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 wasn't hers either. Apparently, as I discovered afterwards, I had fallen into a trap known as"the meal program." The meal program, if you're not familiar with it, is when girls 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 exact. 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 location. As I matured in my internet dating, however, I understood that this was really a response for what men do to women. Online dating sucks, but... There are three major levers in our lives that, if we pull them properly, 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 the same time. I stopped the career I had been building for over 7 years and I left my 10-year connection with my girlfriend who I thought I was going to marry. All of a sudden I was a career and relationship newcomer. I was depressed. One day, I was sitting in the shower feeling sorry for myself for over an hour. And then, for some unknown reason, my ambitious gene triggered and a little voice in my head said,"you are going to give up? No, no you are not. You're going to kick online dating's ass!" I started 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'll take you through the entire process I took to learn online dating. From optimizing your profile, A/B analyzing your descriptions, beginning meaningful conversations, as well as crafting interesting dates. We'll go over how to streamline the online dating process so that you can't only get dates, but maybe find 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 own comfort, your process might have to be different than the under. However, 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'm going to go meet fascinating people and do interesting things," you will be more likely to enjoy the process. And, if you are diligent, you might end up finding that special person.
UPDATE: As of 2019 I have been with my new girlfriend, who I met on OkCupid, for 4 decades and we've moved in together. So maybe these strategies aren't all that crazy, but maybe 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. Notice: You can also listen to the Modern Dating Show podcast, where my friend Trevor and I cover a whole lot of these strategies as we browse the current 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 that they don't define their target obviously. Deep down inside, the majority of us know whether we're searching for a serious relationship or just to have fun. The more common scenario I've discovered is that both men and women that are searching for a meaningful relationship are maximizing their dating for fun instead. I remember how one day when my coworker, Maddy, heard about my success with internet dating, she asked me to help her with her OKCupid profile. She's 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. In less than 5 seconds I saw the problem. 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 optimize for receiving dates, Maddy had chosen to only include her most provocative photos. Now I would like to be clear, there's nothing wrong with girls having"promiscuous" photos online. The problem, in the case of dating, is the arrangement of a relationship and what you contribute with. Our brains have evolved over centuries to intuitively pick up on visual clues much faster than written clues. In fact, they have found that men who are even walking with their girlfriend, will reflexively look if an attractive woman walks by activating their conscious brain. Because dating profiles conceal most information other than the profile photo until a user clicks, leading with provocative photographs sets a poor first impression. So, while it is totally fine to have hot photos up on your instagram, leading together on your online dating profile is sending signals that could be attracting the wrong type of guy. Additionally, there are plenty of classy ways to possess interesting pictures that speak to more than just the subconscious mind. Online dating pictures can be both intriguing and classy So, although Maddy was trying to find a relationship, her photographs 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 Every man who has done online dating will testify to the struggle of getting a girl to swipe right in their profile, let
alone to get them to engage in a conversation. Guys, this is completely your own fault. I have seen men 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 effect the team's chances. However, when it comes to online dating, men tend to slap a few pictures in their profile and then begin swiping like orangutans until their fingers develop calluses. Guys, stop. Before you begin creating or re-creating your dating profile, stop and think about what you are trying to achieve. Are you trying to date a lot of people? Or are you searching for a meaningful relationship? And"both" is not an answer. As the saying goes... "If you try to appeal to everybody, you will interest no one." The techniques I'll outline below work for desired outcome, but the choices you make will vastly affect your"conversion" rate. By way of instance, 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 is good to go on a great deal of dates and get practice dating (recall I was off the dating scene for 10 years), it was even more important to be sure I had been dating the right people. Fortunately I realized this before I was the victim of any more"meal programs " STEP 2 -- A/B Test your online dating profile pictures and descriptions According to a study from Princeton, it is estimated that in any relationship, whether its work or social, we make up our mind 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 image. 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's a 99% chance it is the wrong one. If one is approaching online dating as an experiment, naturally the first thing to check is your profile picture. I started this process in a very unscientific way... One hundred, and I mean 100% of these said that my first picture was not my best. It was interesting feedback, but I was not sure how I could test numerous pictures considering that I could only put one as the default option.
The response: testing across programs. I created profiles on Hinge, OKCupid, CoffeeMeetsBagel, and the dreaded Tindr. I kept my profile description the same on each profile, but I set up a different profile picture on each. I rotated the pictures across profiles before I could get a big enough sample size and be certain that the platform was not effecting results. Four of my actual dating profile pictures Sure enough, the profile picture that I thought was my best was always the one with the least matches. Interestingly enough, a picture I didn't read into, pic B, was really a huge 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 I never would have made that connection. Sometimes your photos can be your greatest blind spot. To completely test out this idea, I really enrolled a couple of friends (both men and women) to 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 easy optimization that can look to be a pain now, but it will save you from dozens, if not hundreds, of missed matches. This is the 20% of work which 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 really ask your games what they think of your own pictures. If a conversation with a game was not going well, I decided to at least get some"user comments" by asking her why she swiped right and which of my photographs she thought was best. (I also used this technique to ask recruiters why I wasn't getting jobs.) Descriptions are negotiable Now, part of this error might be my fault, because I took his advice very literally. I started to speak my mind, dress how I wanted to dress, and behave how I wanted to act. This turned out to be a horrible idea. With no filter or idea behind my actions, I rubbed more than a few people the wrong way. Now that I have matured a bit, I've come to understand that there is a difference between being your overall self and being yourself.
Whether we like to admit it or not, we are never our total selves except when we are by ourselves. Seth Godin has a wonderful podcast on"signals," that you can listen to here. In the podcast, he explains that we actively choose which signals to give to other men and women. A guy wearing a button up top, as an instance, isn't necessarily wealthy, but the button up shirt is putting out the signal that he is wealthy. Much like a person who wears all black and an anarchy necklace is signaling she does not want to follow society's rules, the man in the button up shirt is signaling that he's okay with subsequent convention. Signals matter.
In college I met a woman at a party who immediately caught my attention. I approached her and we instantly hit off. We spent the entire 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 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 round her neck. At first I didn't even recognize her, but after a few baffled blinks with my eyes I realized it was my date. She sat down and we began talking. I was that guy. 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'd used as a sign at the party did not match her personality in any way. We ended the date cordially and moved on. Choosing your signals 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 classic records, you don't want to let them know about the way you cry every time a U2 tune comes on. You need to tell them about the way you volunteer at the animal shelter, you don't want to tell them about how you ran over your cat. Crafting a fantastic description is perhaps the most difficult and personal bit of enhancing your online dating profile. There is no ideal answer, but there are some incorrect answers. The first step to getting a good dating profile description is using a clear structure.
I break down a relationship profile description into 3 parts: Headline: A short sentence someone can read quickly. Intro Paragraph: A little longer description that provides some colour to your interests and personality. Call to Action: A desirable 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 don't want guys messaging you"hey" or"wanna f*ck?" Then give them some fuel to start the conversation with. The Headline Unfortunately, people tend to surf online dating apps the way they surf social media sites: quickly 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 need to try different variations until you find one that is right 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 is authentic, interesting, and short acts like a stop sign for the individual who is scrolling through the dozens of profiles on their phone. If you ask any top-performing marketer,"how do I create content which will be successful?" Chances are they'll laugh at the question. As any good content marketer knows, terrific content is about respecting the medium that you're creating the content for. For instance, if I went into a girl in a bar and said,"Outdoorsy, curious, ambitious, energetic," she will definitely get up and leave. The reverse is true for online dating, however. You want your headline to be fluff free. Keep it to a 3--6 words, or a single sentence, and be certain 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 headline and picture being the first two. The intro paragraph gives a small amount of color and possibly some talking points that you two can discuss in conversation (again, ladies, this is extremely 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 favorite things are surfing, climbing, and playing volleyball. I am a creative at heart but I really like learning about new and businesses ideas. I am into photography, design,
and Tim Ferriss. My perfect Saturday is playing volleyball at the beach with friends. My perfect Sunday is reading a fantastic book at Promenade cafe" This paragraph outlines a couple of basic activities and hobbies I like and some non-standard things like business, design, and Tim Ferriss that might peak curiosity. The most important thing to remember about this section is to avoid the generic activities that could apply to pretty much anyone. "I like 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 those folks in your area enjoy both those things too. Rather than trying to fit in, try to stand out. Try to balance your description between things most people like, so you can discover common ground, but also things that are uniquely you. For example in my description above: -- Most people like being outdoors and photography.
-- Some people like surfing, climbing, and volleyball. -- But very few people like learning about businesses or Tim Ferriss. The Call To Action This is optional, although it certainly helps. In advertising, a call to action (CTA) is the action that you want the user to take after they have viewed your content. In dating, you essentially need 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 have heard countless stories of girls who have matched with a guy who they really enjoy, 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 do not want to seem desperate. 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 says: Again, as with this information, when in doubt just check it out. Try using a call to action and see if your conversations improve. When they don't, simply delete it. The beauty of dating apps is that rather than having 1--5 chances to make a connection, as you would if you went to a bar for example, you have thousands of opportunities and"do-overs" to play with. STEP 3 -- Making first contact and chatting The place where online dating falls flat on its face compared to"in real life" dating is when it comes to the conversation. Having to chat online as your first conversation is a massive limitation when you're trying to start a new relationship. For starters, it's a very unnatural way of communicating, since it's been proven 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 might be fun to play around with weird conversation openers, if you're serious about finding a good relationship through online dating, then it is a good idea to study 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 opportunity to start testing different conversation openers and see patterns that I simply wouldn't have been able to determine 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 thoughts I had, but in the spirit of good fun, let us test how well you can judge a fantastic opener from a bad one. How's it going?" How was your weekend?" (or some other variation of the sort of question). How did you like X book?" (according to a book they listed in their profile) I'll allow you to consider it for a second. (I'll add some distance before the answer below. Scroll once you're ready.) Scroll for the response Scroll for the answer Scroll for the answer Scroll for the response Scroll for the response Scroll for the response And the answer is...
If you guessed D, then you chose 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 some conversation starter. While I found the absolute best conversations resulting from"Hey! How did you like X book," 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 movie or a location in their pictures. The reason I suspect the book one works best though is because a) it shows you really read their profile and b) it shows that you read. If I can use the book opener to start a conversation I usually also extend it to,"Hey! How did you like x book? I am currently reading'Losing my Virginity' by Richard Branson and highly recommend it!" (This is how I opened the dialogue with my now-long-term girlfriend). Pretty much every conversation I began with this opener felt a lot more natural and moved past a few messages. The second best choice,"Hey! Works almost as well, but it's 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 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 have made contact and the other person has responded, it is time to have a dialogue. Every dialog changes, but there are a few guidelines that I'll put in here as hints. First, some online dating tips for guys: DON'T attempt to be interesting by being obnoxiously weird. I can't tell you the number of messages my female friends have shown me that sound objectively psychotic. The sad thing is I know that the guy is just nervous and trying to think of something interesting to say. Just have a regular conversation like you would with a friend. DO attempt to talk about things she's interested in but also add your own ideas. One of the most common complaints I have heard from female friends is they feel like they're being interviewed. Make sure that you ask questions, but that you also discuss things about yourself in equal measure. DON'T make comments about her appearance or body. Regardless 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're..." will only lead to a polite"thank you" and won't create meaningful conversation. Now, a couple of online dating suggestions for girls: DO be nice and help direct the conversation. Even when I have tried to be friendly and nice, I've still received quite curt or standoff-ish responses. No matter how much men pretend they don't care about the conversation, they do. And they normally don't have any clue what they're doing, so offer them some help and guide the conversation in a positive direction. DON'T answer questions without asking some of your own. If you're tired of conversations feeling such as interviews, then make sure that you ask the guy about things he's interested in as well.
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 odd, give him the benefit of the doubt and don't read too much into it, chances are he didn't either. Now a suggestion 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 is not 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. So, 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 programs, but also get them off quickly. In real life is a good deal more fun too if you know how to set up great dates... Step 4 -- Making a date sequence that will cause you to smile more and sweat less After I had mastered the online part of relationship, I soon realized that procuring the date is just half the battle. The second half of the battle, how well goes, is largely determined before you've even set out from your house. As they say in real estate: location, location, location. In which you have your date determines 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 commonly selected dating place: A sit-down restaurant. Initially I was taking all my dates to restaurants for dinner. But bear in mind, I was totally new to relationship so I was just following what I'd seen in movies. Many of them did not go well, but I wasn't sure why. After a dozen or so embarrassing (and pricey ) dates, I determined that I need to experiment with several other locations. What happened next was totally mind blowing. It was not I was doing anything differently or that I was picking better women to go on dates with, it was simply a matter of context. Here's why I believe dinner dates do not work, it goes something like this: You meet a complete stranger outside a restaurant. You have an awkward hug. You sit down at a table. You start talking, then the waiter interrupts asking about drinks. You continue to speaking. The waiter interrupts again for your food order. You're not ready to order since you have been talking. The waiter provides you"another moment." You look at the menu making comments about the choices. The waiter comes back ten minutes later. You continue talking. Then you run out of things to discuss. What do you do next? You have to keep talking. A dinner date provides no options. It's a singular task that depends on you connecting with a complete stranger
almost immediately. This problem is exacerbated by the fact that many of us are getting worse at getting in-person conversations. Spending so much time online has improved our written communication skills, but it has also atrophied our inperson communication skills. Therefore, if we are getting worse at getting in-person discussions, why would you bet your whole love life on the fact you will be able to have an remarkable in-person conversation with a complete stranger? 3 Rules for Creating Great Dates I never thought that dating 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 above the floor like a giant cat toy. "O well," I thought,"this will be a good bonding experience." As I let my fingers slip off the ledge I expected the sharp shock of the rope on my climbing harness. However, 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 just as I'd slipped off the ledge. She panicked and didn't catch the rope until I had fallen 15 feet to what I was certain was my upcoming 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 whole dating profession made a 180-degree turn once I began taking my dates on fun activities instead of dinners. Some of these activities worked better than others. But I found out that the most essential 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're walking, your scenery is shifting so you can grab new conversation topics as you go. "O look at that naked guy on rollerblades!" (It is San Francisco after all). Action -- Can we both do the action reasonably well? I've seen men get this one fairly wrong. It's fun to teach someone something that you're passionate about, but be sure it is not too hard. Taking a woman rock climbing? Make sure she is not afraid of heights first. Scalability -- Would the date grow or shrink in scale as needed? Having a terrific time? Great! No chemistry? No problem, how can we end the date sooner? Using these three criteria, I crafted a three date sequence which nearly doubled the number of successful dates I went on. I know what you're thinking,"This guy took women out to the very same places like it was some kind of regimented assembly line?" This was my go-to sequence, but, based on interests, I'd substitute different activities to keep the dates intriguing. This was simply a template that simplified my choices and reduced the cognitive load I was putting on my mind.
So here's my perfect dating arrangement: Date #1 -- Off the Grid: Off the Grid is a gathering of food trucks every Friday by the San Francisco bay. Why I like it: One of the problems of inviting someone out to dinner is that everyone has different food tastes. Then (if you're a man ) you have to account for cost of meals. Off the grid accomplishes this because there are over 20 different types of (affordable) cuisine. Additionally, it allows you to walk around, people watch, and get drinks. You can 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, specifically: Little Italy, rock climbing, tennis, picnic on the shore. Why I like it: What these actions had in common were the 3 variables: walkability, action, scalability. We could walk around Little Italy, catch cannolis, stay for drinks at Jack Karouac's favourite bar, or abort early. With both rock climbing and tennis we can alternate between activity and talking. If we did a picnic on the shore, 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 in the Cal Academy of Sciences where you can grab drinks and look at exhibits. Why I like it: This date was especially important because if a woman had made it #3, it meant I actually liked her. Additionally, it meant we might take the relationship to the bedroom. The Cal Academy Website link night fulfilled all requirements, also it was a semi-formal occasion so we can both dress well for that special night. This was also my secret test because if a girl did not like science and facts it likely wouldn't 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 all 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 arrangement. Here are a few tips on what to look for on every date as you attempt to make your own dating arrangement: Date #1: Search for a casual environment that isn't intimidating. Dark bars or loud places don't make for good conversation. Be certain that you can reliably visit this area, so avoid places with long waits or where you will need to make reservations. Make sure you are able to schedule the date for a weeknight (try not to book a person's weekend for a first date). Date #2: You have 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. Ideally choose an activity that has a cadence in which you alternate between doing something and speaking. Going on a 10 mile run is great for exercise, but it doesn't allow for conversation. Seeing a movie at a movie theater has similar limitations. 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 little 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 and two, there may be a lull in date 3, so be sure whatever you select gives new intimacy to the connection. By way of example, if I didn't 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 online dating puzzle that I see guys screw up again and again is timing. Assuming the man is the one driving the dating sequence (which is not necessarily the case) there are a few questions you will need to ask: When should you ask her to go on a date? How long should you wait between date 1 and date 2? When should you go for the kiss? 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 own comfort your answers may vary. The main thing is to actually think about timing, as opposed to leaving it up to"feeling" Going from Online to Offline It's quite easy to let a great online conversation die out. You message , she messages youback and forth, forth and back. In order to make sure that I do not waste all my time with internet conversations I found it was best to ask a girl to go on a date after about 2 days of messaging or about 20 minutes of constant conversation. Again, try not to linger at the safe-space of the digital world too long. It may feel like it's necessary, but it's very easy to waste a lot of time and momentum in the chat room. Going from Date 1 to Date 2 once I was 25, functioning as"the new man" in a tech startup, my desk was placed right behind the sales staff. Every day I overheard their sales calls where they would utilize their jedi mind tricks to close deals with multimillion dollar balances. One thing that I noticed is that each and every time they were ending a call they would ask,"okay so what does your calendar look like for next week? Busy? Okay how about the week after that? O that's no good too. Okay how about the week then?" No matter what the prospect said, the salesperson would always insist on at least"penciling" another meeting to the calendar with the option of cancelling if desired. When I took this technique and applied it to dating, it led to a pretty incredible results. This rule is somewhat contrarian, but it's worked really well: Always request the next date on the first date. One of the worst things about dating is that you are putting yourself out there. You are opening yourself up to strangers and in return you are 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. No one likes to wonder whether you like them or not. Surprisingly, most people do not mind if you do not like them, they just want to know. So my suggestion is to stop playing games, both with another person and on your own. 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 means to do this is by telling them that you aren't prepared to date at this time. I had a girl tell me this and it was the simplest let down I've ever experienced and utilized 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've just met and they then 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 explained,"Women are like shadows, the more you pursue them, the more they run away. The more you run away, the more they pursue you." If you discover someone who you want to be with really badly, don't scare them away by being fanatical. If they like you as well, there's no need to chase them. Yes, you should actively attempt to establish a date, but there is no reason to go on dates each and every night of the week. Permit the relationship to get 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 lot of truth in the saying,"absence makes the heart grow fonder," and now there's even scientific proof for it also. In several studies, anthropologists have discovered that lots of primates invest more effort into a relationships if the individuals 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 mobile phone records and comparing call patterns and duration, the researchers at the university found that people will also invest more effort into relationships if 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, paradoxically, makes the connection strengthen rather than weaken. My cadence for relationship I found worked fairly 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 arrangement meant that I would spread out the first 3 dates across a one month period. This allowed for enough time for the connection to mature and helped me make sure I did not suffocate my dates, which was particularly helpful when I was really into them. Takeaways and Next Steps As I mentioned at the beginning of the post, these dating approaches helped me tremendously, but depending on your context, your culture, and your comfort, your process might have to be different than the one above. In actuality, because relationship is such an emotional activity (like job hunting), it is imperative to have a system set
up that will help you navigate the ups and downs. By engaging in online dating you're getting on a rollercoaster of emotions and, like on an actual rollercoaster, it would be foolish to simply hop on and continue. Making sure you have that lap belt secured and that you've been on a few less extreme rides will allow you to enjoy the ride a whole lot more. As we often discuss on the podcast, 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-class investors, you need to diversify your portfolio and decrease your chance of catastrophic failure. A means of doing that is by going on dates which aren't just sit-down dinners, so that no matter how your dating partner behaves, at least you'll have a fantastic time doing something interesting. And, to decrease the risk, you need to build both an outreach and dating sequence so that you reduce the cognitive load of having to think of new dates constantly. Find a few activities you enjoy doing and then fit the dates into those activities. This is also a great way to filter out people who aren't compatible with you in the first place, which will save you time and money in the long run. Naturally, irrespective of how well I did all the above items, I had my share of terrible dates. The woman who used me as a meal plan 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, once you're feeling down and like 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 each date as an opportunity to improve yourself. If you work on yourself, improving your conversations, your dates, and your relationship with others, that investment will pay off far beyond online dating.
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