Today’s question comes from an anonymous reader:

“I’m a normal Monday through Friday 9-5er who doesn’t have the most amount of time to date during the week. I’ve been filling my weekend calendar with flakey, half-interested girls (and let the vicious cycle repeat). What are ways to break that funk and find meaningful connections?”

Essentially what you’re asking are for some good dating strategies if you’re busy.

But before I answer that, there are a few parts to your question that I want to address.

WHY DO WOMEN KEEP FLAKING ON ME?

First, if you’re constantly planning dates with women that flake, it’s a sign that something is off with you, the women you’re asking out on dates, or both.

Here is the blunt truth: Busy people will make the time if they’re genuinely interested.

I live in NYC, one of the biggest dating markets with some of the busiest people.

I’ve known women who straight up go to work in their full blown date outfits, full face of makeup, so they can head straight to dinner after a brutally long day.

To butcher-quote the great Jeff Goldblum, “Girls that are really interested will, uh, uh, find a way.”

So let’s figure this out.

There are a few reasons a woman would flake on a date:

Reason 1: She’s genuinely busy or something came up (Least likely)

Life happens, and sometimes things will come up last minute, and she’ll have to cancel.

Reason 2: She was being polite when she said yes (Somewhat likely)

Same reason as above, except she wasn’t doing it to be mean. She was giving you a soft rejection by saying yes in the moment and cancelling later.

Reason 3: She sucks (Somewhat likely)

Sometimes people just suck and cancel. Most likely reason is that she wasn’t really into you, but said yes to a date cause she had nothing else going on.

How can you tell if something genuinely came up, or she sucks?

An easy way to tell if she’s genuine: she offers to reschedule, with specifics plans.

E.g. “Something came up tonight, can we reschedule and grab a drink next Sat, same time and place?”

What if she doesn’t offer to reschedule and says something like “Let me check my calendar and get back to you.”?

Take it as a “Nope, she’s not that into you.” Be polite and respond, “Sure, just let me know” Then let it be unless she contacts you again.

(And before you ask if you should reach back out if you don’t hear from her in a few days/weeks, you could. But in my experience, anyone that wants to hang out will make plans right then and there. Be honest, tell me you’ve never said: “Let me check my schedule” when you really want to say “Let me stall while I think up an excuse to say no.” I know I have.)

But wait, there’s one more!

Reason 4: Your approach to first dates is off (HIGHLY likely)

Any of the above can be true, but it all starts with this: The fact that you’re continually booking dates with women who flake tells me something’s off with your process.

You see, the key to breaking this funk isn’t about a specific a line to text her or pic you should have on your dating profile (those matter, but are secondary).

The key to a great first date where a woman won’t flake on you is all about rethinking what a first date is to begin with.

THE DUMB MISTAKES I USED TO MAKE WITH FIRST DATES

Protip: Never bring flowers on a first date

Let’s take a trip into the mind of Peter in his late teens and 20s.

To young Peter:

  • First dates are like first impressions They’re important! And like first impressions, you only get one shot. So it’s my only chance to show her how amazing I am!
  • First dates should be IMPRESSIVE Since this was my one shot, I need to go big. Elaborate, meticulously planned, day-long affairs. I’ll surprise her with hard to find tickets to her favorite band, then we’ll grab dinner at the new spot I read about in the NY Times. We’ll end the night at one of those annoyingly hard to get into speakeasies, where craft cocktails are $25.

Solid gameplan right?

How do you think I did?

Well, I went on a lot of first dates. Sure, I hooked up a few times. And sometimes got that 2nd date.

But anything beyond that was a bust. As I kept frustratingly going along with this strategy, a pattern started to emerge.

I was going on more and more bad dates with women who I just didn’t click with, and I was slowly going broke.

A 23-year old doing the occasional freelance job can only buy so many concert tickets, nice dinners, and $25 cocktails. (Of course I insisted on paying for everything.)

It wasn’t until a night of complaining did my friend Saba point something out.

“Why are you spending so much energy trying to impress these girls? You should be trying to figure out if you like them.” She said.

It was subtle but eye-opening.

I was so distracted trying to convince these women that I’m THE guy for them with over-the-top dates, I never stopped to consider if THEY were actually the right person for me.

It’s like I was trying to find a new ice cream flavor I’d like.

But instead of just going down to the local ice cream shop and sampling a few different flavors every now and then, I was overcomplicating things.

I was going out and buying an expensive ice cream maker, fancy ingredients, investing all day making it from scratch to see if I’d like it.

I was wasting so much time, money, and energy! And yes I blame all those damn Rom-Com movies for making me believe I needed to pull out some grand gestures to win over a girl. (Shout out to Hitch. I still love you.)

Regardless of the why, It had to change.

DESIGNING THE BETTER FIRST DATE

Redesigning the first date was simple: just do the opposite of everything I was doing before.

Instead of focusing on trying to make her like me, I’d focus on seeing if I’d like her First impressions are still important. But if all I focused on was getting her to like me, then I’m not allowing her to contribute to our date. It’s one-sided. It’s all about me. That’s not what relationships (friendships, casual, or long-term) are about.

Instead of going all-in with elaborate dates, keep it casual I love all out, impressive dates, but save them for someone you have a real mutual connection with. Stop “wasting” them on girls you don’t know. Think of those fun creative dates as a side of you only special girls get to see. For now, keep dates casual, low-risk, and inexpensive.

Here’s why these changes are great for you going forward:

  • It minimizes disappointment It’s easier to get over a bad coffee date that cost you $5 and an hour, versus one you pull out all the stops for, like an amazing show and drinks at your favorite cocktail bar.
  • It’s cheaper Self-explanatory.
  • You’ll get better at date conversation Elaborate dates are kind of like special effects in big budget summer movies. A lot of the times they’re used to distract from a shitty premise. Stripped down dates like coffee and a walk are like indie movies, it’s all about the dialogue and characters. And since these kinds of first dates are low investment, you’ll have more opportunities to practice.
  • Helps you focus on fun When your goal is to impress her and try to win her over, you’re putting too much emphasis on the result. “If I show her I will spend money on her, she will like me even more.” This is a mistake. Women aren’t robots you put “Impressive!” tokens into and get out a girlfriend or sex. Reframe and start focusing on making a date fun for YOU. When I focus on having fun, people around me usually have fun too.
  • You’ll have women flake less These new dates are so low investment, she’s not going to feel overwhelmed. Instead of “I don’t want to be stuck with this guy for an entire movie/show/dinner.” She’s going to think “Oh, it’s just a couple of drinks during happy hour.” or “It’s just coffee.”
  • You will go on more satisfying dates And it all has to do with what dating is like for women.

YES, DATING FOR WOMEN IS DIFFERENT (AND HERE’S WHY KNOWING IS GOING TO GIVE YOU AN ADVANTAGE)

Men, here’s the reality: Dating is different for women than it is for us.

You know how dating sucks a lot of the time for you?

Well for women, it sucks too, but like, Supersized, with a side order of Nuggets, and 2 Apple pies.

Before you scream “Guys have it hard too!”, Remember, I’m on your side. I’m trying to make it suck less for all genders, so hear me out.

You’re probably reading The Essential Man because I seem to know the exact struggles and problems you have when it comes to your style.

I can break complicated fashion ideas down into something you can follow. And it’s a reason why a lot of you love my posts and emails.

How do I do it?

Well, I spend a lot of time talking to you guys, asking you what your style challenges are, through emails, surveys, jumping on video calls, even taking a few of you out for coffee.

I want to know what’s working. What frustrates you. Why you even want to dress better in the first place.

With that knowledge, I can better understand how to write advice that resonates with you and connects.

In short, I have a little empathy to see where you’re coming from.

The reason young Peter was terrible at dates was precisely this reason: I had a severe lack of empathy.

The first dates were really all about me. Dating was about what I could get out of it.

“How can I impress her.
“How can I get a second date.
“How do I get her to kiss me?
“How can I make her my girlfriend?

This is probably your problem too on some level.

Whether it’s getting women who flake, coming off as creepy, or not getting dates at all, empathy is going to help your dating game more than any pick-up line or style hack I can show you.

MY FAVORITE WAY TO UNDERSTAND WHAT DATING’S LIKE FOR WOMEN

A while back I tested out a dating program with my friend Caleigh, a dating profile makeover specialists.

One of the first exercises for our guys involve showing them first hand what it’s like to be a woman on a dating app.

Here’s what we had them do, and here’s what I want you to do this week: Go to a few women in your life, friends, coworkers, sisters, people who are around your age and use dating apps.

Ask them to see their inbox.

I bet it looks MUCH different than yours.

Here’s my guess at what you’ll find:

  • She probably has 10x more messages than you do
  • 75% of those messages (or more) have something to do with her looks
  • 75% of the messages about her looks also includes something vulgar
  • She more annoyed with the app than you are

Can’t find anyone that will share their dating app inbox with you?

I give you permission to break the TOS on this one and create a temporary fake account as a woman. Upload a random picture of an average looking woman, say, a 7 out of 10 (so you can’t say “It’s only cause she’s hot!”) And fill out some general details in the profile.

And now, prepare yourself for the onslaught of creepers.

Look, we had the guys do this exercise for a reason. It’s the same reason I want you to stop where you’re reading, bookmark this page, and do the exercise right now.

We want to help you understand the shit women go through on a daily basis (See Master of None Season 1 Episode 7) so you can avoid being THAT dude.

So you can have better dates! Better relationships! Better sex!

So you can just be BETTER all around.

So what does this mean for you? It means one of your goals when planning a date, especially a first date, is to make her feel at ease. To feel comfortable. To feel safe. Dating for women, overall, can feel hostile and unpredictable in comparison to what us guys experience. So with that in mind, you need to approach a first date the same way I do with my style advice: with empathy.

Ready to learn how?

Let’s put all this together.

ANATOMY OF A BETTER FIRST DATE

#1 It should be casual

Splurging on Hamilton tickets for a first date? Baller, but way too much for someone who is basically an attractive stranger. Elaborate or expensive dates tend to only impress one type of girl, gold diggers. For any sane, cool, quality woman, it’ll come off like you’re overcompensating for something. So keep it casual. That means no helicopter rides on a first date. (Yes, this happened to a friend of mine!)

#2 Keep it short (but flexible)

Avoid anything that requires a lot of time and commitment – like a dinner or long show. The worst thing that can happen is you realize after ordering your mains that you don’t like each other, and now you’re stuck waiting for your food.

Coffee and walk. A couple of happy hour drinks after work, perfect.

One of my favorite “tricks” is to tell her you have some plans, like dinner with friends but would love to do something with her a couple hours before. And if the date is going well, you can tell her they canceled and keep it going. (Yeah, it’s a bit of a sneaky white lie, but there’s a good reason! More on this later)

The most important thing single women are looking for on a first date isn’t a surprise bouquet of flowers, but a feeling: comfort. Of the women surveyed, 79 percent said they most care about feeling comfortable on a first date, even above feeling happy (35 percent) and liked (27 percent).” (source: Bustle)

#3 Make sure you can have a conversation

No movies. No loud concerts. Hell, no loud bars. You want to be able to have a conversation and get to know each other. If you have to lean into her and shout into her ear, it’s too loud.

#4 Keep it earlier in the day

Women have bad experiences on dates that are later in the night, and it’s usually due to guys trying to be slick and setting a “mood” to hookup.

By planning an earlier date, you’re telling her “I’m not just trying to sleep with you.”

Look, I have nothing against first date hookups. The point of this, however, is to craft optimal, low stakes first date to see if you even like her and if you both are actually compatible. After there’s real mutual attraction, you two can be adults and figure out where to go from there.

3 EASY FIRST DATE IDEAS THAT HAVE BEEN SUCCESSFUL FOR MY CLIENTS

Let me give you a few of my favorite, successful first date ideas I’ve recommended for actual clients:

The Drinker Friendly Date: Happy Hour After Work

The Date
A couple of after work drinks during happy hour at a bar that’s convenient for both of you.

What to tell her
“I have dinner plans Friday at 7:00 with a few friends, but I’d love to take you on a date. Would you like to grab a couple of happy hour drinks after work at The Nomad, say around 5:30?”

Why this is awesome for you
A classic, done right. If you prefer to drink on dates like I do, this helps you relax a bit. It gives you a couple hours to get a feel for her and to see if you two have a connection. If you don’t, no worries, you have an out!

Why this is awesome for her
Let’s break down what you said according to her:

“I have dinner plans Friday at 7:00 with a few friends, but I’d love to take you on a date.”

He used the word date, not grab some drinks, not hang, so there’s no confusion as to what this is. It’s a date! Which means he’s interested on some level.

“Would you like to grab a couple of happy hour drinks after work at The Nomad, say around 5:30?”

He has plans at 7:00, which means if the date sucks I don’t have to try and awkwardly find a way to leave. It also says he’s not trying just trying to sleep with me, which a lot of guys tend to do when they plan a date for late at night.

He also gave me a specific place, day, and time, which means he’s a grown man that is responsible and can make a real plan. That’s sexy.

No Alcohol Required Date: Coffee and a Walk

The Date
Grab a coffee and take a walk somewhere nice with people around, like a farmers market.

What to tell her
“I have some errands to run Saturday around 4, but I’d love to take you out on a date. Since you don’t drink, I thought it would be fun to grab some coffee at Blue Bottle and take a walk through the farmers market. There’s this stall that has some amazing apple cider donuts you’d love. Are you free around 2pm?”

Why this is awesome for you
Whether you’re young, not much of a drinker, or sober, a coffee date is one of the best first date options you can offer. It’s a really low investment date not only time-wise but financially as well. A stroll somewhere, like a park loop or farmers markets, should give you enough time to find a connection. Don’t forget to stop on occasion to take in a sight or try something interesting from a local vendor.

Why this is awesome for her
Let’s break down what you said

“I have some errands to run Saturday around 4, but I’d love to take you out on a date.”

Again, using the word date makes this clear as to what it is. This is especially important for dates on the more casual side, like coffee, which can often be confused for just “hanging out.” By saying the word date, you are setting the expectation that there is a romantic context.

“Since you don’t drink, I thought it would be fun to grab some coffee at Blue Bottle and take a walk through the farmers market. There’s this stall that has some amazing apple cider donuts you’d love. Are you free around 2pm?”

First, you showed that you paid attention to the fact that she doesn’t drink, and that you have some empathy by planning a date that doesn’t involve drinking.

You’re clear with a location, time and activity, which she’ll appreciate because many guys make the mistake of being vague. Bonus points for showing her why the date is a good idea, like mentioning fantastic apple cider donuts.

The most important thing on a date for a woman isn’t where you take her or how much you spend, but being comfortable. By setting a time frame (“Date starts at 2pm, I have errands around 4pm.”) You’re signaling to her you don’t want to just hook up and she knows she’s not gonna be stuck with you in a dark bar at 11pm if you end up being a creep.

Bonus: My favorite date: Covert day drinking and a walk

The Date
Combine the two for a fun twist. Covert day drinking and a walk! Grab a coffee drink at Starbucks, spike both of your drinks with a bit of bourbon, and take a walk somewhere nice with people around, like a farmers market.

(I recommend a vanilla latte with a bit of Bulleit Bourbon)

What to tell her
“I’d like to take you on a date, but I’m kind of bored of all the bars. Would you be interested in grabbing some Starbucks cups with me, filling them with some adult beverages, and taking a walk through the farmers market? Say Saturday at 2?”

Why this is awesome for you
I love this date because it’s a break from the usual coffee or bar date. It’s a combination of both, with a bit of spin. There’s nothing funner than getting a bit buzzed in the daytime, especially secretly and on a date.

Why this is awesome for her
Let’s break down what you said in her eyes:

“I’d like to take you on a date, but I’m kind of bored of all the bars. Would you be interested in grabbing some Starbucks cups with me, filling them with some adult beverages, and taking a walk through the farmers market? Say Saturday at 2?”

He wants to take me out on a date. He’s tired of bars? So am I!

Day drinking! Secretly out of Starbucks cups? Fuck yes! That sounds so fun!

WHAT TO DO AT THE END OF THE DATE?

About that little white lie…

Alright, so you might notice that many of these prepositions start with you saying you have plans, but would like to meet up earlier for a date.

Technically you’re fibbing a bit, but for a good reason. You’re giving both of you a way out if the date sucks, and you’re putting her at ease by letting her know she’s not going to be stuck with you all day if you two aren’t clicking.

I wouldn’t call this manipulative, but somewhat beneficial to both of you. If you feel bad about “lying,” then I suggest you make some actual loose plans with your friends for after the date, but let them know you might bail if the date goes well.

If the date sucks for whatever reason (You’re not into her, she’s clearly not into you, she says something super racist and not in a joking way…)

Easy, you have an out. You already let her know you had plans for after the date, so there’s no need to try to think of an excuse.

If you want to bail early, pretend to check your phone and read a text from your friend, informing you they’re going to dinner early. Apologize for the short date, pay for your drinks, and leave.

If the date is clearly going well (Awesome!)

You have two options.

First, you can stick with the story, call the date a success, ask her out on date #2 while the iron is hot, and leave. Easy.

The second option, and my favorite, is to keep the date going. Here’s what you can say:

“Hey, I’m having a lot of fun with you, and I’d rather keep this date going. Would you like to head to this spot nearby for a bite? They have some amazing tapas.”

This is a great option to turn a short test date into a real proper date with a lot of chances to have fun. It helps to have a few places in mind beforehand nearby.

Sometimes your date will feel bad about making you cancel with your friends, but if you say something along the lines of “I always see my friends, and I’m actually going to have dinner with them again Monday. “ It’ll be fine.

(Note: If she insists you not cancel on your friends, take it as a sign she doesn’t want to keep the date going, and that it’s not going as well as you think.)

SPEED ROUND! FIRST DATE Q&As

What do I wear?

Read my post “I asked 101 Women What a Man Should Wear on a First Date”

How many drinks should I have?

Limit it to 2. You want enough to relax and have a good time. This isn’t a frat house rager. This is my personal rule, but it also happens to be what women prefer.

Who pays the bill?

Offer to pay, if she insists on splitting it, split it. Don’t fight it dude, you’re getting a date for 50% off.

If you arrive early

Text her and let her know you’re early and where you’ll meet her (outside, at the bar by the big painting, a table by the window, wearing the leather jacket).

My wife once told me about a guy she went on a date with when we were casually dating.

He arrived early, didn’t let her know that he was sitting at the bar, didn’t save her a seat, and was already drinking. Let’s just say her decision to choose me over him was a no-brainer. Don’t be that guy.

If you’re going to be late

Text her. Make sure you anticipate it. If you’re supposed to meet at 6:00 and it’s 5:45 and you’re stuck in traffic, text her. Let her know the situation and give an ETA. Even if you make it on time, send her a text and say “Hey, I’m stuck in traffic right now, I might be a bit 5-10 minutes late.”

Even if you end up showing up on time, it’s a bonus!

DATING ISN’T EASY, BUT IT DOESN’T HAVE TO BE HARD

To recap:

  • Use the word DATE I want to drill this in your head, you need to use the word date so there is no confusion. Half of my clients dating problems all stem from the fact that they weren’t clear with their intentions. By telling her “I want to take you on a date” (not hang out, grab a drink, chill), you are telling her “I am interested in you romantically.”
  • Keep it casual Low investment for both of you. The goal isn’t to find your life partner, the goal is just to meet another person, grab a few drinks, see if you like each other, and maybe do it again.
  • Give it a time limit Tell her you have plans later in the day, but would love to take her on a date a couple hours before. This serves a few purposes. It makes her feel comfortable and at ease – she knows she’s not going to be stuck on bad date. It gives her an out. It also gives you an out if she ends up sucking.

The one thing I want you to take away from the post is this: women are still pretty much the same as you.

They deal with flakes, boring dates, and people who are nothing like their profiles. They’re worried about not being liked. They’re worried about having their time wasted.

Better dates really all start with you.

If you can lead the way in going on more of these micro first dates, focusing on making her feel comfortable, and emphasizing fun and conversation over being extravagant and expensive, you’re going to make it a little more enjoyable. Hopefully for the both of you, but at least for yourself.

peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here