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A Gentleman’s Guide to a Flawless First Date

Planning a date to remember doesn’t have to be hard work. Before you head out to meet that special lady, read this.

July 26, 2018 | By Charlotte Grainger | May contain affiliate links (What's this?)

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There are few things as utterly nerve-racking as first dates. You’ve never met this woman. You know very little about her. And yet, somehow you’re supposed to whisk her off her feet in the hopes that she will fall madly in love with you. It sounds completely insane.

Hey, nobody ever said it was easy. What’s more, as a guy, there’s a whole load of added pressure. Like it or loathe it, social norms dictate that men must take the lead when it comes to dating. Regardless of how much we’ve progressed in recent years, there’s still an underlying expectation that guys will do the majority of the work.

So, where on earth should you start? You’ve come to the right place. Here’s a gentleman’s guide to a flawless first date.

How to Plan Your Date

having drinks on a first date

Spoiler: If you asked your date out, the planning responsibility falls firmly on your shoulders. You can’t just turn up to meet someone without having an idea of what you’re going to do. Before we go any further, you need to forget all the clichés you’ve learned about dating. Contrary to popular belief, the most common date plans are almost always terrible ideas. As a woman, I can tell you that the following date ideas make me recoil out of sheer awkwardness. Here’s why:

‘Let’s head to the movies!’

Taking a woman to the movies might sound like winning idea, right? It’s a classic. However, it’s not always the smartest idea. Think about it. Spending around two hours in sitting next to one another in a dark room—staring forward and not talking—is anything but a recipe for romance. A first date is about getting to know each other and you can hardly do that in silence.

‘Fancy grabbing a bite?’ 

Equally, you shouldn’t go to dinner on a first date as it’s too much of a commitment. Imagine the following scenario. You meet for a fancy dinner date and within minutes realize that you’re not compatible. What do you do? You then have to spend two or three courses making polite chit-chat while both secretly wishing you could leave. It’s a costly waste of your time and your date’s time.

So, what should you do instead? In my opinion, the key here is keeping things light and breezy. On a first date, neither one of you wants to be trapped or to commit hours to something that might not work out. Opt for a super casual meet-up. Grab a quick drink but keep it short and sweet. That way, you can see if  there are fireworks and, if there are, arrange date number two.  And, if there aren’t fireworks, you’ve only wasted around 30-40 minutes on drinks!

3 Things to do Before the Date

giving yourself a pep talk before a first date

#1. Give Yourself a Pep Talk

Confidence is always going to be an attractive quality. I can personally tell you that this is something I find extremely alluring. But hey, you’re only human. We all get nervous and anxious in the lead-up to a date. Despite this, you should avoid letting this perfectly natural human emotion have any effect on how you act during the date.

One of the major things that may concern you is your flaws—you might feel too out of shape, too dull, or not successful enough to be loved. While these thoughts race through your mind, take a step back and exercise a little self-compassion.

Nobody’s perfect and accepting that fact could be the secret to unlocking happiness within your love life. In fact, research has found that those who are compassionate toward themselves have a high chance of making lasting, meaningful relationships. Love yourself and others will follow.

Avoid rushing right out of the door before a date. Take a few moments alone, breathe, and relax. You might find that exercising a little mindfulness or merely repeating some positive mantras helps you get into the right frame of mind. Giving yourself a little headspace is a winning idea and means that you will be cool, calm, and collected when you meet your date.

#2. Consider Who Will Pay

You don’t want to be caught short—neither literally nor figuratively. If you’ve planned a spectacular date for you and your mystery lady, you might want to consider who will be picking up the check. Planning ahead will prevent any awkwardness down the line.

It’s a modern world which might lead you to believe that your date should foot the bill—or, at least, offer to do so. Surprisingly, a huge 72% of women still believe that men should pay on the first date. There’s always the chance that your date will expect you to splash some cash.

Even if that’s not the case, if you’re the one who has arranged the date—i.e. if you asked the woman out—the gentlemanly thing to do is offer to pay for it. You may find that your date wants to go halves on the bill but you should never presume that will be the case.

#3. Do Your Research

Finally, before you walk out the door and meet your date, you need to make sure that you do your research. Knowledge is power.

The chances are that you’ve been talking to this woman for a while before you popped the big ‘Fancy dinner?’ question. That means that you will already have a wealth of resources about her at your fingertips. Go back through your messages and re-read them one last time.

Show that you’ve been paying attention by dropping the information into conversation during the date. For example, if she sent you a text about going to a tennis club, you might say “I know you mentioned you play tennis. How long have you been practicing?” The fact that you remember the small points of conversation will show that you’re attentive and a good listener.

5 Golden Rules for a Winning First Date

man and woman kissing on a first date

But enough about what you should do before the date—let’s take a moment to discuss what you should do once you’re on it. While every woman out there is unique, there are some common guidelines that you should follow to win her over or, at least, have a chance at doing so. With that in mind, here are just five golden rules that will help you along the way.

#1. Dress Well for the Occasion

You’ve heard the stats before—it takes around seven seconds to make a first impression on someone. What’s more, research published in the Social Psychological and Personality Science suggests that people decide whether or not they are attracted to a person win just 33 milliseconds based on merely looking at their face. Remarkable, right?

You’ve got to give yourself a fighting chance here. Focus on looking the part when you walk in the door. Being well-groomed and well-dressed should be your baseline. Women notice the finer details from the minute they see you. Before you head out on the date, make sure that your look ticks these boxes:

  • You’ve shaved and look well-groomed
  • Your clothes fit you well
  • They are suitable for the date

That last point is crucial. You don’t want to wear a dinner suit to a casual drinks meet-up. Equally, if you choose to do an activity (such as bowling) together, you should make sure that your clothing works for that scenario too. Dress well but consider what type of date you’re going on.

#2. Leave Your Smartphone in Your Pocket

Addicted to your smartphone? You might want to cool it. ‘Phubbing’ (phone-snubbing!) is a modern phenomenon in which people ignore their present company in favor of their smartphone. Not only is looking at your phone incredibly rude, but it could also be a deal-breaker for your date.

In fact, 75% of singles say that they are ‘turned off’ when someone answers their phone on a date, according to a survey from Match. Plus, it’s not only speaking on your phone that could be a problem. The same research found that 66% hate texting during a date and 57% are upset if their date so much as reads a text message.

The takeaway is clear—your smartphone does not need to be the third-wheel on your next date. Rather than having it on the table, leave it in your pocket and don’t check it in front of the other person. Instead, give them your full attention. As a woman, if a guy is completely focused on our conversation and seems present, I find it seriously romantic.

#3. Don’t Be Afraid to Flirt (Without Being Creepy)

If things are going well and you feel that all-too-familiar spark, you might want to take things up a gear. The key here is to flirt without being creepy. That in itself is an art form. Coming on too strong is likely to make things intense and, frankly, a little awkward. That’s why you should focus on simple gestures that show your date that you are, in fact, interested in them.

Start small and test the water. You might want to try mirroring your date—i.e. subtly mimicking their body language. When people are attracted to one another, they often do this unconsciously. By affecting it, you’re letting the other person know that you’re attracted to them. Notice how your date reacts to this technique and whether they become warmer or lean in further.

#4. Create Closeness in Your Conversation

What are dates really about? Shockingly, they’re not just a prelude to sex or, worse, an interview for a long-term relationship. No, they’re about getting to know one another and finding out whether you’re compatible. It should go without saying that you should ask your date questions about themselves, but how can you supercharge your conversation?

Self-disclosure—i.e. opening up and telling your date about yourself—could be a quick route to a sense of closeness, research suggests. While you shouldn’t overdo it and spill your entire life story to your date, giving them a few nuggets of information about you is a smart idea. This technique could help your date to feel comfortable around you and want to know more.

Pro tip: Don’t give too much away on a first date. Choose the information that you want to share wisely but always leave your date wanting more. For example, you could tell your date a short but interesting story about your childhood vacations might be a fun way to engage them. However, you might want to leave your underlying mommy or daddy issues out of the chitter-chatter… There’s such a thing as TMI and it’s a real turn-off.

#5. Read the Signs Before You Kiss

To kiss or not to kiss—that is the question! If you’ve had a great date and feel a real connection, you might want to end the night on a high. Before you lean in for that romantic smooch, though, you need to read the signs. Is this what your date really wants? Here are some of the signs that your date is waiting for a quick kiss:

  • They’re lingering when they say goodbye
  • Their body language is positive and pointed toward you
  • They are leaning in… slightly

If all signs are ‘go,’ you might want to lean in for a peck on the cheek. More people are open to kissing on a first date than you might imagine. An overwhelming 64% of singles approve of sealing the deal, according to a survey by Match. It’s crucial that you’re conscious of what the other person wants and that you take things slow.

Equally, you should leave your date wanting more. You don’t want to go ‘all in’ when it comes to the kiss. Instead, give them a polite peck to show them that you had a great time and let them know that you do want to see them again.

Conclusion

Voilà! So long as you follow this guide, you should pull off a successful and memorable first date. It’s important to note that not every date will work out—regardless of how charming and wonderful you may be. Sometimes, things just don’t work out. Sometimes, people are not compatible.

That’s perfectly okay. However, prepping properly for a first date and giving it your best shot is the only way to go. Good luck and happy dating.

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About Charlotte Grainger

Charlotte is a seasoned writer contributing to a range of online publications including Reader’s Digest and Taste of Home Magazine. She’s deeply interested in human psychology, pop culture, and literature. When she’s not typing away, you can find her reading, Netflix-binging, or sleeping.

Reader Interactions

Comments

  1. PJOB says

    July 26, 2018 at 11:19 am

    Anyone – male or female – who has to be told that it’s rude to put your ‘phone out on the table during a date (never mind answering it!) is ignorant to the point of no return. If your ‘phone means that much to you, you should go away and live happily ever after with it.

    Reply
    • Kyle Ingham says

      July 26, 2018 at 6:31 pm

      I agree with you Peter. Yet, it’s amazing how unaware people are of their phone addiction. For many people, the idea of not checking their device for more than 5 minutes makes them physically anxious.

      Reply
    • Di says

      July 26, 2018 at 10:53 pm

      Oh, gosh. I place my phone and keys on the table when sitting down because it gets uncomfortable their staying in my pockets. Really, just suck it up?

      Reply
      • Kyle Ingham says

        July 27, 2018 at 6:22 am

        I think the key point is to make sure the phone is not a distraction for your date or a temptation for you. If you need to, you can keep your phone on the table, but it may be helpful if it’s off to the side, face down, and on silent mode so it doesn’t cause any interruptions the entire date.

        Reply
  2. Dana Woodard says

    July 26, 2018 at 3:20 pm

    What i’m wondering is it seems A Woman seems interested. what is different is how you’ve met the Woman. she’s Online but i haven’t really met Her yet. i first ask open ended questions. i try and get them writing back but they don’t. i don’t ask Her out the first time i see Her Profile. most Women don’t have Much, down making it hard to comment. i asked Her if she would like to meet and have drinks, sometime. i never seem to get a response, from Women. they are always silent giving you the silent treatment. the way it seems they respond, is by viewing you looking at your photo and if they look at it, it says they viewed you. now if they look at your photo long enough it says this person wants to Chat with you. but when you try and ask open ended questions you get NO response, there way of talking it seems is by making it say this person want’s to Chat with you. to me that is not A response. and tells me nothing. i feel there playing games. how do you ask them out Online? what is the best thing to say that get’s them talking? I’ve read things I’ve found on the internet of what to say. this one i found in a video the guy said to say but this might be for in person. Look I’ve enjoyed this conversation this is forward but were gonna go for a drink, sometime i’m going to Grab your Number. so first i asked if she would like to have a drink, sometime and that i loved, Her great energy and i thought she was a Divine,” looking Young Woman. you seem cool. and that she seemed awesome! and said look I’ve enjoyed Chatting with you instead of i enjoyed this conversation with you because she never wrote to me. then said this is forward but were gonna go for a drink, sometime i’m going to grab your Number i look forward to your message. then i wait and she only view’s me long enough it says this person want’s to Chat with you. i maybe should leave my Number with Her. I’ve done it before but i get the same thing that is happening. I’ve tried these different ones i wrote here. How to Ask A Girl out was one of the Headlines. some are for Online and some are for in person. one Woman said one she wrote worked well for Her clients. but so for not for me. so here is the first one I’ve been having so much fun, chatting want to take it offline over a drink, next week?” that is the one that worked well for Her clients who’s A Woman dating couch. “Would you like to have dinner, with me this weekend?” or are you free for a drink, after work this week?” and Ask the Woman in question if she wants to get a drink, on a Saturday.” IT was good to meet with you. which day works to meet for a drink?” one dating coach Corey Wayne said all you have to say is something like this: i Added the “Howdy. “Howdy i really like your profile. i liked what you said and i want to know when your free to meet for a drink?” or you can say Were going to or let’s do this: “Let’s get together for coffee, or drinks, sometime soon. call me old fashioned, but talking in person just seems like a MUCH better way to get to know someone than message online… or “You seem cool, but I’ve found it’s difficult to predict chemistry until you meet someone in person. what are your plans for this weekend?” one Woman wrote a Article saying to ask them out during the week because weekends are valuable to A Woman. i was told not to ask if they would like to go out this week because it gives them a chance to Flake, that you should do that day or the next day. what do you think is best? one dating coach said don’t ask for Her Number you give Her your Number and tell Her to call you. i know Online dating is much different. even if i feel I’ve done things very effectively i get NO response, from A Woman. any help would be great on what exactly what to say? it seems there is NO perfect way to say it. if you watch videos of Men trying to get A Woman’s Number they are very hesitant on giving it out. why come on a dating site, anyway if your not going to respond, to someone. i “Just need a way that works best to ask Her out. Sincerely Dana!

    Reply
    • Kyle Ingham says

      July 26, 2018 at 6:40 pm

      Hey Dana, it’s hard to say what works. Online dating can be tough because you have to try and build a connection through chats/messaging, and like you said, that can be hard. Have you tried “going analog” and doing a speed dating event? Maybe you’d be more in your element connecting with women face to face?

      Reply
      • Dana Woodard says

        July 26, 2018 at 7:22 pm

        HI Kyle i never tried that. although i have seen it done on TV Haha. i wonder where i try that out at? at lease someone can get a Much better sense of who you are. Women just don’t respond, or flake, or are scared, to meet with you. one Woman Dr. Wendy Walsh said you need to make A Woman feel safe, which I’ve tried and did not workout well. i’m not sure how you go about that? she didn’t probably have time on Her Radio show to explain in more detail. one guy i spoke with said who is a Online dating coach said his son works for HINGE the dating App company and said if you strike up a conversation you have better chance at meeting someone. so i guess there is NO correct way how to ask them out Online? i know you must get them talking first. as for you talking about the Phone. i don’t need to worry because i don’t own A Cell Phone only a Landline Phone. i’m kind of old fashioned in that way. i had a Cell Phone but to many things would go wrong so i gave it back. it was threw a plan. it was a cheap Phone. but i like not looking at it because when you focus on the Woman your not distracted and your soul focus is on Her and Women love, when you focus on them. i plan on getting a Phone at some point. thanks for your help. at least i know there is NO exact way of asking them out. but i would love, to know more about speed dating. how i go about doing it.

        Reply

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