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THE ULTIMATE GUIDE TO ONLINE DATING: Tips, tricks, and manipulations to navigate the pains and pitfalls I looked at her and then looked at the dinner bill.

She looked me directly in the eyes and smiled.

Still, no response.

It definitely wasn't my best moment, but it was not hers either.

Apparently, as I found out later, I had fallen into a trap called"the meal plan." The meal plan, if you're unfamiliar with it, is when women go on dates with guys merely to get a free meal. It was obviously quite popular with attractive college girls, a classification she definitely fell into.

When I first heard about the"meal plan," I did a mental rewind as I scrolled back through all the dates I had gone until there: all 37 dates to be precise.

Of course at first I was outraged.

How could women take advantage of me like this? Especially since I was being so vulnerable by putting myself out there to ask them out in the first place.

As I matured in my internet relationship, however, I realized that this was really a reaction for what men do to women.

There are 3 significant levers in our lives that, if we pull on them properly, can change everything. Our career, our health, and our relationships can be the difference between depression and elation.

I discovered this firsthand because in the past five years I went through the excruciatingly painful and draining process of pulling all three levers at once.

I stopped the career I had been building for over 7 years and I left my 10-year relationship with my girlfriend who I thought I was going to marry.

All of a sudden I was a career and dating newcomer. I was scarred.

After 9 months of misery and frustration I was going to give up on online dating all together. And then, for some unknown reason, my ambitious gene activated and a little voice in my head said,"you're going to give up? No, no you're not. You are going to kick online dating's ass!"

I began to channel my misery into anger, and my anger into determination. I began to approach online dating just like one big experiment. I started creating what I called,"The Process."

In this blog post I will take you through the whole process I chose to master online dating. By optimizing your profile, A/B analyzing your descriptions, starting meaningful conversations, as well as crafting interesting dates.

We'll go over how to streamline the online dating process so that you can not only get dates, but maybe discover the love of your life (with minimal stress).

Now, before I get into it, I should preface that based on your context, your culture, and your comfort, your process may need to be different than the under. But, the important takeaway here is to pull back the emotions that come

from dating and treat it like an experiment.

If you approach it with the mindset of,"I will go meet interesting people and do interesting things," you will be more inclined to enjoy the procedure. And, if you're diligent, you might end up finding that special person.

UPDATE: As of 2019 I've been with my new girlfriend, who I met on OkCupid, for 4 years and we have moved in together. So maybe these strategies aren't all that crazy, but perhaps they are, I'll leave it for you to judge.

Listen to the Modern Dating Show Podcast for more tips, tricks, and embarrassingly real stories.

Note: You can also listen to the Modern Dating Show podcast, where my friend Trevor and I pay a lot of these strategies as we browse the present struggles and embarrassments of his own dating journey (and answer listener questions).

STEP 1 -- Decide what you're looking for The complete most common mistake I see both guys and gals making when it comes to online dating is they don't define their target clearly. Deep down inside, the majority of us know whether we're looking for a serious relationship or just to have fun.

The more common scenario that I've found is that both women and men who are searching for a meaningful relationship are optimizing their dating for fun instead.

I remember how one day when my coworker, Maddy, heard about my success with online dating, she asked me to assist her with her OKCupid profile. She's an incredibly smart and capable woman and she's' really beautiful, a real 10 out of 10, so I was confused why she would need my help. Basically, in order to maximize for receiving dates, Maddy had chosen to just include her most provocative photographs.

Now I want to be clear, there's nothing wrong with girls having"promiscuous" photos online. The problem, in the event of dating, is the arrangement of a dating profile and what you contribute with.

Our brains have evolved over centuries to intuitively pick up on visual cues much faster than written hints. In actuality, they've found that men that are even walking with their girlfriend, will reflexively look if an attractive woman walks by activating their conscious brain.

Because dating profiles hide most information other than the profile photo before a user clicks, resulting in provocative photos sets a poor first impression.

So, while it's totally fine to have sexy photos up in your instagram, leading with them in your online dating profile is sending signals that may be attracting the wrong type of guy. Additionally, there are plenty of classy ways to have interesting pictures that speak to more than just the subconscious mind.

Online dating pictures can be both intriguing and classy

So, although Maddy was attempting to find a relationship, her photos were sending signals that she's looking for"fun." Understandably, she had a line of douchebag guys filling up her inbox.

For men, we tend to have the opposite issue.

Every man who has done online dating will attest to the struggle of getting a girl to swipe right in their profile, let alone to get them to participate in a conversation.

Guys, this is entirely your own fault.

I have seen guys spend hours talking about the numbers of their favourite sports team, which player has what stats, who's health is suffering, and even how financial reports will influence the team's chances.

However, when it comes to online dating, guys tend to slap a few pictures on their profile and then start swiping like orangutans until their palms develop calluses.

Men, stop.

Before you start creating or re-creating your dating profile, stop and think about what you're trying to achieve.

Are you trying to date a lot of people?

Or are you trying to find a meaningful relationship?

And"both" isn't an answer. As the saying goes...

"If you try to appeal to everyone, you will interest no one."

The techniques I will outline below work for either desired outcome, but the choices you make will vastly affect your"conversion" rate.

For instance, the first time I mastered everything in this process, I started going on a lot of dates (3--4 per week, weekly ), but I still felt incredibly unfulfilled.

I just realized months later that, while it is good to go on a great deal of dates and get practice relationship (remember I had been off the dating scene for 10 years), it was even more important to be sure I had been dating the perfect people.

Luckily I realized this before I was the victim of any more"meal plans."

STEP 2 -- A/B Test your online dating profile pictures and descriptions According to a study from Princeton, it's estimated that in any relationship, whether its social or work, we make up our mind about whether we like the person in less than one second.

The single biggest flaw in online dating is the first impression you make is based solely on your profile picture.

They do not get to hear you speak. They don't get to shake your hand. They do not get to smell you (it is a thing).

All you get is one picture and there is a 99% chance it's the wrong one.

If one is coming online dating as an experiment, naturally the first thing to check is the profile picture. I started

this process in a very unscientific way...

I went to every female friend I knew and asked her what she thought of my pictures.

One hundred, and I mean 100% of these said that my first image wasn't my best.

It was interesting feedback, but I was not sure how I could test multiple pictures considering I could only put one as the default.

The answer: testing across programs.

I created profiles on Hinge, OKCupid, CoffeeMeetsBagel, along with the dreaded Tindr.

I retained my profile description the same on every profile, but I put up a different profile image on each. I rotated the pictures across profiles before I could get a big enough sample size and be certain that the platform wasn't effecting results.

Four of my actual dating profile pictures Sure enough, the profile picture which I thought was my best was always the one with the least games.

Interestingly enough, a picture I did not read much into, pic B, was actually a massive turn off for pretty much 100% of girls. When I asked them why, without skipping a beat they replied,"it makes you look like a player."

I was shocked when I found this out, because the two girls in that photo are really good friends of mineso that I never would have made that connection.

Sometimes your photos can be your biggest blind spot.

To completely test this idea out, I actually enrolled a couple of friends (both men and women) into the experiment and had them change out their profile pictures.

They got varied results, but one thing was consistent: the picture they thought was their best, never performed the best.

Listen to The Modern Dating Show Episode 2 This is a super simple optimization that can look like a pain now, but it is going to save you from dozens, if not hundreds, of missed matches.

This is the 20% of work that will get you that 80% improvement in results, so please rotate your photos and rotate them often.

Top Tip: If you want to speed up this process, you can actually ask your matches exactly what they think of your own pictures. If a conversation with a match was not going well, I decided to get some"user feedback" by asking her why she swiped right and which of my photos she thought was best. (I also used this technique to ask recruiters why I was not getting jobs.)

Now, a part of this error might be my fault, since I took his advice quite literally. I began to speak my mind, dress how I wanted to dress, and act how I wished to act.

This turned out to be a horrible idea.

Without any filter or thought behind my actions, I rubbed more than a few people the wrong way.

Now that I have matured a bit, I have come to realize that there's a difference between being your total self and being yourself.

Whether we like to admit it or not, we're never our total selves except when we are by ourselves.

Seth Godin has a great podcast on"signals," which you can listen to here. In the podcast, he explains that we actively choose which signs to give to other men and women. A guy wearing a button up shirt, for example, isn't necessarily wealthy, but the button up shirt is putting out the signal that he's wealthy.

Much like someone who wears all black and an anarchy necklace is indicating she does not want to follow society's rules, the guy in the button up shirt is indicating that he is okay with following convention.

Signals matter.

In college I met a girl at a party who immediately caught my attention. She was wearing a summer dress, flower earrings, and looked really cute. I approached her and we immediately hit off. We spent the whole party flirting and dancing.

We made plans to have a lunch date at the college cafeteria later that week.

I got to the cafeteria early and chose to save us a booth seat. As I was waiting, a woman walked up to me and smiled. I looked up and saw a cute girl dressed all in black, wearing black eyeshadow and an anarchy necklace round her neck.

At first I did not even recognize her, but after a few baffled blinks with my eyes I realized it was my date.

She sat down and we started talking.

I was that man.

I didn't care what she dressed like, but as we picked up our conversation we soon realized we had practically nothing in common. The outfit she had used as a signal at the party didn't match her personality in any way. We ended the date cordially and proceeded on.

Signals matter.

Choosing your signs is good, but picking false signals not so much.

The same goes for your online dating profile description.

You don't need to lie, but you also don't want to be your total self. You need to tell them about how you collect vintage records, you do not need to let them know about how you cry every time a U2 tune comes on. You want to tell them about how you volunteer at the animal shelter, you do not need to tell them about how you ran over your cat.

First impressions matter.

Crafting a fantastic description is perhaps the most difficult and personal piece of enhancing your online dating profile. There is absolutely no right answer, but there are definitely some wrong answers.

The first step to having a great dating profile description is using a clear structure.

I break down a dating profile description into 3 parts: Headline: A short sentence somebody can read quickly.

Intro Paragraph: A bit longer description that provides some color to your interests and personality.

Call to Action: A desirable action you want them to take. Online dating is inherently awkward, so help another person by letting them know something that you two can talk about. Ladies this is particularly true for you. If you don't want men messaging you"hey" or"wanna f*ck?" Then give them some fuel to begin the conversation with.

Unfortunately, people tend to surf online dating apps the way they surf social networking sites: quickly and without much thought. It might be, in fact, that mobile devices have trained us to browse everything in a similar way.

Due to this, I think the headline is perhaps the most important bit of your description and you need to try different variations until you find one that works for you. After a lot of testing I found that this one worked best for me: The objective of the headline is to provide a quick snapshot of what is unique about you. Having a headline that's authentic, interesting, and short acts like a stop sign for the person who's scrolling through the dozens of profiles on their phone.

If you ask any top-performing marketer,"how do I create content that will be successful?" Chances are they'll laugh at the question.

As any good content marketer knows, great content is about respecting the medium that you are creating the content for. By way of example, if I went into a woman at a bar and said,"Outdoorsy, curious, ambitious, active," she'll definitely get up and leave.

The opposite is true for online dating, however.

You want your headline to be fluff free. Keep it to a 3--6 words, or one sentence, and be sure that it is quintessentially you.

After that initial curiosity is peaked, you should begin paving a path towards them getting to know you a little bit more.

This isn't the time to compose a novel about yourself. After all, this is only your 3rd touch point with this person, your picture and headline being the first two.

The intro paragraph gives a small amount of colour and possibly some talking points that you can talk about in conversation (again, ladies, this is extremely important to add if you want to have more meaningful conversations).

The intro paragraph that worked best for me was: "I love being outdoors as much as possible! Some of my favourite items are surfing, climbing, and playing

volleyball. I'm a creative at heart but I love learning about businesses and new ideas. I'm into photography, layout, and Tim Ferriss.

My ideal Saturday is playing volleyball at the beach with friends. My perfect Sunday is reading a good book at Promenade cafe."

This paragraph outlines a few basic hobbies and activities I enjoy as well as some non-standard things like business, design, and Tim Ferriss that might peak curiosity.

The main thing to remember about this section is to avoid the generic actions that could apply to pretty much anyone.

"I enjoy hanging out with friends, watching films, binging on Netflix, and going on hikes."

While I'm sure there are people on earth who don't like watching movies or hanging out with friends, probably 95% or more of the people in your area enjoy both those things too.

As opposed to trying to fit in, attempt to stand out.

Try to balance your description between things most people like, so it's possible to find common ground, but also things which are uniquely you.

For instance in my description above: -- Many people like being outdoors and photography.

-- But very few people like learning about businesses or Tim Ferriss.

The Call To Action This is optional, although it certainly helps. In marketing, a call to action (CTA) is the action that you want the user to take after they've viewed your content.

In dating, you essentially want the individual to message you. This seems like a no brainer, but I've found that a lot of people, both guys and girls, have been rejected so many times that they finally become discouraged from making first contact.

I've heard countless stories of women who have paired with a guy who they really enjoy, but the guy never messages them. When I ask them why they do not message first, it is said that they don't know what to say or they do not want to appear desperate.

The call to action helps alleviate this problem by making it clear that you want them to message you.

But, obviously you do not want everyone to message you, so make your call to action specific.

On OkCupid they have an individual section that says: My CTA goes as follows: "You should message me if you are an interesting person who likes to play outside."

Again, as with this advice, when in doubt just test it out. Try using a call to action and see whether your conversations improve. If they don't, just delete it.

The attractiveness of dating apps is that instead of having 1--5 chances to make a relationship, as you would if you went to a bar for example, you have tens of thousands of chances and"do-overs" to play with.

STEP 3 -- Making first talking and contact The place where online dating falls flat on its face compared to"in real life" relationship is when it comes to the conversation. Having to talk online as your first conversation is a massive limitation when you are trying to start a new relationship.

For starters, it is a really unnatural method of communicating, since it's been proven that we receive 55 percent of our communication from non-verbal (or in this case non-typed) communicating.

It is logical then that if you take millions of people and set them in a supernatural communication environment you get some pretty unnatural conversations.

While it might be fun to play around with weird conversation openers, if you're serious about finding a good relationship through online relationship, then it is a good idea to research your results a little bit. This gave me the chance to begin testing different conversation openers and see patterns that I just wouldn't have been able to see if I didn't have a high match rate.

Listen to The Modern Dating Show Episode 6 I will spare you some of the terrible ideas I had, but in the spirit of good fun, let's examine how well you can judge a fantastic opener from a bad one. For bonus points, try to order them from most effective to least effective.

How's it going?" How was your weekend?" (or some other variation of the type of question). How did you like X book?" (according to a book they listed in their profile) I'll let you think about it for a second.

(I'll add some distance before the reply below. Scroll once you're ready.)

Scroll for the answer

Scroll for the response Scroll for the response Scroll for the response Scroll for the answer Scroll for the response And the answer is...

If you guessed D, then you picked the best answer! (If you guessed C, you chose the worst response.)

In order of best to worst, the answers are D, B, A, C (D being best).

There are pluses and minuses to any conversation starter. While I found that the absolute best conversations resulting from"Hey! How did you like X novel," that clearly depends if they have put a book in their profile.

You can alter this to ask about some other part of the profile, like a picture or a place in their pictures. The reason I guess that the book one works best though is because a) it shows you actually read their profile and b) it indicates that you read.

If I can use the book opener to start a conversation I typically also extend it to,"Hey! How did you like x publication? (This is the way I opened the dialogue with my now-long-term girlfriend).

Pretty much every conversation I started with this opener felt much more natural and moved beyond a few messages.

The next best option,"Hey! Works nearly as well, but it is obviously limited to Sundays, Mondays, or Tuesdays. (It would be strange if you used this on a Friday). This worked pretty well, but not nearly too. I suspect it's because it seems too much like I'm going to ask her on a date or it puts her on the spot to think about something interesting.

The Do's & Don'ts of Online Conversation Now that you've made contact and another person has responded, it is time to have a conversation. Every dialog changes, but there are a few guidelines that I'll put in here as hints.

First, some online dating suggestions for guys: DON'T attempt to be interesting by being obnoxiously weird. I can't tell you how many messages my female friends have shown me that noise objectively psychotic. The sad thing is I know that the man is just nervous and trying to think of something interesting to say. Just have a regular conversation like you want a friend.

DO try to talk about things she's interested in but also add your own thoughts. One of the most common complaints I've heard from female friends is they feel like they're being interviewed. Be sure that you ask questions, but that you also discuss things about yourself in equal measure.

DON'T make comments about her body or appearance. Regardless of how well intentioned you are, it will be perceived in the wrong way. Saying things like,"you're so beautiful! You've got a cute smile! You're..." will only

result in a polite"thank you" and won't create meaningful conversation.

Now, a few online dating suggestions for women: DO be nice and help direct the conversation. Even when I have tried to be nice and friendly, I've still received quite curt or standoff-ish answers. No matter how much men pretend that they don't care about the dialogue, they do.

And they normally have no clue what they are doing, so offer them some help and guide the dialogue in a positive direction.

DON'T answer questions without asking any of your own. If you're tired of conversations feeling like interviews, then be certain to ask the man about things he is interested in also.

DON'T make conclusions too soon. In my experience women have a tendency to place a lot more thought into their text messages than guys do. If a guy says something that looks weird or strange, give him the benefit of the doubt and do not read too much into it, chances are he didn't either.

Now a suggestion for both parties: Try to move the conversation from online to in real life relatively quickly. Online dating is a excellent tool to fulfill someone, but it's just that. It's a tool, it isn't actual dating.

My general recommendation for moving from online to in real life is either one long conversation or two brief conversations. It should never take more than a week to establish a date. Thus, if you match with one another on a Monday, you should definitely have started talking about using a date by Wednesday.

So yes, use the apps, but also get them off quickly. In real life is a lot more fun too in case you know how to set up good dates...

Step 4 -- Making a date sequence that will cause you to smile more and sweat less After I had mastered the online portion of dating, I soon realized that securing the date is just half the battle. The second half of the battle, how well goes, is largely determined before you have even set out from your house.

Where you have your date decides about 50--70 percent of the outcome of the date.

But a question...

Where is the worst place to have a date?

As it turns out, it's actually at the most frequently selected dating location: A sit-down restaurant.

Initially I was taking all my dates to restaurants for dinner. But remember, I was totally new to relationship so I was just following what I had seen in movies.

Many of them didn't go well, but I wasn't sure why. After a dozen or so embarrassing (and expensive) dates, I decided that I should experiment with some other locations.

What happened next was totally mind blowing.

It was not I was doing anything differently or that I had been choosing better women to go on dates with, it was merely a matter of context.

Here's why I think dinner dates do not work, it goes something like this: You meet a complete stranger out a restaurant. You sit down at a desk. You begin talking, then the waiter interrupts asking about drinks. You continue to speaking. The waiter interrupts again to your food order. You are not ready to order since you have been talking. The waiter gives you"another moment." You examine the menu making remarks about the choices. The server comes back ten minutes later. You continue talking. You talk and talk. Then you run out of things to discuss. What do you do next? You need to keep talking. Talk... Talk... Talk!

A dinner date provides no choices. It's a singular task that depends on you linking with a complete stranger almost instantly.

This problem is exacerbated by the fact that most of us are getting worse at having in-person discussions.

Spending so much time online has enhanced our written communication skills, but it has also atrophied our inperson communication skills.

Therefore, if we are getting worse at having in-person discussions, why would you bet your entire love life on the fact that you'll be able to have an remarkable in-person conversation with a complete stranger?

3 Rules for Creating Great Dates I never thought that relationship could be a life-or-death action, but one day changed all that. I was holding on to a small ledge, about the size of a golf-ball, while the rest of my body dangled 30-feet over the ground like a giant cat toy.

My fingers began to sweat and I knew that I couldn't hold on to the ledge much longer. "O well," I thought,"this will be a good bonding experience."

As I let my fingers slip off the ledge I anticipated the sharp jolt of the rope in my climbing harness. However, there was no jolt. I started falling for what felt like eternity.

As it happens, my climbing partner had let go of the rope just as I'd slipped off the ledge. She panicked and didn't grab the rope until I had dropped 15 ft to what I was sure was my forthcoming death.

Finally the rope eventually stopped and I felt a massive jolt, both physically and emotionally.

My entire dating profession made a 180-degree turn once I began taking my dates on fun activities instead of dinners.

A number of these activities worked better than others. However, I found out that the most crucial elements to a great date place could be distilled into three classes: Walkability -- Do we need to sit together or can we walk around? When you are walking, your landscape is changing so that you can pick up new conversation topics as you go. "O look at that naked man on rollerblades!"

(It is San Francisco after all).

Action -- Can we both do the activity reasonably well? I've seen guys get this one fairly wrong. It's fun to teach someone something that you are passionate about, but make certain it's not too hard. Taking a woman rock climbing? Make sure she isn't scared of heights first.

Scalability -- Can the date grow or shrink in scale as needed? Having a terrific time? Great! Let's go get dessert! No

chemistry? No issue, how do we end the date sooner?

Using these three criteria, I crafted a 3 date sequence that nearly doubled the number of successful dates I went on.

Now I know what you're thinking,"This guy took women out to the same areas like it was some sort of regimented assembly line?"

This was my go-to order, but, depending on interests, I'd substitute different activities to keep the dates interesting. This was merely a template that simplified my choices and decreased the cognitive load I was putting on my brain.

So here is my ideal dating arrangement:

Date #1 -- Off the Grid: Off the Grid is a gathering of food trucks each Friday by the San Francisco bay.

Why I like it: One of the difficulties of inviting someone out to dinner is that everybody has different food tastes.

Then (if you are a man ) you have to account for cost of food. Off the grid solves this since there are over 20 distinct types of (affordable) cuisine. Additionally, it lets you walk around, people watch, and get drinks. It is possible to extend the date by getting dessert or listening to the live bands. Feel like going all out? Queue the awkward white-boy dance moves.

Date #2 -- Variable: This date could vary based on interests but I had a few go-tos, namely: Little Italy, rock climbing, tennis, picnic on the shore.

Why I like it: What these activities had in common were the 3 factors: walkability, activity, scalability. We could walk around Little Italy, grab cannolis, stay for drinks at Jack Karouac's favorite pub, or abort early. With both rock climbing and tennis we could alternate between activity and talking. If we did a picnic on the shore, we could go for romantic walks or huddle around a fire pit on Ocean Beach.

Why I like it: This date was particularly important because if a woman had made it to date #3, it meant I actually liked her. Additionally, it meant we might take the relationship to the bedroom. The Cal Academy night fulfilled all requirements, plus it was a semi-formal occasion so we could both dress well for that particular night. This was also my secret test because if a woman did not like facts and science it likely would not work out between us anyway. As an added bonus, it was also a 20-min walk from my place, so that helped with the"scalability" of the evening.

Listen to each of the episodes of The Modern Dating Show These are merely three examples of how to take online dating offline and make a reasonably successful dating arrangement. Here are a few ideas on what to look for on each date as you try to make your own dating arrangement:

Date #1: Look for a casual environment that isn't intimidating. Dark bars or loud places don't make for good conversation. Be sure that you can reliably go to this place, so avoid places with long waits or where you will need to make reservations. Ensure you are able to schedule the date for a weeknight (try not to book someone's weekend for a first date).

Date #2: Website link You have broken the ice and you've both agreed to a second date, so have fun with this one! Choose an activity you'll both like that is not too difficult. Avoid intimidating actions like karaoke, group sports, or water skiing. Ideally choose an activity that has a cadence where you alternate between doing something and talking. Going on a 10 mile run is fantastic for exercise, but it doesn't allow for conversation.

Seeing a movie at a movie theater has similar limits.

Date #3: You both confirmed you like each other, it is time to take it to the next level. Try to make this date a bit more special than the first two. It needs to be romantic, it should test how compatible you really are, and it should confirm whether or not you want to continue seeing each other long term. After the excitement of dates one and two, there may be a lull in date 3, so be sure whatever you select gives new intimacy to the relationship. For example, if I did not go to the Cal Academy I'd go dancing instead.

STEP 5 -- Obtaining your Timing Right maybe one of the most important pieces of the internet dating mystery that I see guys screw up again and again is time. Assuming the guy is the one forcing the relationship sequence (which isn't necessarily the case) there are some questions you need to ask: When should you ask her to go on a date?

Here I'll share my answers to these questions that I've found most useful. But again, depending on your context, your culture, and your own comfort your answers may vary. I will share my experience (as a heterosexual man living in San Francisco) and you can make whatever adjustments you deem appropriate. The main thing is to actually consider timing, rather than leaving it up to"feeling."

Going from Online to Offline It's very easy to let a great online conversation die out. You message her, she messages you, back and forth, back and forth. In order to make certain I do not waste all my time with online conversations I found that it was best to ask a girl to go on a date after about 2 days of messaging or about 20 minutes of continuous conversation.

Again, try not to linger in the safe-space of the virtual world too long. It might feel like it's necessary, but it is quite easy to waste a lot of time and momentum in the chat room.

Going from Date 1 to Date 2 When I was 25, working as"the new guy" at a tech startup, my desk was placed right behind the sales staff.

One thing I discovered is that every time they were finishing a call they would ask,"okay so what does your calendar look like for next week? Busy? Okay how about the week then? O that's no great also. Okay how about the week after that?"

No matter what the prospect said, the salesperson would insist on at least"penciling" another meeting to the calendar with the option of cancelling if needed.

When I took this technique and applied it to dating, it led to some pretty incredible results. This rule is somewhat contrarian, but it has worked really well: Always ask for the second date on the first date.

One of the worst things about dating is that you are putting yourself out there. You're opening yourself up to strangers and in return you're getting plenty of uncertainty.

No one likes uncertainty.

No one likes to look at their phone every hour to determine if you've texted them or not. Nobody likes to wonder whether you like them or not. Surprisingly, most individuals do not mind if you don't like them, they only want to know.

So my suggestion would be to stop playing games, both with the other person and with yourself.

If you like them, tell them you like them.

If you do not, have the respect to let them know you do not. (A gentle way to do this is by telling them that you aren't prepared to date at this time. I had a woman tell me this and it was the simplest let down I've ever experienced and used it later myself also ).

I should pause here for a single caveat: Yes, you should tell them you like them, but not always.

I see this a lot with both guys and girls who get very excited by the person they have just met and then they proceed to text them, call them, and watch them day after day after day.

Stop Chasing Shadows once I was thirteen years old, my grandfather gave me some advice that I still use to this day. He told me,"Girls are like shadows, the more you chase them, the more they run away. The more you run away, the more they pursue you."

If you find someone who you want to be with really poorly, do not frighten them away by being obsessive. If they like you as well, there is no need to chase them. Yes, you should actively try to establish a date, but there's no reason to go on dates each and every night of the week.

Allow the relationship to get some breathing room. A fantastic way to judge if a relationship is going well is if you end up missing the other person and vice versa.

There is a great deal of truth in the saying,"absence makes the heart grow fonder," and now there is even scientific proof for it as well.

In several studies, anthropologists have found that many primates invest more effort into a relationships if the individuals in that connection have been forced apart. What's interesting is that researchers at the Aalto University in Finland have recently confirmed that the same is true in humans.

By data mining mobile phone records and comparing telephone patterns and length, the researchers at the university found that people may also invest more effort into relationships when there is a risk of that connection weakening.

I tried applying this research to relationship in a relatively simple way and, to my surprise, it worked nicely. It turns out that by simply allowing for some time to elapse in between dates, ironically, makes the relationship strengthen rather than weaken.

My cadence for relationship that I found worked pretty well was the following:

Date 1 -- Day 0 Date 2 -- 7 days after Date 1 Date 3 -- 14 days after Date 2 Date 4 -- factor This sequence meant that I would spread out the first 3 dates across a 1 month period. This allowed for sufficient time for the relationship to grow and helped me make sure I did not suffocate my dates, which was especially helpful when I was really into them.

Takeaways and Next Steps As I mentioned at the beginning of this post, these dating approaches helped me tremendously, but based on your context, your culture, and your comfort, your procedure may have to be different than the one above.

The important takeaway here is to pull back the emotions that come out of relationship. In actuality, because relationship is such an emotional activity (like job hunting), it's vital to have a system in place to help you navigate the ups and downs.

By engaging in online dating you're getting on a rollercoaster of emotions and, like on a real rollercoaster, it would be foolish to just jump and continue. Making sure you have that lap belt secured and that you have been on a few less intense rides can help you enjoy the ride a whole lot more.

Perhaps the single most important point to keep in mind though is to let go of expectations and treat the process like an experiment. As we often discuss on the podcast, even when you let go of expectations and only make your goal just having fun with other human beings, online dating becomes something to look forward to rather than something to dread.

Like the help of world wide investors, you want to diversify your portfolio and decrease your chance of catastrophic failure. A means of doing that is by going on dates which are not just sit-down dinners, so that regardless of how your relationship partner behaves, at least you will have a good time doing something interesting.

And, to decrease the risk, you need to build both an outreach and relationship sequence so that you reduce the cognitive load of having to think of new dates constantly. Locate a few activities you like doing and then fit the dates into these activities. This is also a wonderful way to filter out people that aren't compatible with you in the first place, which will save you time and money in the long run.

Of course, regardless of how well I did all of the above things, I had my share of terrible dates. The woman who used me as a meal program being just one of many.

Dating is a rollercoaster that will frighten you, challenge you, and sometimes make you wish you had never gotten on. But remember, when you're feeling down and like giving up on love altogether: "You are not as bad as they say you are, you are also not as good as you think you are."

Take each date as an opportunity to improve yourself. If you constantly work on yourself, improving your discussions, your dates, and your connection with other people, that investment will pay off far beyond online dating.

If you enjoyed this post, I would super appreciate if you hit the green hand clap button below so that more people can discover it. And, if you've any more questions about relationship, listen to our podcast where you can submit your own dating questions and we'll answer them on the show.