First Date Advice For Men

#Dating + Relationships

To any guy reading this: I’m just the liaison between you and 24 ladies that have generously provided you with 6 simple yet crucial pieces of advice for any and ALL first dates, so don’t kill the messenger! Here are the top pieces of advice mentioned— AKA, this is what we want and don’t want you to do. You’re welcome ;).

Humor Us

WE LOVE FUNNY. You basically already have an advantage over the mundane majority if you make us LOL. Like, keep us lol-ing, please. The best way to be funny is by being yourself, quirks, goofiness and all. I want to state that this was the most common advice given by women on this topic. If you don’t think you’re funny, maybe try doing some sort of activity/game/arcade-type setting where you can both laugh at and tease each other. Being able to make us laugh is so endearing and it peaks our intrigue so much more.

Pay For The Date

If you didn’t catch my article on When Women Should Split the Tab, please do yourself a favor and read it ASAP so you stop fcking up your love life. To any lady reading this right now, that goes for you too! You’ll find some solid information in there. Ok, let’s get back on track!

I’m going to make it reeal simple for any little boys kicking and screaming right now. If you ask/let a lady YOU invited on a date to pay for half of it, you are either intentionally friend-zoning her or need to brush up on your courting skills. I’m going to offer to pay my half every time because I was raised with manners, but if a boy (because a man wouldn’t let me, lol) asks or lets me split the tab on the first date, I will assume he wasn’t raised with proper manners. You (most likely) invited me. I didn’t plan on dipping into my money for a date of your choosing. My investment is my time in this situation.

Other investments not mentioned: Depending on how interested I am in you… Shellac mani & pedi… $70. Blowout… $60. New top… $50. My personal inve$tment + my time = more than our first date, kk?

You’re triggered? Well then, maybe don’t invite someone to a place where you have to spend your money (if you are expecting to split the tab - CHIVALRY IS NOT DEAD). If you don’t want to spend your money, honey, there are other ways to be charming. Grow your own fruits and veggies and take the lady out for a picnic with your homemade Sangria (I get it, it’s a long-play, but honestly I’d be impressed).

Ask Questions

Engage to get engaged. I’m kidding, RELAX. But really, engage. Ask questions to get to know each other and see if you actually like one another. If you catch yourself doing most of the talking, I want to congratulate you for having enough self-awareness to realize you’re a Chatty Cathy (I really do mean this). Self-awareness is something you’ve probably heard me talk about on the blog and how I believe it should be on everyone’s list of core-values. Self-awareness harnesses your ability to consciously halt certain behaviors that negatively affect you and those close to you.

Here are some questions that will get you both in a good flow of conversation. Asking genuine questions will make her feel seen, heard and appreciated (yes please).

  • What Was The Last Book You Really Got Into?
  • Among Your Friends, What Are You Best Known For?
  • How Many Siblings Do You have? - What Are They Like? or What Was It Like Being An Only Child?
  • What Would Be Your Dream Job?
  • What’s The Silliest Fear You Have?
  • What’s Your Favorite Movie & Why?

Don’t Talk About Your Ex

The only time your ex should be brought up in conversation is NEVER. Kidding, sometimes the exes come up if people are having deep conversations which I can appreciate but there is no reason to stay in the past. Look across, you’re with someone new. Don’t waste each other’s time. Be fully present, it will allow you to give this an honest shot. Generally speaking, talking about your ex, especially if you’re talking about how shitty of a partner they were — is VERY UNATTRACTIVE and says more about you than what you’re saying about them. Leave the past where it belongs, in the past.

Don’t Act Like You Don’t Care

Multiple women mentioned they’ve gone on first dates where the guy has acted extremely indifferent about being on the date. In my opinion, this is either a way of suppressing this guy’s nervousness so they project the opposite (not caring), or it means that the guy actually doesn’t care and is uninterested. In which case, why TF is he on this date in the first place?! They’re silly (I really want to use another word but I’m trying to tone down the sass) for wasting each other’s time and energy.

SO! Bring some energy— genuine interest into conversations, laugh and smile! If that means having to take a siesta before the date to fully be present, please do so. But most importantly, don’t go on a date you don’t care about. That’s just stupid, isn’t it?

If it’s a nervousness issue… RELAX. Go into the date as if you were rekindling an old friendship. Here is the most important thing… tie ZERO expectations to the outcome. A lot of people view things in black in white, good and bad, success and failure. This could really fck things up for you. I cannot stress enough that if you view dates in a “success / failure” outcome, you will be extremely susceptible to disappointment and anxious thoughts. Try to shift your perspective into thinking that you just had a great or not so great experience with someone. If it’s the latter, thats ok. They are not your person and you’ve just weeded out the wrong partner and are now closer to finding the right one ;). There are 7 billion people in this world, you’re going to hit it off with someone, this I promise you.

Don’t Try to Sleep With Her

Various women responded to my question by asking me to tell you boys to not even try to hit a home run on the first night. I understand that some ladies love playing baseball and have been on loads of teams, but generally speaking… if you try to sleep with a lady on the first night, it shows your true intentions and sort of ruins the way we felt about you. Some women need to establish an intellectual/emotional bond before they can deeply connect on a physical level. The only way to create an emotional/intellectual bond is if she feels seen, heard and appreciated through genuine interest and consistency.

If you only have one motive such as looking for some capital-F-fun, vocalize that. We actually really appreciate honesty (no, this isn’t a trap), and will find it attractive that you know what you want and the fact that you have enough self-awareness to realize you’re only looking for some capital-F-fun at the moment. Being honest from the beginning is so respectable and easy to do since there are no strong feelings yet involved. If you can’t be honest, work on your transparency/communication skills and save everyone time, energy and feelers.

Other Tips For A First Date

  • As a gentlemen, walk on the side of her that is closest to the street
    This is the simplest yet most thoughtful thing a man can do. It’s my personal favorite. Only two men have ever done this for me (every time) and it made me feel so protected by them. Hello, primal needs. Guys, we are no longer talking about surface-level attraction, we are talking about biological wiring, and that shit wins, every time.
  • Stay off your phone
    Unless it’s an emergency or something urgent.
  • Try not to get too intoxicated
    I get you might want to calm your nerves or enhance the experience, but going overboard could really fck things up for you.
  • Be on time
  • If she’s cold, offer her your jacket
  • Start taking it off before she even accepts or denies your offer. ACTIONS > WORDS.
  • Open doors for her
  • Text her that you had a nice time with her at the end of your date
    Only do this if you actually had a good time, lol. If you didn’t and don’t plan on seeing her again… you can wait until she reaches out and politely tell her you are not interested.
  • Do not, I repeat DO NOT go to the movies on the first date
    Dinner and a movie? How cliché. How about dinner and a stroll? Dinner and an activity where you can actually chat and get to know one another? Capeesh?

Ok! I’m done doing God’s work here. Until next time ;)

Stephanie Daily

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To any guy reading this: I’m just the liaison between you and 24 ladies that have generously provided you with 6 simple yet crucial pieces of advice for any and ALL first dates, so don’t kill the messenger! Here are the top pieces of advice mentioned— AKA, this is what we want and don’t want you to do. You’re welcome ;).

Humor Us

WE LOVE FUNNY. You basically already have an advantage over the mundane majority if you make us LOL. Like, keep us lol-ing, please. The best way to be funny is by being yourself, quirks, goofiness and all. I want to state that this was the most common advice given by women on this topic. If you don’t think you’re funny, maybe try doing some sort of activity/game/arcade-type setting where you can both laugh at and tease each other. Being able to make us laugh is so endearing and it peaks our intrigue so much more.

Pay For The Date

If you didn’t catch my article on When Women Should Split the Tab, please do yourself a favor and read it ASAP so you stop fcking up your love life. To any lady reading this right now, that goes for you too! You’ll find some solid information in there. Ok, let’s get back on track!

I’m going to make it reeal simple for any little boys kicking and screaming right now. If you ask/let a lady YOU invited on a date to pay for half of it, you are either intentionally friend-zoning her or need to brush up on your courting skills. I’m going to offer to pay my half every time because I was raised with manners, but if a boy (because a man wouldn’t let me, lol) asks or lets me split the tab on the first date, I will assume he wasn’t raised with proper manners. You (most likely) invited me. I didn’t plan on dipping into my money for a date of your choosing. My investment is my time in this situation.

Other investments not mentioned: Depending on how interested I am in you… Shellac mani & pedi… $70. Blowout… $60. New top… $50. My personal inve$tment + my time = more than our first date, kk?

You’re triggered? Well then, maybe don’t invite someone to a place where you have to spend your money (if you are expecting to split the tab - CHIVALRY IS NOT DEAD). If you don’t want to spend your money, honey, there are other ways to be charming. Grow your own fruits and veggies and take the lady out for a picnic with your homemade Sangria (I get it, it’s a long-play, but honestly I’d be impressed).

Ask Questions

Engage to get engaged. I’m kidding, RELAX. But really, engage. Ask questions to get to know each other and see if you actually like one another. If you catch yourself doing most of the talking, I want to congratulate you for having enough self-awareness to realize you’re a Chatty Cathy (I really do mean this). Self-awareness is something you’ve probably heard me talk about on the blog and how I believe it should be on everyone’s list of core-values. Self-awareness harnesses your ability to consciously halt certain behaviors that negatively affect you and those close to you.

Here are some questions that will get you both in a good flow of conversation. Asking genuine questions will make her feel seen, heard and appreciated (yes please).

  • What Was The Last Book You Really Got Into?
  • Among Your Friends, What Are You Best Known For?
  • How Many Siblings Do You have? - What Are They Like? or What Was It Like Being An Only Child?
  • What Would Be Your Dream Job?
  • What’s The Silliest Fear You Have?
  • What’s Your Favorite Movie & Why?

Don’t Talk About Your Ex

The only time your ex should be brought up in conversation is NEVER. Kidding, sometimes the exes come up if people are having deep conversations which I can appreciate but there is no reason to stay in the past. Look across, you’re with someone new. Don’t waste each other’s time. Be fully present, it will allow you to give this an honest shot. Generally speaking, talking about your ex, especially if you’re talking about how shitty of a partner they were — is VERY UNATTRACTIVE and says more about you than what you’re saying about them. Leave the past where it belongs, in the past.

Don’t Act Like You Don’t Care

Multiple women mentioned they’ve gone on first dates where the guy has acted extremely indifferent about being on the date. In my opinion, this is either a way of suppressing this guy’s nervousness so they project the opposite (not caring), or it means that the guy actually doesn’t care and is uninterested. In which case, why TF is he on this date in the first place?! They’re silly (I really want to use another word but I’m trying to tone down the sass) for wasting each other’s time and energy.

SO! Bring some energy— genuine interest into conversations, laugh and smile! If that means having to take a siesta before the date to fully be present, please do so. But most importantly, don’t go on a date you don’t care about. That’s just stupid, isn’t it?

If it’s a nervousness issue… RELAX. Go into the date as if you were rekindling an old friendship. Here is the most important thing… tie ZERO expectations to the outcome. A lot of people view things in black in white, good and bad, success and failure. This could really fck things up for you. I cannot stress enough that if you view dates in a “success / failure” outcome, you will be extremely susceptible to disappointment and anxious thoughts. Try to shift your perspective into thinking that you just had a great or not so great experience with someone. If it’s the latter, thats ok. They are not your person and you’ve just weeded out the wrong partner and are now closer to finding the right one ;). There are 7 billion people in this world, you’re going to hit it off with someone, this I promise you.

Don’t Try to Sleep With Her

Various women responded to my question by asking me to tell you boys to not even try to hit a home run on the first night. I understand that some ladies love playing baseball and have been on loads of teams, but generally speaking… if you try to sleep with a lady on the first night, it shows your true intentions and sort of ruins the way we felt about you. Some women need to establish an intellectual/emotional bond before they can deeply connect on a physical level. The only way to create an emotional/intellectual bond is if she feels seen, heard and appreciated through genuine interest and consistency.

If you only have one motive such as looking for some capital-F-fun, vocalize that. We actually really appreciate honesty (no, this isn’t a trap), and will find it attractive that you know what you want and the fact that you have enough self-awareness to realize you’re only looking for some capital-F-fun at the moment. Being honest from the beginning is so respectable and easy to do since there are no strong feelings yet involved. If you can’t be honest, work on your transparency/communication skills and save everyone time, energy and feelers.

Other Tips For A First Date

  • As a gentlemen, walk on the side of her that is closest to the street
    This is the simplest yet most thoughtful thing a man can do. It’s my personal favorite. Only two men have ever done this for me (every time) and it made me feel so protected by them. Hello, primal needs. Guys, we are no longer talking about surface-level attraction, we are talking about biological wiring, and that shit wins, every time.
  • Stay off your phone
    Unless it’s an emergency or something urgent.
  • Try not to get too intoxicated
    I get you might want to calm your nerves or enhance the experience, but going overboard could really fck things up for you.
  • Be on time
  • If she’s cold, offer her your jacket
  • Start taking it off before she even accepts or denies your offer. ACTIONS > WORDS.
  • Open doors for her
  • Text her that you had a nice time with her at the end of your date
    Only do this if you actually had a good time, lol. If you didn’t and don’t plan on seeing her again… you can wait until she reaches out and politely tell her you are not interested.
  • Do not, I repeat DO NOT go to the movies on the first date
    Dinner and a movie? How cliché. How about dinner and a stroll? Dinner and an activity where you can actually chat and get to know one another? Capeesh?

Ok! I’m done doing God’s work here. Until next time ;)

Stephanie Daily

Articles You Won't
Mark As Junk

Never miss a new article!
We respect your privacy and will never distribute any information submitted on this form.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

To any guy reading this: I’m just the liaison between you and 24 ladies that have generously provided you with 6 simple yet crucial pieces of advice for any and ALL first dates, so don’t kill the messenger! Here are the top pieces of advice mentioned— AKA, this is what we want and don’t want you to do. You’re welcome ;).

Humor Us

WE LOVE FUNNY. You basically already have an advantage over the mundane majority if you make us LOL. Like, keep us lol-ing, please. The best way to be funny is by being yourself, quirks, goofiness and all. I want to state that this was the most common advice given by women on this topic. If you don’t think you’re funny, maybe try doing some sort of activity/game/arcade-type setting where you can both laugh at and tease each other. Being able to make us laugh is so endearing and it peaks our intrigue so much more.

Pay For The Date

If you didn’t catch my article on When Women Should Split the Tab, please do yourself a favor and read it ASAP so you stop fcking up your love life. To any lady reading this right now, that goes for you too! You’ll find some solid information in there. Ok, let’s get back on track!

I’m going to make it reeal simple for any little boys kicking and screaming right now. If you ask/let a lady YOU invited on a date to pay for half of it, you are either intentionally friend-zoning her or need to brush up on your courting skills. I’m going to offer to pay my half every time because I was raised with manners, but if a boy (because a man wouldn’t let me, lol) asks or lets me split the tab on the first date, I will assume he wasn’t raised with proper manners. You (most likely) invited me. I didn’t plan on dipping into my money for a date of your choosing. My investment is my time in this situation.

Other investments not mentioned: Depending on how interested I am in you… Shellac mani & pedi… $70. Blowout… $60. New top… $50. My personal inve$tment + my time = more than our first date, kk?

You’re triggered? Well then, maybe don’t invite someone to a place where you have to spend your money (if you are expecting to split the tab - CHIVALRY IS NOT DEAD). If you don’t want to spend your money, honey, there are other ways to be charming. Grow your own fruits and veggies and take the lady out for a picnic with your homemade Sangria (I get it, it’s a long-play, but honestly I’d be impressed).

Ask Questions

Engage to get engaged. I’m kidding, RELAX. But really, engage. Ask questions to get to know each other and see if you actually like one another. If you catch yourself doing most of the talking, I want to congratulate you for having enough self-awareness to realize you’re a Chatty Cathy (I really do mean this). Self-awareness is something you’ve probably heard me talk about on the blog and how I believe it should be on everyone’s list of core-values. Self-awareness harnesses your ability to consciously halt certain behaviors that negatively affect you and those close to you.

Here are some questions that will get you both in a good flow of conversation. Asking genuine questions will make her feel seen, heard and appreciated (yes please).

  • What Was The Last Book You Really Got Into?
  • Among Your Friends, What Are You Best Known For?
  • How Many Siblings Do You have? - What Are They Like? or What Was It Like Being An Only Child?
  • What Would Be Your Dream Job?
  • What’s The Silliest Fear You Have?
  • What’s Your Favorite Movie & Why?

Don’t Talk About Your Ex

The only time your ex should be brought up in conversation is NEVER. Kidding, sometimes the exes come up if people are having deep conversations which I can appreciate but there is no reason to stay in the past. Look across, you’re with someone new. Don’t waste each other’s time. Be fully present, it will allow you to give this an honest shot. Generally speaking, talking about your ex, especially if you’re talking about how shitty of a partner they were — is VERY UNATTRACTIVE and says more about you than what you’re saying about them. Leave the past where it belongs, in the past.

Don’t Act Like You Don’t Care

Multiple women mentioned they’ve gone on first dates where the guy has acted extremely indifferent about being on the date. In my opinion, this is either a way of suppressing this guy’s nervousness so they project the opposite (not caring), or it means that the guy actually doesn’t care and is uninterested. In which case, why TF is he on this date in the first place?! They’re silly (I really want to use another word but I’m trying to tone down the sass) for wasting each other’s time and energy.

SO! Bring some energy— genuine interest into conversations, laugh and smile! If that means having to take a siesta before the date to fully be present, please do so. But most importantly, don’t go on a date you don’t care about. That’s just stupid, isn’t it?

If it’s a nervousness issue… RELAX. Go into the date as if you were rekindling an old friendship. Here is the most important thing… tie ZERO expectations to the outcome. A lot of people view things in black in white, good and bad, success and failure. This could really fck things up for you. I cannot stress enough that if you view dates in a “success / failure” outcome, you will be extremely susceptible to disappointment and anxious thoughts. Try to shift your perspective into thinking that you just had a great or not so great experience with someone. If it’s the latter, thats ok. They are not your person and you’ve just weeded out the wrong partner and are now closer to finding the right one ;). There are 7 billion people in this world, you’re going to hit it off with someone, this I promise you.

Don’t Try to Sleep With Her

Various women responded to my question by asking me to tell you boys to not even try to hit a home run on the first night. I understand that some ladies love playing baseball and have been on loads of teams, but generally speaking… if you try to sleep with a lady on the first night, it shows your true intentions and sort of ruins the way we felt about you. Some women need to establish an intellectual/emotional bond before they can deeply connect on a physical level. The only way to create an emotional/intellectual bond is if she feels seen, heard and appreciated through genuine interest and consistency.

If you only have one motive such as looking for some capital-F-fun, vocalize that. We actually really appreciate honesty (no, this isn’t a trap), and will find it attractive that you know what you want and the fact that you have enough self-awareness to realize you’re only looking for some capital-F-fun at the moment. Being honest from the beginning is so respectable and easy to do since there are no strong feelings yet involved. If you can’t be honest, work on your transparency/communication skills and save everyone time, energy and feelers.

Other Tips For A First Date

  • As a gentlemen, walk on the side of her that is closest to the street
    This is the simplest yet most thoughtful thing a man can do. It’s my personal favorite. Only two men have ever done this for me (every time) and it made me feel so protected by them. Hello, primal needs. Guys, we are no longer talking about surface-level attraction, we are talking about biological wiring, and that shit wins, every time.
  • Stay off your phone
    Unless it’s an emergency or something urgent.
  • Try not to get too intoxicated
    I get you might want to calm your nerves or enhance the experience, but going overboard could really fck things up for you.
  • Be on time
  • If she’s cold, offer her your jacket
  • Start taking it off before she even accepts or denies your offer. ACTIONS > WORDS.
  • Open doors for her
  • Text her that you had a nice time with her at the end of your date
    Only do this if you actually had a good time, lol. If you didn’t and don’t plan on seeing her again… you can wait until she reaches out and politely tell her you are not interested.
  • Do not, I repeat DO NOT go to the movies on the first date
    Dinner and a movie? How cliché. How about dinner and a stroll? Dinner and an activity where you can actually chat and get to know one another? Capeesh?

Ok! I’m done doing God’s work here. Until next time ;)

Stephanie Daily

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