when she does, gently guide her through awkward spaces with a light touch at the small of her back or offer your hand when leading her through a crowd. Pull out her chair and pour her wine and water. Finally, settle the bill discreetly. If she’s traditional she will love you for it. If she’s a modern woman, she’ll likely pay for your next date… which you will graciously accept.

Compliment her

Let her know you think she has beautiful eyes or a lovely smile. Perhaps her dress, her shoes, her hair, her perfume. A modern gentleman notices these things. Later in the date, find some things that go beyond appearances to comment on. Her courage, her candour, her grace, her perspicacity for a certain subject, her passion for a particular pursuit. When you compliment a woman on these things she feels “seen”. I can’t begin to tell you how powerful this is as a first impression.  

Lead but don’t dominate

Part of being a gentleman is balancing taking the lead with respecting her as a modern woman. If your gestures are too blatant it can seem pushy or ignorant. Make decisions on her behalf but check in with her about them. For example, “I chose the table on the balcony because it’s a beautiful night, are you happy to be outside?” Here you’ve made a decision yet checked in with her. This is super effective. If you’re at dinner or at the bar, ask her what she would like, make suggestions, and then once she chooses, offer to do the ordering. 

Be thoughtful and considerate

Always be thoughtful of her needs and you will win her heart.  A true gentleman is interested in the comfort of others and will plan thoughtfully to anticipate her needs such as arranging a date near home or finding out her favourite food or activity from a friend. Ask meaningful questions and listen carefully to her answers. Let her know that you’re interested in discovering what lights her up. Use your own creativity to think of unique and unexpectedly thoughtful things you can do to express your care. For example, you could take her on a picnic at dusk, sailing around the harbour or if she is sporty or adventurous you could take her scuba diving!

In a modern world where women fight to be equal, at the same time facing increased disrespect through the dating app culture, a man who shows he can be a gentleman can be incredibly effective. I speak to many women who actually feel that they’ve lost hope in finding (what they refer to as) a real man. The fact that the bar has been lowered so much by the app culture whilst gender equality has thrown men for a six, now, while other men struggle, just a few small gestures can have you rise above the crowd. 

Take the time to consider these tips and implement them into your dating strategy. Your enthusiasm for the woman you have just connected with will likely be returned in spades.

About Trudy Gilbert of Elite Introductions:

Known as Australia’s Millionaire Matchmak­er, Trudy Gilbert has been featured on national TV and radio. She is a sort after speaker, has published her tell-all book on dating- 49 Secrets of an Elite Matchmaker and now runs an online dating and relationship training portal at

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