Conquer & Win

First Date Tips: 2019 Mega Guide

Are you going on a first date soon, and want to make sure it goes well?

If you asked most people for first date tips, they’d probably tell you the same thing: “Be yourself.”

But if you’ve been on a few first dates with women before, then you probably know “being yourself” doesn’t always work.
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In fact, I’m sure you remember certain times you messed up a date. You might have said something stupid or did something that turned her off. All by “being yourself.”

So how do you really make sure your first date goes well -- enough to make her look forward to a second date with you, then a third, then a fourth, and so on?

This article is the last article you’ll ever need. So pay close attention, take notes, and get ready to start making women like you on the first date.

Use the table of contents below to skip to the sections you want to read.

So first things first. Let’s start with:

Area #1: The Plan

Nod your head if the following story sounds familiar to you…

You asked a woman you just met to hang out with you, and she said “yes.” You were ecstatic -- and you were determined to make sure the date would go well.

So you went ahead and:

  • Bought a whole new outfit for this date -- new Nikes, new jeans, new jacket, new everything.
  • Got a haircut and made sure you were clean-shaven.
  • Brought flowers for her.
  • Treated her to a fancy dinner.
  • Acted like the perfect gentleman throughout the date.

You thought the first date went well. You thought there was definitely some chemistry.

She seemed interested, smiling and flirting the whole time. She laughed at your jokes and you two expressed similar interests.

After the date ended, you hinted about going on a second date, and she seemed to like the idea. You went home feeling like you were in love.

You were smitten. You couldn’t stop thinking about her.

After the date you texted her to tell her you had a good time, and you suggested maybe doing it again sometime soon.

So a few days later, you texted her to see if she’d like to meet up again tonight.

No answer.

You texted again, asking if she got your message. Still no answer. In fact, you don’t hear a peep from her all day.

That night, you went to bed and wondered what happened.

Maybe she just got busy? Maybe her mom got into a car accident or something? Maybe she was hopping into the shower right as she saw your message and she dropped her phone in the toilet?

Whatever it was, you never found out. You never heard from her ever again.

Did something like this ever happen to you?

If so, then I have some good news and bad news for you…

The good news is that it doesn’t mean you’re a loser. Even the smoothest, most successful men out there go on first dates that never lead to a second one.

In fact, most first dates never lead to second ones. So if yours didn’t, it’s probably not your fault.

What’s the bad news?

The bad news is that if you “don’t know what went wrong,” then you’ll probably keep having first dates that never lead to second ones.

Meaning, you may be making some mistakes -- or believing the wrong things about dating -- that’s sabotaging your chances at getting second dates with women.

So let’s fix all of that in this article. And it all starts with one thing: Planning.

Right now, let’s get the bad stuff out of the way...

The Wrong Ways to Plan a First Date

There are basically two ways to plan a first date wrongly. They are:

  • Not having a plan at all, and
  • Not knowing the wrong kinds of dates, and ending up planning them.

Let’s take a look at each one in turn.

Mistake #1: Not Having a Plan

Some people think that the best first dates are the ones that are “unplanned,” where you meet somewhere, “just hang out,” and let things unfold as they will.
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Unfortunately, as the wise old saying goes, “Failing to plan is planning to fail.” And that’s definitely true for first dates.

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Because if you want your first date to lead to a second one, then your first date must leave a good impression on her -- enough to make her think, “Wow, I want to do this again.”

But when you don’t have a plan, then you’re leaving everything up to chance. And as you already know, most first dates don’t lead to second ones.

So if you leave things to chance, your odds won’t be very good.

Make no mistake -- you need to plan.

And speaking of planning, here’s the second mistake:

Mistake #2: Not Knowing the Wrong Kinds of Dates, and Ending Up Planning Them

Some people would advise you to treat a woman to a fancy dinner on the first date.

Others might suggest watching a movie with her.

Still others would suggest you take her to a bar or club instead.

Unfortunately, these are all actually bad first date ideas for the following reasons:

  • A fancy dinner is expensive.
  • Watching a movie means you’ll be sitting for two hours doing nothing.
  • And bars and clubs serve alcohol, which can get you drunk.

To be clear -- when it comes to first dates, anything expensive, or involves you doing nothing, or can get you drunk is a bad idea.

  • If the first date is expensive, she’ll either feel you’re a little too invested in her too soon, or she’ll feel like you’re “bribing” her… or both.
  • If the first date involves you doing nothing, there’s a high chance she’ll get bored… and that means she won’t want a second date.
  • If the first date involves alcohol, her defenses will be up -- she’s heard all the “Pill Cosby” stories and will be on her guard.

See what I mean?

Now that we’ve established how not to plan for a first date, let’s take a look at the “beBecause if you want your first dst practices” side of the coin.

The Right Ways to Plan a First Date

And that should give you a good enough idea of what a good first date would be like. A good first date would be inexpensive, involves an activity, and doesn’t involve alcohol.

With those elements, you stand a pretty good chance of leaving a good impression on your date, making her want to see you again sometime.

Here are some activities that have most, or all, of the elements of a good first date.

12 Good First Date Ideas

You might be worried that if you don’t spend a lot of money on your crush you’re never going to get past the first date. Don’t worry too much.
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There’s a reason why girls go for aspiring musicians and starving artists. Even though they don’t have any money, women can smell their passion, and that’s so much more important than the numbers on your bank statement.

Focus on being passionate and fun, and the rest will fall into place (and she might just fall into your lap).

According to a survey performed by a popular wealth management service called Personal Capital, 78% of Millennials say that “finding love” ranks higher on their list of priorities than “making money.”

What does that mean?

Women aren’t all gold-diggers looking to use you for an expensive dinner. Use the first date to get to know her, not blow this month’s salary trying to impress her.

With that said, what are some cheap first date ideas?

  • A hike. This is my personal favorite. First dates can be nerve-wracking, and it can be even more nerve-wracking if you have to sit directly across from her like you’re on a job interview. You don’t want to feel like you’re taking mental notes of all her beautiful features while wondering why someone like her would ever go out with someone like you.
  • Take your dog (or dogs) to the park. A social media analyzer recently looked at the top 1000 Tinder profiles in the world and found that one of the most popular pictures among the best-converting Tinder users is a picture of you with your dog on a sunny day. If you have a cute puppy, be sure to show him off.
  • Visit a flea market. Browsing through various items can tell you a lot about a person, and antique shopping tends to come along with a lot of fantastic conversation starters. It’s like that scene from Good Will Hunting: You can each pick out and joke about certain items. It offers a lot of opportunities for good-spirited fun.
  • Attend a free concert or local festival. Keep your eyes peeled for cheap local events in your community and you’ll never run out of ideas for a fun, interesting, and cheap first date. But notice the common thread among all these ideas: each of these activities has you doing something.
  • Visit an art museum. There’s always something interesting and exciting to see at art museums. If you think that they’re stuffy, academic, and boring, you’d be surprised at how accessible and entertaining modern art has become. Check one out with the girl you’re interested in.
  • Go see a local play. This one could be totally hit-or-miss. I’ve personally seen some great local plays, along with some awful bombs. Either way, it’s entertaining and often costs less than a couple drinks at the bar. Try to see a shorter play (or collection of plays) that run 30 minutes at a time so that you can dip if it’s boring.
  • Ride bikes. This one’s active and fun. If you’re even more adventurous, you could find a bike rave and invite her along.
  • Visit a playground. There are playgrounds all over the place, so this one’s pretty easy. Just make sure that class isn’t in session when you’re taking turns swinging on the monkey bars.
  • Go to a comedy open mic. Just like the local play, this one can be hit-or-miss. If the comedian’s one of those guys who likes to pick people out of the audience to make fun of, get out of there ASAP. Those type of comedy routines are actually pretty popular, and you don’t want to deeply offend her on the first date.
  • Mini Golf. Mini Golf is amazing, and if she doesn’t know how to play, that opens up some awesome opportunities for playful, flirtatious touching.
  • Pokemon Go. Remember that first week of Pokemon Go? Where the whole world was brought together by our common interest in “catching them all”? This is something you can bring up during a hike. As long as she likes Pokemon, that is.
  • Volunteer. A great way to show her that you’re caring and fun is to take her on a “volunteering” date. Maybe something where you hand out and/or prepare meals for the needy.

Hmm. Lots of good ideas up there. How do you pick just one for the first date?

That’s going to depend on what she likes, right?

For instance, if during your conversation with her she tells you she likes volunteering, and it turns out you volunteer for a soup kitchen on the weekends, tell her: “Wow, interesting. I serve at the local soup kitchen. Is your weekend free? I’ll show you around.”

Or if you learned you’re both artistic people, you can tell her: “Have you seen the new displays at the museum? No? We should totally go. How’s your schedule this week?”

See how it goes?

But you can’t do that if you don’t know a bad first date idea from a good one. You now know, so you can now plan dates correctly from the get-go.

Those are our first date tips for planning and you can find our first date questions here. Now let’s move on to the next area to master.

Area #2: The First Impression

Almost nothing is more important than a first impression.

Social psychologist Dr. Heidi Grant Halvorson calls this “the primacy effect,” and it’s very, very important when it comes to dating -- and life. The first impression is the lens through which everything else about you is perceived.
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For instance, consider a math test given to two students, Timmy and John. For our (slightly modified) example, assume they’re both taking a twenty-question test. In the first half, Timmy scores eight out of 10, and John only scores four out of 10.

If you were grading their tests, at this point you would think to yourself, “Timmy is smart -- much smarter than John,” (or at least a better math student).

But then, after the next period, when they take the second half of the test, Timmy only scores one out of ten, while John scores a fairly-impressive nine out of ten. The final scores, then, are nine out of 20 for Timmy and 13 out of 20 for John.

If people were perfectly logical, they would conclude (rightfully) that Timmy is the worse student, that their first impressions weren’t accurate.

But that’s not what happens. Not at all.

Instead, because Timmy made a better first impression, he’s given more leeway. Your brain has already made up your mind about Timmy’s math ability: He’s the smarter student.

It’s not fair, but it’s also the reason why tall, attractive, and masculine men get more leeway with women. If you walked into the bar (or restaurant or class or wherever) looking like a guy she wants to date instead of just another average Joe, she’s going to forgive your awkward jokes and social tics.

So, put simply: If you want to raise your chances of making her like you, then put some effort into making a good first impression.

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So, put simply: If you want to raise your chances of making her like you, then put some effort into making a good first impression.

Here are a few good ways to do just that:

  • Look good. Dress in clothes that fit you well and show your personality.
  • Groom well. Maintain a good haircut, brush your teeth, shower, cut your nails, trim your beard if you have one.
  • Don’t be late to the date, but don’t be too early either. Just show you have enough discipline to show up on time.
  • Don’t bring flowers. You’re not courting her, are you? (And even if you are, I repeat -- don’t bring flowers.)
  • Don’t pick her up. Instead, meet somewhere close to your place and with lots of different activities to do, including the activity you suggested in the first place.

Apart from these first date tips, there’s not much else you can do to increase your chances of making a good first impression. But they’re more than enough.

Now let’s move on to the third area you’ll need to master: Actually giving her a good time.

Area #3: The Date Itself

If you’re anything like me, you’ve gone on some first dates that have been real duds.

Sometimes that’s natural; you two just didn’t click like you thought you would.

But other times, it has nothing to do with the person and everything to do with the date itself.

Here are some first date tips that could help:

Touch Her

Touching her is important for many reasons:

  • Physical contact helps build attraction.
  • It shows her you’re confident.
  • It establishes the frame; it lets her know “this is a date,” and that’s how you avoid the friend zone.

Pick an activity that has you both on your feet. Unlike sitting across from her at a diner, this gives you plenty of opportunities to touch her, which is one of the most important aspects of physical attraction. You can grab her hand while you’re walking in the park or put your hand on her waist as you stroll through a flea market.

But what if she doesn’t like being touched?

If she tenses up or moves away when you put your hand on her shoulder, that means one of two things:

  • Either she just isn’t that attracted to you...
  • ...or she’s shy and simply isn’t comfortable with being touched.

Either way, stop touching her. Respect her personal space. Later on, she might lighten up and let you touch her again.

Get Moving

Also, as I mentioned earlier, if this is a girl you’re really interested in, you might feel the “first date jitters.” That’s normal.
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Even better -- the jitters are easy to fix. Physical activity releases endorphins that act as natural painkillers, which get rid of the jitters fast.

That’s another reason to pick an activity that gets you moving.

According to the Anxiety and Depression Association of America, studies show that physical activity is a great way to reduce stress, and first-date jitters are nothing more than acute, temporary stress. That means that, by making sure you’re both on your feet, you hit three birds with one stone:

  • She won’t notice your shaky hands if you’re both moving around a lot.
  • Through associative learning, she’s going to start attributing the endorphin release to spending time with you, which might help make an otherwise boring date more interesting and fun.
  • If the date is boring anyway and you find out that maybe she isn’t as interesting or funny as you thought at first, at least you both got outside for a little bit. As the ADAA shows, that’s great for your mental health.

Carry a Good Conversation

Picture this: You showed up early to your economics lecture. While waiting for the class to start, a pretty brunette girl walks in, briefly locks eyes with you, then -- lo and behold -- sits down right next to you.

How would you react?

If you’re like most guys, you’d probably freeze.

Even though you received a clear indicator of interest -- even though your whole body is screaming at you to talk to this girl -- you pull out your phone and pretend you suddenly received an important text, and then you start scrolling through Instagram instead.

You don’t want that same feeling on your first date. After asking about her day, you don’t want to sit there, letting the anxious silence build, giving her time to wonder why she ever agreed to go out with you in the first place.

You must know how to carry a good conversation.

What NOT to Talk About During the First Date

But first, let’s start with the obvious: Avoid sensitive topics like politics and religion. The first date is not the time to ask about what she thinks about a top marginal tax rate, or America’s participation in the United Nations. You want to be fun and engaging, not boring and dry.

Politics and religion -- now more than ever -- are extremely polarizing topics. If she’s a democratic socialist and you’re a die-hard libertarian, instead of having a fun day walking through the park and then taking her to get an ice cream cone, you’re going to waste your time arguing.
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You also want to avoid broad, interview-like questions or conversation starters, such as, “Tell me about yourself.”

Take a second to consider what you say when someone asks you something like that: Do you dive in to your dying passion for bass guitar? Your favorite movies? Your life goals and aspirations?

No, you don’t. Instead, you’re unable to wrap your mind around such a broad question, so you stumble and say, “Oh, you know… I’m just a normal guy, really.”

Oh, and here’s a friendly tip: Don’t talk about your exes on the first date.

Seriously. Just don’t. It’s way too soon.

If you don’t want to weird her out, wait until the second date before you talk about your love life. (Unless, of course, she brings up the topic of exes first -- then it’s okay. It’s a sign she likes you like that.)

And that leads us to the obvious question…

So What Should You Talk About?

If you want to be the man in the relationship (and, by extension, make yourself as attractive as possible), you need to lead, in words and in action.

Not only should you decide where to go and what to do, but you should also decide what to talk about.

It’s not that hard. You can start the date by greeting her with a handshake or high-five (the touch is important), and then tell her:

Okay, so first we’ll go to that smoothie place I told you about. We’ll get a couple smoothies, and while waiting, we’ll get to know each other better. Then I’ll take you to the Sky Tower where I’ll show you the night view I was talking about.

“Okay, so first we’ll go to that smoothie place I told you about. We’ll get a couple smoothies, and while waiting, we’ll get to know each other better. Then I’ll take you to the Sky Tower where I’ll show you the night view I was talking about.”

Simple, right? And then when you’re at the smoothie bar, some good questions to “grease the wheel” include:

  • “So tell me about yourself. You said you were from (place), right?”
  • “You told me you were in media. What, behind the cameras or in front of them?”
  • “I like your fashion style. That choker really caught my eye. It’s not African, is it?”

Then, on your way to the Sky Tower, you can talk about anything that’s going on around you:

  • “Sure is cold this time of year, isn’t it? I like it, though. I’m not a tropical person.”
  • “I think you’ll love the Sky Tower. You’re not afraid of heights, are you?”
  • “It’s a 10-minute walk there, so let’s play a game to pass the time. I ask you one question -- any question, and you should answer it -- and then you ask me one question. Game?”

Really simple. As long as you don’t mention any taboo topics, it doesn’t really matter what you talk about.

The important thing is to make her feel more and more comfortable with you. When she’s comfortable, everything else becomes much easier.

Now, let’s talk about one of the biggest first date killers of all…

The Awkward Silence and How to Beat It

Sometimes, you just run out of topics to talk about, and you run into an awkward silence with her.

That’ll kill the date fast unless you do this: ask an off-topic question that starts an entirely new conversation.

You can simply say something like, “This is totally off-topic, but…” and then ask her one of these five questions:

  • “Who’s your favorite Disney princess/villain?” Girls love Disney. Hell, everyone loves Disney. It’s almost ubiquitous. In the off-chance that they don’t, though, they’ll be sure to tell you why, sparking yet another conversation.
  • This question can tell you a lot about her: Which Disney princess does she identify with the most? Does she see herself as a hard-working and over-looked Cinderella? Or a tough-as-nails Mulan?
  • “If you had three wishes, what would they be?”
  • This is a fun and light question. Be sure to roast her if she wishes for more wishes.
  • “What did you want to be when you were a kid?”
  • This way you can learn about her dreams and aspirations, without asking something as professional as “Where do you see yourself in five years?” It can also lead you into a question like…
  • “So what made you want to be a X?” (where “X” is, of course, whatever her current occupation is).
  • People love talking about work. In Stephen King’s On Writing, he says that two topics never fail with any audience: money and sex -- and that’s probably because people spend most of their lives at work and, well, sex is sex.
  • Find out why she does what she does, and how it ties in to what she wanted to be when she was a kid.
  • “If you could be anything, what would it be?”
  • This is often different from what she wanted to be when she was a kid, since that’s often something silly, like a princess or the president.

Now, here’s a few extra tips for when you’re a naturally shy guy...

Dating Tips for Shy Guys

At this point in the article, you need a reminder that it’s important not to feel overwhelmed. It’s something that you can’t really control).

If you’re a naturally shy guy, the problem isn’t that you don’t know what to say, but that you think too much. You get stuck in your own head.

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You don’t need to be perfect -- just good enough. It’s okay for there to be pauses during a conversation; take the time to collect your thoughts, and allow yourself to not be perfect.

You don’t need to dominate the conversation. A lot of times it’s best to sit and listen, and that’s especially true when she’s speaking passionately, waving her hands and projecting her voice. No one likes to be cut off when they’re saying something they think is important.

There’s the “60/40 rule of conversation.” For best results, let her do around 60% of the talking -- and when she’s talking, really do listen to her.

Besides, there’s the “60/40 rule of conversation.” For best results, let her do around 60% of the talking -- and when she’s talking, really do listen to her.

But if there are awkward pauses, remind yourself of how you talk when you’re with your best friends, or when you’re talking to a family member about something that you’re passionate about. It’s not that you’re not an interesting person -- it’s that you do a poor job of expressing yourself because of inexperience.

The only way to get rid of inexperience is through experience.

Now, here are a few more tips to deal with your shyness:

  • Put your phone away. This trains you to focus on your conversation instead of “escaping” from it by checking your phone.
  • Don’t be self-deprecating. It’s okay to apologize if you said or did something wrong, but it’s not okay to apologize for no reason.
  • Be nice, but not too nice. You’ll want to joke around with her, tease her, and push the boundaries of “how far you can go” with her. If you don’t, it’s straight to the friend-zone with you.

And speaking of pushing the boundaries, we now move to the fourth and final area to master:

Area #4: Flirting

Yup -- we’re about to talk about first date flirting tips.

Now, some people say flirting has no place in the first date. They might say it should come in the second date, or fourth date, or seventh date, or even after three months of dating.

Sorry, I disagree. And so should you.

Because let’s face it -- that’s where you want things to go anyway, right? And any woman who agrees to go out with you one-on-one has the same thing on her mind -- trust me.

The thing is: She’ll only flirt with you if she likes you like that.

She won’t flirt with you if she sees you as “friend material.” But that’s exactly what she’ll see you as if you just talk and talk.

So let’s break the flirting part of the first date down.

What Should You Expect on the First Date?

Again, the endpoint of a date is a relationship, or sex, or both. Let’s just be real here. These are the best outcomes of any date or series of dates.

There are other possible outcomes, too. For instance, she might friend-zone you.

Or you might realize she’s not your type, and you friend-zone her.

Or you both might realize it’s not a good match, and the date ends early.

My point?
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Anything can happen on the first date. But if you focus too much on making her fall in love with you, it probably won’t happen.

If you talk about your exes, she’ll tense up. If you treat her to a fancy dinner, she’ll feel like you’re bribing her. If you bring her flowers, she’ll feel trapped.

You’ve noticed, right? If you talk about your exes, she’ll tense up. If you treat her to a fancy dinner, she’ll feel like you’re bribing her. If you bring her flowers, she’ll feel trapped.

So here’s what you should do instead -- have no expectations.

Nada. Zilch. No expectations whatsoever.

All you can do is be prepared for the possibility that you’ll actually like this girl.

And when you do, that’s when you focus on doing three things:

  • Avoid making any of the obvious mistakes.
  • Focus on giving her a good time.
  • And push the boundaries of how far you can go with her.

Now, let’s talk a bit about the third item on that list.

How to “Push the Boundaries”

Here’s the thing: Some women are actually okay with, say, kissing on the first date.

Others are even okay with sleeping together after the first date.

On the other hand, other women are more traditional. They’d rather wait a few dates before even giving you a peck on the cheek.

Now, there’s no way of knowing what a woman’s “boundaries” are for the first date, right?

And that’s why you should find out.

Now, you might be thinking: “Wouldn’t she get turned off if I’m too pushy?”

Sure. But that’s only if you push her boundaries the wrong way.

Here are the different ways to push the boundaries with her, and the right and wrong ways to do each.

Through Conversation

Normally, conversations start out over light, casual, harmless topics. You might get to know each other better, try to find common interests and beliefs, and maybe even tell a few funny stories.

Later on, you’ll want to get more serious. Remember, you both know where this date is going, and it’s not about becoming just friends. And so you’ll have to address the elephant in the room sometime, otherwise the conversation will get boring or awkward real fast.

This is easy to do by playing the “questions” game -- you ask her one question, then she asks you another question. All questions are allowed, and you both must answer the questions -- although each of you has one “pass” for when you get a question that’s too private, emotional, or inappropriate.

This is an opportunity to ask progressively more intimate questions, such as:

  • “When was the first time you fell in love?”
  • “What was the best thing your worst ex ever did to you?”
  • “When was your first kiss?”

Take note -- if she mentions “pass” to any intimate question, it means she doesn’t like you like that. But if she’s game, then keep the game going.

But don’t just stick to talking, though...

Through Touching

If you want your first date to lead to a second one -- or better yet, a relationship or romantic encounter that same night -- then you must touch her. It’s non-negotiable.

But you must touch her the right way. For instance, it’s not appropriate to nuzzle her neck when the date started five minutes ago.

So what’s appropriate?

Think of the following kinds of touches.

  • A handshake or high-five.
  • Letting her loop her arm around yours as you stride side-by-side.
  • Putting your hand on her shoulder or the small of her back.
  • Touching her hands (such as by reading her palms).
  • Putting your hand on her hip.
  • Touching her neck.
  • Massaging her shoulders.
  • Fondling each other.
  • Kissing.
  • Sex.

Notice how the kinds of touches go gradually from “harmless” to “risky”?

The key to pushing the boundaries through touch is by “climbing the ladder,” with your touches becoming riskier and riskier as she gets more and more comfortable with you.

If she’s okay with you putting your hand on her shoulder, later on try touching her hands by reading her palms. If she’s okay with that, then later on, put your hand on her hip or leg while you’re talking. And so on and so forth.

For instance, if she’s okay with you putting your hand on her shoulder, later on try touching her hands by reading her palms. If she’s okay with that, then later on, put your hand on her hip or leg while you’re talking. And so on and so forth.

Now, if at any point she shows some discomfort from your touch, dial back right away. For instance, if you put your hand on her leg and her eyes dart from your hand to your eyes, an uncertain look on her face, then you casually stop touching her there.

You act like nothing happened, and you continue building rapport throughout the date.

Later on, when you sense she’s more comfortable, try putting your hand on her leg again. If she doesn’t resist, then you can continue climbing the ladder.

Now, at some point, your date might give a clear indication that she doesn’t like to be touched beyond a certain point in the “ladder.” When that happens, that means you’ve established her limits. Now you can decide whether or not to pursue a second date with this lady.

But when she’s game, congratulations. You’re on the right track.

Through Moving Her

Lastly, it’s important to move her from one place to another during the date. It’s never a good idea to stay in one place for the whole date.

The idea is to start somewhere harmless (like an ice cream or smoothie joint), then move her somewhere else (like a flea market, fair, museum, etc.), and then move her somewhere close to your place (like a bar or coffee shop).

That way, when things turn out really well and you feel the chemistry between you, it’s easy to invite her to your place for a nightcap.

On the other hand, if early on you decide you’re not a good match for each other, you can cut the date short at any of the locations. The first date might not have led to a second date, but at least you went places and had some fun.

You’ll also need to know that when a woman hesitates to go with you anywhere, it means she’s not comfortable with you. In this case, you can stay in the location and see if her mood changes as your interaction moves along… but if it doesn’t, then take it as a sign that the date won’t go anywhere.


After reading this comprehensive article, you should be able to kill it on your first date. If you want an ultra-condensed, TL;DR version of the tips above because your date is soon, we’ve got you covered.

  • There are two wrong ways to plan a date. The first is not having a plan at all. The second is to not know the wrong kinds of dates, and end up planning them. The wrong kinds of dates include dinners, movies, and events with lots of alcohol.
  • Some cheap first date ideas include going on a hike, taking your dogs to the park, visiting a flea market, and more. Try to stay on your feet, it’s a good way to make sure you don’t let the first date jitters get to you.
  • First dates can often be boring, particularly if you choose something you don’t both enjoy. Sometimes people don’t vibe, so if it doesn’t work out, it doesn’t work out. It’s not always your fault. You can always get more dates.
  • The first impression is important. It’s maybe the most important aspect of dating, and even interacting with others. Put some thought into how you want to be perceived, and try your best to make sure she sees you that way, too.
  • We included five conversation starters in this article, but one that’s usually pretty good is this: “If you could be any Disney princess, which would you be and why?” Also, get her talking about her job. Everyone has a lot to say about their jobs.
  • Of course, avoid sensitive topics like politics and religion, even if those topics are important to you. Keep the first date fun and light.
  • And if you’re shy, the problem is you probably just think too much. Everything doesn’t need to be perfect.
  • When a woman goes on a one-on-one date with you, you can bet that the possibility of a getting in a relationship or having sex with you (or both) is at the back of her mind. So it’s best to pretend it’s not on your mind too. Build rapport with small talk and finding common interests, and then flirt your way forward.
  • Push the boundaries to find out where they are. Some women don’t kiss on the first date. Some do. Some are willing to do even more than just kiss on the first date. But you’ll never know unless you push the boundaries.

About the Author Eddy Baller

I'm the founder of Conquer & Win, and since 2011 I've been helping guys get into great relationships, build their core values as men, and become confident. I'm published on Lifehack, Order of Man, POF and many more. I want to help you get socially confident and live to your full potential. Feel free to contact me here.

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