A Guide on How to Be a Gentleman on a First Date

In today’s world, first date tips for men can lack a certain sophistication. Online dating is fast-paced and can often seem a bit callous and unromantic. A common question that crops up, especially for over 50s men, is ‘how can I be a gentleman on a first date?’ Here are our eleven top tips on gentleman etiquette and first date advice.

What is a True Gentleman?

The official definition of gentleman according to Merriam-Webster’s dictionary is:

Definition of a gentleman:

Not all of us are so lucky to be born into nobility or royalty, but the aspiration of conducting oneself like you had was incredibly popular for a time. It’s a common cliché in movies and TV that center around the Victorian times (typically centered around the UK) that gentlemen would be acting in the utmost civilized manner. Men couldn’t walk into a room without bowing, removing their hat and offering lengthy introductions to newly met acquaintances.

There’s a real romanticism around the idea of being a gentleman, especially in the modern dating world. First dates make a big impression for further dates and they can be a nerve-wracking experience especially if you’re recently separated, divorced, or widowed. However, the reality is that you’d be hard-pressed to find a woman who would actually enjoy dating someone who rose from their chair and bowed every time they entered/exited a room on a first date. So, we’ve compiled the best tips that marry both worlds. Be a modern gentleman without making your date feel like they’ve walked onto the set of Downton Abbey!

1. How to be a Gentleman: Make an Effort with Your Appearance

You don’t need to turn up in a tuxedo to dress like a gentleman but it’s important to think how you’re presenting yourself to potential partners. Depending on where you go, there will appropriate and inappropriate things to wear on a first date. Most first dates will be for a casual drink or coffee so think about your wardrobe. How to be a gentleman on a first date? Dress smart! A smart shirt, casual jeans, and some nice shoes along with a fresh shower and shave is the more practical first date attire. If you’re feeling a bit lost, or you think your wardrobe isn’t up to scratch, treat yourself and buy some new outfits. If you’re lacking inspiration then pick up some modern men’s magazines and see what tickles your fancy.

2. Picking the Best Place

The first date location is crucial. There’s nothing worse than being excited for a first date only to find out that the person has impulsively booked a skydiving lesson and you’re petrified of heights. That’s an extreme example, but it does show one of the main things men tend to not think about on first dates. Simply, what do they want to do? A gentleman will inquire about their interests, hobbies and cultivate a thoughtful, fun and engaging first date. This means that even if you get the first date nerves, you’ve already shown your prospective partner that you’re a good listener and you care. So, if they mentioned they are interested in art, maybe see if there are any good local gallery exhibitions on.

3. A Great Introduction

One of the most stressful parts of a first date is the first 10 minutes. There are a few ways that a modern gentleman can make this experience better for yourself and your date. First off, you have agreed on your location and the time, make sure you’re there early. If you’re early it shows that you’re conscientious of time and you can also sort out any foreseeable issues i.e. the venue is closed, it’s too busy etc. Another top tip for how to be a gentleman is to make sure your date knows who you are. The classic red rose in the pocket may seem cliché, but it’s also very romantic and practical. There’s nothing worse than entering a crowded cafe trying to spot someone and then awkwardly texting them to ask where they are.

4. Food Choices

If you’re dining out on your first date, then knowing what food to pick is a good mark of how a true gentleman acts on a first date. It’s fairly easy if you use common sense. Keep it simple and manageable. So this means, no ribs covered in sauce, spaghetti getting everywhere and no bloody, rare steak. You don’t have to stick to soups and salads, just be mindful that it’s difficult to talk and wolf down certain meals.

5. Conversational Etiquette

Saying conversation is the most important part of a first date is obvious, it’s essentially the point of the date in the first place. It’s where you find out whether the good time you had messaging back and forth online can be created offline. How then do gentleman conduct a conversation on a first date?

6. How to Treat Others Like a Gentleman

If there was a ‘how to be a gentleman on a first date’ book, treating others with respect would be the most important chapter. It’s a commonly held belief that how you treat others is a reflection on yourself, especially if you’re in a position of superiority. So, when you’re on your all-important first date remember to treat your server with respect and be polite. These manners are a golden rule in the book of modern gentleman etiquette. Even if you feel the service has been bad, try to be polite and don’t moan – gentlemen are always on their best behavior.

7. Courteous and Respectful Physical Interactions

It can be tricky to figure out the level of appropriate intimacy on a first date, especially if you’re trying to date like a gentleman. During the date, if you think a playful hand or arm touch makes sense in context then feel free, but remember a gentleman acts with confidence and not arrogance. Also, remember to not go overboard; if you drop to a knee, pull a Clark Gable eyebrow raise and kiss her hand – chances are you’ll have guaranteed yourself no second date. It’s all about context. What are they talking about? Have the touched you? Is it an intimate setting? Go with your gut.

Read More: What a more in-depth guide on when to kiss her? Check out the expert guide to that first kiss!

8. Paying the Bill

Paying the bill is potentially the most controversial topic to tackle when it comes to ‘how to be gentlemen on the first date’. There are many opinions on this seemingly simple issue, particularly if you’re trying to be a modern, forward-thinking gentleman. Psychology Today looked at the reasoning and background behind the ‘who pays for the date’ debate. According to them, heterosexual couples still follow a fairly traditional script during dating and both men and women expect the man to pay for the date. However, they also said that this can be very difficult on a first date if one of the partners wants to split the bill. Playing it safe, we recommend trying a wry and flirty comment like ‘I’ll get this and you get the next one?’ This insinuates that there’ll be a second date. Simple, charming and also demonstrating an understanding of the tricky nature of paying for a date.

9. Saying Goodnight

Ah, this is it.

The classic movie cliché, seeing them off at their doorstep after a perfect first date. So, how does a true gentleman deal with this scenario? First off, make sure your date gets home safe, which could mean walking them home or giving them a lift. Next, a goodbye at their front door. Now, here is the perfect opportunity for a goodnight kiss. But how do you tell if it’s the right time? Simple – just ask.

Ask them, did they have a good time? Would they like to see them again? Remember, a gentleman acts with a quiet and charming confidence; asking your date outright is a good way to show your interest. If they say yes, then a hug and a peck on the cheek (or lips if you feel it’s warranted) is perfectly fine. Anything more than that on a first date can get too complex. Better to show them that you’re sincere in wanting to get to know them and decline an invitation inside, and instead book a second date there and then.

10. Following Up

Deciding when you should contact someone after a date seems like a young person’s problem but it’s probably the main issue that younger and older dating share in common. A gentleman should bookend a date satisfyingly. The next morning, text your date and express your enjoyment on the date and ask if they’d like to do it again. If you discussed mutual interests on the date like the theatre or the cinema, suggest that as the follow-up. This little personal touch will show that you paid attention on the date and is an elegant move, perfect for a gentleman.

11. How to be a Gentleman From Now On

Ready to date but can’t find a partner? Our tips on how to be a gentleman on a first date is chock-full of advice, but you need to get the date first right? Don’t worry, modern gentlemen are welcome on SilverSingles. The dating website especially designed and created for adventurous and companion-seeking singles over 50. We help you find the perfect match and best of all, we do all the heavy lifting! Just take our in-depth personality test and we’ll start sending you 3-7 matches per day. So, what are you waiting for? Sign up today.