Dating has never been easy and over the course of human history women have been told how to behave on a date, how not to behave on a date, and what to do to catch a man.
Times have changed.
No longer are we in a world where communication is limited and women are expected to stay at home, clean the house, and raise the children while their husbands earn the pay. No longer do we need to rely on “tricks” in order to catch a man to make us happy.
No, we date because we want to find love.
However, no matter how much times change, there is always dating etiquette to be followed in the search for Mr. Right, and it’s important that women know how to date successfully.
To be clear, successfully does not mean “catching a millionaire” or tricking your date into following you around like a lovesick puppy. Successful dating means being a lady, being yourself, being safe, and keeping the date going smoothly. This book is meant to guide you through that very first date, whether it’s with a man you’ll continue to see or a man you have no desire to ever see again. It’s not a “how to catch a man” book and it’s not your mother’s advice, it is real advice for the modern woman in the dating world, expertly given through real experience.
For those on the path to true love, you first have to make it through that first date.
#1 Getting The First Date
The dating game has changed immensely over the past few decades, and we’ve entered a new era of computer matches, equality of the sexes and a mixture of traditions blended between the old and the new. Previously, we were taught how to catch a man with our charm (and a few little “games” as well). Now, things have changed and we no longer look to our mothers for advice, seeking out advice from our peers out in the real dating world.
Because of all the changes, many women are confused about the most important aspects of dating, and even more confused about that sometimes ever elusive “first date.” Don’t worry: I’m here to brush away the old ways of thinking, debunk those outdated dating myths, talk about how people meet, and give you the real advice you need in order to get a date, get through that first date, and move on to date number two.
Online Dating
One of the biggest struggles in the dating world today is online dating. Although we hear fabulous statistics such as the famous Match.com’s “1 in every 5 relationships start online,” we also hear that online dating is dangerous and we’re likely to be murdered by someone we meet online.
So should we trust that we’ll find Mr. Right online, or should we assume all online men are axe murderers?
Actually, you shouldn’t trust either. There is no guarantee that you will find the man of your dreams online any more than there’s a guarantee you’ll meet another Ted Bundy online. One thing is certain however: Online dating isn’t nearly as “new” as people make it out to be.
Before the internet, people still submitted newspaper ads for dates.
“According to an article by Dr. Frederic Neuman at Psychology Today, even the Old West had newspaper ads for dates and marriages.”
The internet is simply a faster and broader way of newspaper dating.
So what does that mean for meeting online? It means you have just as much of a chance of meeting Mr. Right on a website as you do at a bar. The likelihood of meeting a liar or an axe murderer is also the same.
Our parents might warn us not to try online dating, however, because there are so many people in the world today. However, because women and men are both in the workforce working innumerable hours, online dating is much more acceptable than it used to be (and often much easier than trying to meet someone “by chance”). The only thing you need to remember is that if you’re going to try online dating, you will need to use the same kind of precautions as you would if you met a guy at a bar.
Friends Of Friends And Dating Your Friend’s Ex
Another big question asked by potential daters is if it’s okay to date your friend’s ex. Before you head off on that first date with the guy your friend is no longer with, you should go through a mental checklist:
- How long have they been apart?
- Does she still miss him?
- Is she with someone else?
- Have you talked to her about dating this guy?
- Is he interested in you or just trying to get back at her?
The truth is, no matter what rules you’ve heard or what advice you’ve been given, dating a friend’s ex will be tricky (especially if they had sex). It’s important to remember that sex creates an intimacy between two people and that there’s a certain bond between lovers that lasts long after they’ve stopped sleeping together. Because of that intimacy, your best friend could still harbor some unresolved feelings for her ex.
Go through the mental checklist before you date your friend’s ex, and speak to both of them openly and honestly before heading out on that first date. There’s nothing saying you cannot date him, but you do have to consider any negative repercussions.
Should You Wait Or Ask Him Out
If, on the other hand, neither of these situations applies to you and you’ve just happened to meet a nice guy at work, at the grocery store, or out on the town, how do you proceed from there? Should you wait and hope he’s interested enough to ask you out, or do you put your own fears aside and go for it?
Any dating rule book or motherly advice given is going to tell you to wait for him to ask you out because “a lady never makes the first move.” Once again, this advice is horribly outdated.
“It really is okay for a woman to ask a man out on a date!”
What Do Guys Think?
According to John DeVore at the Frisky, the gender roles are very blurred right now and men really do think it’s perfectly okay for a woman to ask them out. In all honestly, that is the best dating advice you will ever be given.
Just about a generation ago, women had stricter social rules to follow, but it’s important to remember that men did, too. It was not okay for a man to cry or show his feelings, it was not okay for two guys to hang out shopping at the mall, and men did not wear skinny jeans and hug each other.
Women were told to act like ladies. Women did not call a boy first, they didn’t stay out past eleven o’clock, they didn’t go to bars alone and they certainly didn’t ask a guy out for dinner.
It really is a new world. Still, even in this new blending of gender traditions, there are tactful ways of doing things (which I will discuss later) that ensure you are still keeping ahold of some of the more important gender roles – the ones that are not outdated.
How To Ask Him
When it comes to actually asking a guy out on a first date, how do you do it? There are a number of ways to ask a guy out, but you should consider what kind of guy he is first.
According to Dr. Jeremy Nicholson at Psychology Today, there are a few different methods of asking a guy out first. Although his article doesn’t cover every aspect of asking a guy out first, it is a good starting point. In the end, it all depends on the situation and what kind of guy you’re trying to get.
If you’re going to ask a shy guy out, it’s best if you take a “double date” approach. Its’ quite possible a shy guy will be intimidated by too much forwardness. Instead of dressing in heels and asking him to have drinks with you tonight in your best sultry voice, a shy guy needs a different approach. Be cool, be casual, look casual but cute (cute is always equated to approachable and harmless), and suggest a movie with a group of friends, but ask him when you have him alone. It’s important to let him know you’re interested in him by saying something like, “I’d really like it if you could be there.” That way he doesn’t think you’re friend zoning him.
A “man’s man” will need a different approach. Usually manly men are asked out, flirted with, and otherwise tempted on a daily basis by gorgeous women. You have two different options here. First, you can appeal to his humorous side and make witty jokes whenever you see him, then in the midst of mutual laughter confidently (confidence is key here) invite him out for a drink tonight.
Another approach is to just lay it out on the table with something along the lines of, “Would you like to have coffee with me tomorrow?”
Notice I said tomorrow? Tonight is too soon (he may have plans) and if he’s busy tomorrow, and interested in you, he will suggest another day of the week. It’s a little (but definitely acceptable) word play to save yourself some embarrassment if he’s not interested. If he says he’s busy tomorrow and does not suggest another day, he’s just not interested.
“Asking a guy out does not have to be complicated, and unlike bad advice you may have been given before, you don’t have to play any mind games.”
Be natural, be yourself, but be aware of what kind of guy he is, too.
#2 Where To Go And Who Pays
The next big first date question, after you’ve established that you’re going on a date, is where to go and who pays?
Traditionally speaking, the man has always been the one to fork over his credit card and take care of the bill. In today’s society, however, it’s not nearly that simple.
There are three rules of thought to paying the bill:
- He pays
- The one who asks pays
- You alternate
Any woman and man of previous generations will tell you that a guy should always pay for the date. In fact, even John DeVore at the Frisky says that paying is “what dudes do.” I tend to agree.
But let’s look at this in a broader perspective. Why should a man pay for dinner? In all honesty, no matter what gender traditions have switched in today’s society, a man is still a man and it is not only for his ego, but also his sense of obligation as a man, that he will choose to pay for dinner. Let him be the man.
Of course, modern dating sometimes suggests that the one who asks is the one who pays. In other words, if you ask a guy out to a baseball game, then you’re obligated to buy the tickets for you both. This is perfectly acceptable because asking him to a game (or movie, or any other event) usually implies to him that you have already purchased said tickets and need a partner.
However, if you ask a guy to dinner and he doesn’t pick up the bill, then it’s a matter of personal taste. Some women find that a man should automatically pick up the tab for your date even if you’re the one who asked. It’s the “gentlemanly” thing to do. Other women feel that it’s okay to pay if you asked him, but he should pay if he asked you on the first date. That’s an acceptable way of looking at it, too.
“Just don’t end up being with the kind of man who expects you to pay for everything because ‘it’s a modern world and he’s not obligated to fork out any funds on dating.’ This mentality is really just a guy using feminism and equality as an excuse to take advantage of you; don’t fall for it!”
Another option for paying is to alternate who pays. For instance, he gets the first one and you get the second one. This is a viable option for people who truly believe relationships should be equal and that it’s okay for the man or woman to pay. This is also a very good excuse for him to pick up the tab and ask you out on a second date (in which case, you would be the one paying next time).
Who pays is dependent upon the individual, but one thing is a definite in the dating world: You can always offer to pay by simply pointing at the check and then making eye contact with him when the bill comes and saying “how should we…?” (he will know you’re asking how to split the bill). In fact, many guys look at that in a positive light because you’re offering, which is a sign of equality.
Most of the time a guy will still pick up the tab and when he does, DO NOT ARGUE! Let him pay, thank him and smile, and leave it alone. If he says he’s got the bill, then he obviously is a firm believer that a man should pay. Don’t bruise his ego. A woman who’s being too pushy to pay can be a real turn off and might lose you the chance for a second date.
When it comes time for that big first date, there are plenty of places to go and each has their pros and cons. While you can opt for someplace like the zoo or an amusement park, here are a few tried and true first date hot spots that allow you the chance to leave early if you suddenly decide your prince is really just a frog.
Coffee Shops
Coffee shops make great first date places. For one thing, there’s no pressure to get dressed up to go to a coffee shop. You are free to wear your jeans and a comfortable top and be yourself. Also, coffee shops give you and your date a real chance to chat and get to know each other in a public, yet comfortable, setting. Another bonus is that you can have a coffee shop date any time of the day or night and still make it a good date, or you can leave in a hurry if he’s not what you thought he’d be.
On the downside, coffee shops have a lot of traffic, so there’s a decent chance you’ll run into someone you know (which can turn into a lot of awkward questions or embarrassing stories). Also, you’ll be really hyped up on caffeine which means you may not have the ability to form a coherent sentence.
Movies
Movies are a popular first date choice, and one that will probably stand the test of time. On the plus side, you can sit with your date in quiet company and then have something to talk about at the end (the movie). If you’re seeing a scary movie, you can jump and cower in the hopes your hot guy will put his arm around you, or you can gently brush his fingers in the popcorn bowl. You also get to tell what his taste in movies is, so that gives you more insight into his personality. Chances are, without much talking, you won’t feel the need to leave early.
On the downside, you won’t be doing a lot of talking, which means you and your guy aren’t really getting to know each other. Also, popcorn is not attractive when it’s stuck in your teeth.
Dinner
Dinner for the first date is almost always the favorite choice. An agreed upon restaurant means you know how to dress, you have the comfort of being in a public place, but still have the seclusion of a private table, and you can take a bite of your meal during those awkward silences.
On the downside, however, dinners are usually difficult to get out of. Unless you get a fake phone call, then you’re stuck until after dessert. Also, if there’s a chance you’re a messy eater, he will get to see you eat. Don’t order anything with noodles or messy sauce on the first date. Make sure you chew with your mouth closed, as well.
Drinking
Going out for a drink can be a good option for the seasoned first dater. A drink often helps people loosen up and relax. You also get the chance to gauge how much of a drinker this guy is. If he asks you out for a drink and then downs five beers in the course of two hours, there’s a good chance you want to skip the second date. Alcohol can help free some nervous inhibitions, but you can’t trust someone who relies on that much alcohol to relax on a first date.
Also, if you’re going out and having drinks on the first date make sure you don’t drink so much that you’re impaired to drive home. Keep yourself sober.
Places to Avoid
While these are some excellent first date choices, there are still some places to cross off your list. Do not go anywhere that triggers bad emotions (the park where you buried your dog, for instance) and avoid movies that make you cry.
Also, don’t do anything family oriented on a first date. You can wait until you’re actually in a relationship to introduce him to your mom. Besides, meeting someone’s family on a first date can be intimidating.
Finally, do not go anywhere that would be considered unsafe. Camping is not a good first date, and your house or his house are not good first dates. Anything that puts you in a position of discomfort is a bad idea, trust your gut.
#3 What To Wear
When it comes time for your first date, there are certain standards about how you should dress. Of course, some if these ideals might seem traditional and outdated, but they are still just as important now as they were fifty years ago.
Dress For Success
The first thing people notice about you is your appearance. If you’re wearing ripped up jeans and a decade old concert t-shirt to dinner, then you’re not dressed appropriately. Inappropriate dress is a sign of disrespect for both men and women, so it’s important to look your best for the place you’re going. That being said, it’s just as wrong to wear a cocktail dress and high heels to a baseball game. Be smart and look the part.
The Right Intention: Naughty/Nice
While you certainly don’t have to dress like a nun, you do need to dress in a way that conveys your real intent for the night. If you’re intention is to just relax and enjoy yourself, then it’s important to look relaxed. You cannot look relaxed in stilettos and a leather mini. However, if you have every intention of taking this man back to your place and you don’t mind either way if you see him again (which is also a valid reason for a first date), then that leather mini is probably what you want to wear.
Tried and true clothing advice for women, however, says that you should look like a lady. If you’re going to wear a skirt, make it just above or just below the knees. Do not show off your cleavage, and leave something to the imagination. Sensible shoes are an absolute must if you’re going to be walking around downtown. Summer dresses and sandals are great for warm weather, but don’t try to be sexy by wearing a low cut short summer dress in the middle of a snowstorm, your date will not think highly of your intelligence.
What Does He Think?
When it comes to clothing, men appreciate a confident woman. According to an article by Mark Amundsen at Match.com, it is best to enhance your best feature and to dress appropriately and confidently.
Men naturally respond to confident women, and beauty is certainly in the eye of the beholder. However, confidence cannot be faked.
“A confident woman radiates within herself, which only highlights and enhances her outer beauty as well.”
Whether you’re in jeans and a sweater or a flowing sundress, your best asset and most important accessory is going to be your personality.
#4 Keeping His Interest
One of the most worrisome aspects of that first date is whether or not you’ll have a second date. Dating can be hard work. It is thrilling, exciting, nerve-wrecking, and all kinds of chaotic feelings rolled into one. That’s what makes it so wonderful!
However, if you’re really interested in the guy you’re going on your date with, then it’s important to keep him interested in you, too.
There are plenty of places and people that will tell you that all guys look for the same thing in a woman. In general, this is true (personality, attraction, etc.), but on a deeper level it’s very, very wrong.
“If all men wanted the same thing, then all women would be exactly the same.”
Different men, like different women, want different things. Because of that the best, and most important thing, you can do on your date is to just be yourself. If you love fly fishing but can’t fathom the thought of flying to Paris for the weekend, then don’t pretend to be someone who adores Paris. Instead, be the girl who adores fly fishing and look for the guy who does, too!
Too many people assume they have to change who they are, or even worse, lie about their interests, in order to catchy the eye of the opposite sex. What happens on date two or three or four when he says he wants to take you on a plane to Rome for the weekend and you’re terrified of flying and hate to travel?
You have to be who you are first and foremost. Also, don’t play any mind games with him. I have read numerous books advising women to “play the game” and act a certain way (usually heinously) in order to get and keep a guy. Let me debunk that right now.
“No man wants a woman who lies or tries to play games in order to “snag” him. That kind of woman is not relationship worthy.”
If you have to pretend to be someone you’re not, or you have to trick him or play games with him to keep his attention, then he’s not worth it and you’re doing yourself a serious injustice.
On the other hand, there are definite things that you should talk about that will keep him interested and have his attention.
Things To Talk About
If you ask men what to talk about on a first date, and then ask women what to talk about, the answers are likely to be different. Men will advise you to talk about light subjects, focus on your career and your hobbies, or talk about your friends and family.
Women are usually advised to “be themselves” and yet be “fascinating and mysterious,” to talk about their ideas and dreams and even their feelings.
The truth is: First date conversations usually run a natural course. You’ll find that no matter where you go, there are usually a number of topics you and your date can talk about endlessly on. Still, if you need some advice, here are a few good places to start:
- Ask him about his job
- Talk about your favorite food
- Ask him what music and movies he likes
- Ask him if he has siblings
- Talk about something interesting in the news (like a scientific discovery)
- Ask about his hobbies
No matter what conversations take place, if he’s worth dating he will ask you questions in return to try and get to know you as well. If he doesn’t ask you question and just sits there answering yours like it’s an interview, then either jump in and tell him about yourself anyway, or find a man who will ask about you.
“A man who is genuinely interested in you asks you questions about yourself and wants to know your opinion.”
In other words, if the conversation isn’t going both ways, then the date is a bust.
Conversations To Avoid
It can generally be said that both men and woman agree on what not to talk about on a first date. While most subjects are at least somewhat open, there are a few taboo subjects you and your date should avoid:
- Sex
- Politics
- Religion
- Troubled past
- Crazy families
- Exes
- Addictions, bad habits, and money
There are sometimes, of course, subjects that arise unintentionally and you end up having a conversation about your past and comforting each other as humans who have shared some life experience.
While a lot of people frown upon this, the truth is it can be very relieving to be on a date with someone who has a past similar to (or at least just as troubled as) yours.
“People want to be in a relationship with someone they can relate to, not just a pretty face.”
If your date mentions he went through a bad divorce and doesn’t date often, it’s okay to say that you also had a bad divorce and you understand his feelings. If he mentions he’s a recovering alcoholic when you get ready to order your drinks, then go ahead and tell him about your brother or uncle who was also an alcoholic. A feeling of empathy and understanding often makes a conversation less awkward and a date easier. Plus, it gives you a little more insight about the guy you’re with.
If the conversation becomes awkward, it’s okay to change it and move onto something else.
Red Flags And When You Should Run
Regardless of what you’re talking about, there are always red flags and you need to know when you should call it a night. Red flags aren’t always easy to see, so it’s important to trust your instinct. Most of the time, even if the conversation is awkward and you and your date are arguing religion and politics, your instincts know whether or not he’s a good guy.
Still, some of those instincts can be rusty, so here are a few red flag pointers:
- He mentions he killed someone (this actually happens more often than you might think)
- He says “when we get married”
- He says “If you were my girl, I wouldn’t let you dress/act/talk like that”
- He asks you if you’ve found religion (this is never a first date appropriate question, no matter what the topic is)
- He asks if he can stay the night at your place (No! A gentleman would never ask, even if you had intended on sleeping with him tonight)
Anything suggesting he has a violent or obsessive past, anything that suggests he’s going to sponge off you for the rest of his life, or anything that suggests he could be trying to convert you to his political or religious beliefs are definite red flags and you should run.
Keep in mind, however, that some things are just human. Most of us are “fixer-uppers” and we have to take the good with the bad (the past is the past), but you need to know when the past is too much for you to handle and when his past may still be a big part of his present.
#5 Sex, Text, And The Second Date
After your first date, politely thank him. You don’t have to kiss (although the old rule “never kiss on the first date” is outdated now, many of us still abide by it), but a hug is generally acceptable – especially if things went well.
However, the big question remains: What about sex?
Should You Sleep With Him Now?
First date sex is very complicated and it depends on numerous factors. According to Doctor Fredric Neuman, first date sex is usually more acceptable the older you get. This makes a lot of sense socially, actually.
Dating in your teens and twenties is much more emotionally charged than dating in your thirties and forties. Also, because younger generations are still greatly influenced by older generations, there is a certain stigma against women who sleep with a guy on a first date. In other words, he might think you’re easy.
As you get into your thirties and forties, however, sex is easier to separate from emotions and the stigma is usually lifted.
However, although Dr. Neuman makes some excellent points, there’s one thing you still need to take into consideration and that is, “How do you feel about it?”
There’s a chance he might not call you after you have sex, and then there’s a chance he might not call you after the date anyway, so really the choice should be based on how you feel about first date sex, how he seems to be responding to you, and whether or not you can handle it if he doesn’t call.
“Some people are not able to completely separate sex from emotions, which is perfectly okay! However, if that’s the case you should not sleep with him on the first date.”
Only sleep with him if you are one hundred percent sure you’re ready to. It’s okay to. However, never sleep with a guy if you’re even a little unsure, if he’s pressuring you, or if you’ve had too much to drink. Sex can wait.
Wait For Him To Call Or Call Him?
No matter what happens after your first date (be it a hug or sex-filled night), you’re probably going to be sitting by your phone for the next few days waiting for him to call you.
While there are technically no set “rules” for this situation, you should still give a man his time and his pride and allow him to pursue you. A lot of people say, “If he’s interested, he’ll call you.”
In today’s world, however, men don’t always know what to say, especially younger men. There’s a good chance he’s waiting by his phone, too, hoping you’ll call him. In order to set your mind at ease and stop sitting by the phone, if he hasn’t called you in three days you can call him or send him a text and ask if he would like to go have coffee with you tomorrow.
Coffee is a safe zone, there’s no alcohol involved, which means he’s not going to assume it’s a booty call and you’re not asking him to dinner at your place, which means you’re not assuming the two of you are in a relationship. If he says no, then move on to someone else. If he yes, or says no but makes another definite date with you (not, “Maybe another time?” because that’s still a no), then it’s a go for date two.
The Rules About Texting/Sexting: No Naked Pics!
In closing up the first date advice, it should be noted that before any first date you should not be sexting. Do not send him naked pics of yourself (you really don’t know this guy), don’t mention how hot he makes you (because then he really will only be interested in sleeping with you), and don’t respond to any sexts from him before the first date (he’s obviously not a quality guy).
Dating is challenging at best. Just be yourself, use caution, and enjoy your evening. He might be Mr. Right. He might not be Mr. Right, but you can always enjoy the moment for what it is.
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