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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 straight in the eyes and smiled.

Still, no response.

It definitely was not my best moment, but it wasn't 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 of the dates I had gone until there: all 37 dates to be precise. 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 online dating, however, I understood that this was really a reaction for what men do to women.

Online dating sucks, but...

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

I discovered this first hand because in the last 5 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 connection with my girlfriend who I believed I was going to marry.

All of a sudden I was a career and relationship newcomer. I was scared.

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 triggered and a small voice in my head said,"you are 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 started to approach online dating just like one big experiment. I began creating what I called,"The Process."

In this blog post I will take you through the entire process I chose to learn online dating. By optimizing your profile, A/B testing your descriptions, beginning meaningful conversations, and even crafting interesting dates.

We'll discuss 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 must preface that depending on your context, your culture, and your comfort, your process might need to be different than the under. But, the important takeaway here is to pull back the emotions that come from relationship and treat it like an experiment.

If you approach it with the mindset of,"I'm going to go meet interesting people and do interesting things," you

will be much more inclined to enjoy the procedure. And, if you're diligent, you may 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've moved in together. So maybe these strategies are not all that crazy, but maybe they are, I will leave it for you to judge.

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

Notice: You can also hear the Modern Dating Show podcast, where my friend Trevor and I cover a whole lot of these approaches as we browse the present struggles and embarrassments of his own relationship journey (and answer listener questions).

STEP 1 -- Decide what you're looking for The absolute most frequent mistake I see both guys and gals making when it comes to online dating is that they don't define their goal obviously. Deep down inside, most 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 that are searching for a meaningful relationship are optimizing their relationship for fun instead.

I remember how one day when my coworker, Maddy, heard about my success with internet dating, she asked me to assist her with her OKCupid profile. She is a remarkably smart and capable woman and she's' quite beautiful, a true 10 out of 10, so I was confused why she'd need my help.

The photos I saw in her profile looked like they belonged more on thechive.com rather than on any dating website. Basically, in order to maximize for receiving dates, Maddy had chosen to just include her most provocative photos.

Now I would like to be clear, there's nothing wrong with girls having"promiscuous" photos online. The issue, in the event of dating, is the format of a dating profile and what you lead with.

Our brains have evolved over centuries to intuitively pick up on visual clues much faster than written hints. In fact, they have 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 aside from 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 on your instagram, leading together in your online dating profile is sending signals that could be attracting the wrong sort of guy. Additionally, there are lots of classy ways to possess interesting pictures that speak to more than just the unconscious brain.

Internet Dating pictures can be both classy and intriguing So, although Maddy was trying to locate a relationship, her photos were sending signals that she is searching for"fun." Understandably, she had a line of douchebag guys filling up her inbox.

Listen to The Modern Dating Show Episode 4 For men, we tend to have the opposite problem.

Every man who has done online dating will testify to the battle of getting a girl to swipe directly in their profile, let alone to make them participate in a conversation.

Men, this is entirely your fault.

I've seen guys spend hours talking about the statistics of their favorite 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.

Guys, stop.

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

Are you trying to date a great deal of people?

Or are you searching for a meaningful relationship?

And"both" is not an answer.

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

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

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

I only realized months after that, while it's great to go on a lot 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 right folks.

Fortunately I realized this before I had been the victim of some more"meal programs ."

STEP 2 -- A/B Test your online dating profile pictures and descriptions According to a study from Princeton, it is projected that in any relationship, whether its work or social, we make our mind up about whether we like the person in less than 1 second.

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

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

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

If a person is approaching online dating as an experiment, naturally the first thing to test is the profile picture. I first started this process in a very unscientific way...

One hundred, and I mean 100% of them said that my first image was not my best.

It was interesting feedback, but I wasn't sure how I could test multiple pictures considering that I could only put one as the default option.

The response: testing across programs.

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

I retained my profile description the same on each profile, but I put up a different profile picture on each. I rotated the pictures across profiles until I could find a large enough sample size and make certain that the platform was not effecting results.

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

Interestingly enough, a picture I didn't read much into, pic B, was actually a huge turn off for pretty much 100 percent of women. When I asked them why, without skipping a beat they answered,"it makes you look like a player."

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

Sometimes your photos can be your greatest blind spot.

To completely test out this idea, I really enrolled a few friends (both men and women) into the experiment and had them change 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 to be 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 would like to speed this process up, you can really ask your matches exactly what they think of your pictures. If a conversation with a game was not going well, I decided to get some"user comments" 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 wasn't getting jobs.)

Descriptions are negotiable In highschool I had a history teacher, Mr. Hernandez, who gave me the worst piece of advice I've ever received:"just be yourself" Now, part of the error might be my fault, since I took his advice quite literally. I started to speak my mind, dress how I wanted to dress, and act how I wanted to act.

This turned out to be a horrible idea.

With no 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 understand that there is a difference between being your total self and being yourself.

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

Seth Godin has a wonderful podcast on"signals," which you can listen to here. In the podcast, he explains that we knowingly choose which signals to give to other men and women. A man wearing a button up top, as an instance, isn't necessarily wealthy, but the button up shirt is putting out the sign that he's wealthy.

Much like someone who wears all black and an anarchy necklace is signaling she doesn't want to follow society's rules, the guy in the button jak poderwac kobiete up shirt is signaling that he's okay with subsequent convention.

Signals matter.

In college I met a girl at a party who immediately caught my attention. I approached her and we instantly hit off.

We spent the whole party dancing and flirting.

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

I got to the cafeteria early and decided 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 around 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. After some awkward conversation, she explained that her friends were sick of her being single so they'd dressed her up to be"cuter" for the party to attract a guy.

I was that guy.

I did not care what she dressed like, but as we picked up our conversation we soon realized that we had practically

nothing in common. The outfit she had used as a sign at the party did not match her personality in any way. We finished the date cordially and proceeded on.

Signals matter.

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

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

Crafting a good description is perhaps the toughest and personal piece of enhancing your online dating profile.

There's absolutely no ideal answer, but there are definitely some incorrect answers.

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

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

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

Call to Action: A desired action you want them to take. Internet dating is inherently awkward, so help the other person by letting them know something you two can talk about. Ladies this is particularly true for you. If you do not want guys messaging you"hello" or"wanna f*ck?" Then give them some fuel to begin the conversation with.

The Headline Unfortunately, people tend to surf online dating programs the way they surf social media sites: fast and without much thought. It might be, in fact, that mobile devices have trained us to surf everything in a similar way.

Due to this, I think the headline is perhaps the most important piece of your description and you should 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: "Outdoorsy, curious, ambitious, active."

The objective of the headline is to give a fast snapshot of what's unique about you. Having a headline that's authentic, interesting, and brief 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?" It is likely that they'll laugh at the question.

As any solid content marketer knows, great content is all about respecting the medium that you're producing the content for. By way of example, if I went into a girl at a bar and said,"Outdoorsy, curious, ambitious, energetic," she'll definitely get up and leave.

The reverse is true for online dating, however.

You need your headline to be fluff free. Keep it to a 3--6 words, or a single sentence, and be certain that it is quintessentially you.

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

This is not the time to write 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 little bit of colour and possibly some talking points that you two can discuss in conversation (again, ladies, this is incredibly important to add if you would like to have more meaningful conversations).

The intro paragraph that worked best for me was: "I love being outside as much as you can! Some of my favourite things are surfing, climbing, and playing volleyball. I'm a creative at heart but I really like learning about businesses and new ideas. I'm into photography, design, 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 activities and hobbies I like 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 prevent the generic activities that could apply to pretty much anybody. I can not tell you how many profiles I've seen that list things like: "I like hanging out with friends, watching movies, binging on Netflix, and going on hikes."

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

As opposed to attempting 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 that are uniquely you.

For instance in my description above:

-- Most people like being outside and photography.

-- Some people like surfing, climbing, and volleyball.

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

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

In relationship, you basically need the individual to message you. This sounds like a no brainer, but I have found that a whole lot of people, both guys and girls, have been rejected so many times that they eventually become discouraged from making first contact.

I've heard countless stories of women who have paired with a guy who they really like, but the man never messages them. When I ask them why they don't message first, they say that they don't know what to say or they don't 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 don't want everyone to message you, so make your call to action specific.

On OkCupid they have a single section that states: "You should message me if..." ← This is OkCupid's sub-heading but you can just manually add it on other internet dating apps too.

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

The attractiveness of dating programs is that rather than having 1--5 chances to make a connection, as you would if you went to a pub for example, you have thousands of chances and"do-overs" to play with.

STEP 3 -- Making initial 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 chat online as your initial conversation is a huge limitation when you are trying to start a new relationship.

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

It makes sense then that when you take countless people and put them in an unnatural communication environment you get some pretty unnatural conversations.

While it may be fun to play around with bizarre conversation openers, if you're serious about finding a good relationship through online dating, then it's a fantastic idea to research your results a little bit.

As I got better at optimizing my profile, I started matching with more and more people. This gave me the chance to begin testing different conversation openers and see patterns that I simply wouldn't have been able to

determine if I did not have a high match rate.

Listen to The Modern Dating Show Episode 6 I'll 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.

A) "Hey! What is it going?"

B) "Hey! How was your weekend?"

C) "Question: Batman or Superman?" (or any other variation of this sort of question).

D) "Hey! How did you like X book?" (according to a book they listed in their profile) I will let you consider it for a second.

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

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

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

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

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

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

shows that you read.

If I may use the book opener to start a conversation I usually also extend it to,"Hey! How did you like x book? I am now reading'Losing my Virginity' by Richard Branson and highly recommend it!" (This is how I opened the conversation with my now-long-term girlfriend).

Pretty much every conversation I started with this opener felt a lot more natural and went past a few messages.

The next best choice,"Hey! How was your weekend?" Works nearly as well, but it's obviously confined to Sundays, Mondays, or Tuesdays. (It would be odd if you used this on a Friday).

An alternative version I tried on Thursdays or Fridays was,"Hey! This worked pretty well, but not nearly as well. I suspect it's because it sounds too much like I am 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 dialogue. Every conversation varies, but there are a few guidelines that I will put in here as hints.

First, some online dating suggestions for men: DON'T attempt to be interesting by being obnoxiously weird. I can not tell you the number of messages my female friends have shown me that noise objectively psychotic. The sad thing is that I know that the guy is just nervous and trying to think of something interesting to say. Just have a normal conversation like you would with a friend.

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

DON'T make comments about her body or appearance. Irrespective of how well intentioned you are, it'll be perceived in the wrong way. Saying things like,"you're so beautiful! You have a cute smile! You are..." will only result in a polite"thank you" and will not create meaningful conversation.

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

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

DON'T answer questions without asking any of your own. If you are tired of discussions feeling such as interviews, then be certain to ask the guy about things he is interested in also. It takes two to tango.

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

Now a proposal for both parties:

Try to move the dialogue from online to in real life relatively fast. Online dating is a great 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 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 having a date by Wednesday.

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

Step 4 -- Making a date sequence that will cause you to smile more and sweat less Once I had mastered the online part of dating, I soon realized that securing the date is only half the battle. The second half of this battle, how well goes, is largely determined before you've even set out from your residence.

As they say in real estate: location, location, location.

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

But first a question...

Where's the worst place to have a date?

As it happens, it is actually at the most commonly selected dating location: A sit-down restaurant.

Initially I was taking all of my dates to restaurants for dinner. But bear in mind, I was totally new to relationship so I was only following what I'd seen in movies.

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

What occurred next was absolutely mind blowing.

Almost like flipping a light switch, my dates enhanced tremendously.

It was not I was doing anything differently or that I had been choosing better girls 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 beverages. You continue to talking. The waiter interrupts again to your food order. You're 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 waiter comes back ten minutes later. You continue talking. Then you run out of things to discuss. What should you do next? You need to keep talking.

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

This issue is exacerbated by the fact that many 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 in-person

communication skills.

Therefore, if we are getting worse at having in-person conversations, why would you bet your entire love life on the fact you will be able to have an amazing in-person conversation with a complete stranger? I was holding on to a little ledge, about the size of a golf-ball, while the rest of my body dangled 30-feet above the floor like a giant cat toy.

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

As I let my fingers slip off the ledge I expected the sharp shock of the rope in my climbing harness. But there was no jolt. I began falling for what felt like eternity.

As it turns out, my climbing partner had let go of the rope as I had slipped off the ledge. She panicked and did not grab the rope until I had dropped 15 feet to what I was certain was my forthcoming death.

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

"Okay this date might be a little too exciting," I thought.

My entire dating profession made a 180-degree turn once I started taking my dates on fun activities rather than dinners.

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

Action -- Can we do the activity reasonably well? I've seen guys get this one pretty wrong. It's fun to teach someone something that you are passionate about, but be certain it's not too hard. Taking a girl rock climbing?

Make sure she isn't scared of heights first.

Scalability -- Can the date increase 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 earlier?

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

Now I know what you are thinking,"This man took women out to the very same areas like it was some kind of regimented assembly line?"

This was my go-to order, but, based on interests, I'd substitute different activities to keep the dates interesting.

This was merely a template which simplified my choices and decreased the cognitive load I was putting on my brain. Happy brain = Happy dates.

So here is my perfect dating arrangement: Date #1 -- Off the Grid: Off the Grid is a gathering of food trucks each Friday from the San Francisco bay.

Why I like it: One of the problems of inviting someone out to dinner is that everyone has different food

preferences. Then (if you're a guy) you've got to account for cost of food. Off the grid accomplishes this because there are over 20 different types of (affordable) cuisine. It also allows you to walk around, people watch, and get drinks. Feel like going all out? Queue the awkward white-boy dance moves.

Date #2 -- Variable: This date could change based on interests but I had a couple of go-tos, specifically: Little Italy, rock climbing, tennis, picnic on the beach.

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

Date #3 -- Cal Academy Adult Night: An adult-only night at the Cal Academy of Sciences where you can grab drinks and look at exhibits.

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 can both dress nicely for that particular night. This was also my secret evaluation because if a girl did not like science and facts it likely would not work out between us anyway. As an additional 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 just three examples of how to take online dating offline and make a reasonably successful dating sequence. Here are a few tips on what to search for on every date as you attempt to create your own dating sequence: Date #1: Look for a casual environment that isn't intimidating. Dark bars or loud places do not make for good conversation. Make certain that you can reliably visit this place, so avoid places with long waits or where you need to make reservations. Ensure you can schedule the date for a weeknight (try not to book someone's weekend for a first date).

Date #2: You've broken the ice and you've both agreed to another date, so have fun with this one! Select an activity you'll both like that isn't too tricky. Avoid intimidating activities like karaoke, group sports, or water skiing.

Ideally choose an activity which has a cadence in which you alternate between doing something and speaking.

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 confirmed you like each other, it's 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 both really are, and it should confirm whether you want to keep on seeing each other long term. Following the excitement of dates and two, there can be a lull in date 3, so be sure whatever you choose gives new intimacy to the relationship. For example, if I didn't go to the Cal Academy I'd go dancing instead.

STEP 5 -- Getting your Timing Right Perhaps among the most crucial pieces of the online dating mystery that I see guys screw up again and again is timing. Assuming the guy is the one forcing the relationship sequence (which is not always the case) there are some questions you will need to ask: When should you ask her to go on a date?

Here I will share my answers to these questions that I've found most useful. But again, depending on your context, your culture, and your comfort your answers may vary. I'll 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 think about timing, as opposed to leaving it up to"feeling."

Going from Online to Offline It is quite easy to let a great online conversation die out. You message her, she messages youback and forth, back and forth. To be able to make certain that I don't waste all my time with online conversations I found it was best to ask a woman to go on a date after about 2 days of messaging or roughly 20 minutes of constant conversation.

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

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

One thing that I discovered is that each and 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 good too. Okay how about the week after that?"

Regardless of what the prospect said, the salesperson would insist on at least"penciling" another meeting into the calendar with the option of cancelling if desired.

Once I took this technique and applied it to relationship, it led to a pretty incredible results. This rule is a bit contrarian, but it has worked really well: Always request 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.

Nobody likes uncertainty.

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

So my suggestion would be to quit playing games, both with another person and on your own. If you do not, have the respect to let them know you do not. (A gentle means to do this is by telling them that you are not prepared to date at this time. I had a woman tell me and it was the easiest let down I have ever experienced and utilized it later myself also ).

I must pause here for a single caveat: Yes, you should tell them you like them, but not constantly. Nobody likes to be smothered or chased constantly.

I see this a lot with both guys and girls who get really excited by the person they have just met and then they proceed to text them, call them, and see 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 explained,"Girls

are like shadows, the more you chase them, the longer they run away. The more you run away, the longer they chase you."

If you find someone who you want to be with really badly, don't frighten them away by being fanatical. If they like you too, 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 every single night of the week.

Permit the relationship to have some breathing room. A good way to judge whether 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 evidence for it as well.

In a number of studies, anthropologists have found that many primates invest more effort into a relationships if the people in that relationship have been forced apart. What is interesting is that researchers at the Aalto University in Finland have recently confirmed that the same is true in humans.

By data mining cell phone records and comparing telephone patterns and duration, the researchers at the university found that humans may also invest more effort into relationships if there is a probability of that relationship weakening.

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

My cadence for dating 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 -- variable This sequence meant that I would spread out the first 3 dates across a 1 month period. This allowed for enough time for the relationship to grow and helped me make sure I didn't suffocate my dates, which was particularly helpful when I was really into them.

Takeaways and Next Steps As I mentioned at the beginning of this post, these relationship approaches helped me tremendously, but depending upon your context, your culture, and your comfort, your procedure might need to be different than the one above. In fact, because relationship is such an emotional activity (similar to job hunting), it is vital to have a system in place to assist 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 hold on. Making certain you have that lap belt secured and that you have been on a few less intense rides can allow you to enjoy the ride a good deal more.

Perhaps the single most important point to bear in mind though is to let go of expectations and treat the process

like an experiment. As we often discuss about the podcast, even when you let go of expectations and just make your target just having fun with other human beings, online dating becomes something to look forward to rather than something to dread.

Like the advice of world wide investors, you want to diversify your portfolio and decrease your risk of catastrophic failure. A means of doing that is by going on dates that aren't only sit-down dinners, so that no matter how your dating partner behaves, at least you'll have a good time doing something fun.

And, to minimize the risk, you should 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 enjoy doing and then match the dates into those 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, irrespective of how well I did all the above things, I still had my share of terrible dates. The woman who used me as a meal program being just one of several. But bear in mind, once you're feeling down and enjoy giving up on love altogether: "You are not as bad as they say you are, you're also not as good as you think you are."

Take every date as an opportunity to improve yourself. If you work on your own, improving your conversations, your dates, and your connection with others, that investment will pay off far beyond online dating. Until then, strap in and enjoy the ride.

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