Chapter 8. Dating, Love, and Relationships

14 min readApr 1, 2017


Dating is an important topic because it can be so stressful, confusing, and heartbreaking. Many people struggle with their relationship goals.

This chapter contains some of the things I’ve learned and thought about dating. Dating is a huge topic. You might have great ideas based on your own experiences that are not discussed here.

My dating experience

In my life, I’ve had times when I felt very attractive and confident. During these times, it seemed easy to find an amazing girl to date.

At other times, I felt very unattractive and it seemed like there weren’t any great girls that would date me. During those times, I started looking for dating advice that could help me.

One of the differences that determined whether I felt attractive or not was my attitude and confidence. When I was feeling good about myself, it showed and I was attractive. When I was feeling bad about myself and feeling needy, I was unattractive.

When I was in a relationship, sometimes I would be a good boyfriend. Other times I probably could have been more fun, supportive, or happy. Past relationships helped me to learn and grow as a person.

The best book I’ve read about dating: Mate

I’ve read a few of books on dating. Currently, my favorite one is called Mate: Become the Man Women Want by Tucker Max and Dr. Geoffrey Miller. It’s aimed at men but women will find it helpful too. The book helps guys understand what it is like to be a woman in the modern dating scene.

It emphasizes how to create win-win scenarios so that both you and your date are happy. It gives tips on things that some guys are terrible at: being fun, empathizing with women, looking stylish, having a clean living space, developing confidence, displaying your best traits, expressing interest in someone, etc.

Mate has lots of jokes and humor. It’s funny, but the humor might make it more difficult to read if you don’t get their jokes.

Be attractive during dates by being attractive outside of dates

When I started dating, I would worry a lot about what happened during the date itself. I worried about what I said, what questions I asked, what I wore. I didn’t understand what she was judging me on or what she felt about me. I knew I had to make a good impression on the girl, but I didn’t know how. I knew I was supposed to be confident, but I didn’t know how to come off as confident.

As I got older, I learned what it meant to be confident and how to build genuine confidence. Confidence in life comes from being really happy and excited about your life. Confidence in dating comes from being able to demonstrate to others that you are a good person to be in a relationship with.

I also realized that there is a trick to being attractive during a date: the trick is to do attractive things outside of the date.

To understand what I mean, imagine I have a first date on a Saturday. How attractive and confident I am during the date is influenced by what I did during the previous week and how I felt about myself.

If I felt really good about the things I did recently then I will feel better about myself and my date will probably appreciate someone who is happy. So now, instead of worrying about what happens during a date, I focus on getting better at everything in my life outside of the date.

Why does this work? Your date is going to notice you are living a life that is fun, responsible, happy, and meaningful. These are clues to your date that you would make a great partner. I naturally gave more interesting answers to her questions because my life really was more interesting. I became naturally more confidence when I had fewer frustrations, worries, and insecurities.

Looking back on my dating experience, the times I was able to be in a happy relationship were the times when I was happiest with my life in general. I was also more confident while dating when I was spending time having fun with friends.

Neediness, non-neediness, and boundaries

Blogger and author Mark Manson is the author of Models: How to Attract Women Through Honesty. He likes to use the phrases “neediness” and “non-neediness” when writing about how to be more attractive.

A needy person needs (or wants) stuff from others in order to be happy: love, affection, attention, obedience, arguments, approval, praise, etc. Needy people sometimes try too hard to impress other people or care too much about what other people think.

A non-needy person is someone who doesn’t need anything from other people to be happy. When you’re non-needy, you’re attractive and confident. You have self-esteem rather than self-doubt. You’re naturally someone who is great to be around.

I wrote about how I could be more attractive during dates by being attractive outside of dates. I think another way of framing this is that having a great life outside of dates made me less needy during the dates.

A person who is needy will have trouble setting boundaries. A person with no boundaries will seem desperate and will not be very respectful to himself. A person with boundaries that are too strong will be too selfish and not respectful enough to others.

A non-needy person can set healthy boundaries that respects others while at the same time showing proper respect to himself.

Fix your negative traits first

You can increase your attractiveness by either improving your positive traits (adding to your strengths) and by fixing your negative traits (reducing your weaknesses). However, fixing your negative traits is more important to your overall attractiveness and should be focused on first.

Examples of negative traits that can be fixed include: having an unpleasant personality, having an unpleasant attitude, being out of shape, having poor hygiene, having a messy place to live, having bad habits, being a bad listener, being boring, being stubborn, being unhappy, having an unflattering clothing style or hair style, etc.

People can still be attracted to you even if you have some deeply negative traits. However, these negative traits might make you unattractive to the type of person you’re looking for.

When I was younger I struggled with dating because I was focusing too much on trying to add positive traits. The positive traits I wanted were to be good looking, to be popular, etc. Instead, it would’ve been much more effective to focus on fixing the thing that were unappealing about me.

Life skills are attractive

After you’ve fixed all your negative traits and bad habits you can work on developing more positive traits. “Life skills” are very attractive: cooking, cleaning, fixing things, learning, teaching, medical care, child care, conflict resolution, empathy, self-defense, etc. All of these are skills that can help you take care of yourself and your family.

Other people judge you differently than you judge yourself

Dating requires making judgements about the other person. These judgements allow each person to decide how they feel and what they think about the other person. Try to understand the judgements that the other person is making about you and why. Being able to empathize with their assessment of you can help you fix your negative traits.

There is an old saying that goes, “We judge other people based on their actions and judge ourselves based on our intentions”. For example, you might think highly of yourself because you believe yourself to have lots of potential. However, the person meeting you on a date might not be able to see that potential and will not think very highly of you.

You have to demonstrate that you can be a great partner through your words, actions, and other clues that your date can notice. Simply saying you are “nice, caring, and fun” doesn’t prove that you are any of those things. You also only have limited time to demonstrate what makes you worthy of another date. If you don’t prove you’re worth another date, you won’t get one!

Be yourself, but be the best version of yourself

“Be yourself” is an expression commonly used as dating advice. It means to stay true to your values, your desires, and your judgements. However, being yourself does NOT mean that you are currently the best version of yourself. Better dating advice is to “be the best version of yourself”. To become your best self, you have to examine your life for ways in which you could improve. Once you are the best version of yourself you’ll be much more confident.

For example, I’ve always thought of myself to be a caring, considerate person. But during my dating “career” I had to improve my ability to empathize with others.

Keep an open mind. Being your best self does NOT mean clinging to beliefs without examining them. You might examine your beliefs and find that you don’t believe in them anymore. You may also find new beliefs that help you become a better version of yourself.

Dating probably won’t make you happy if you are unhappy while single

Some people think, “I am not happy right now, but I would be happy if I had a girlfriend (or boyfriend).” However, this belief might not be true. You might have other challenges, worries, or beliefs that are the real causes of your unhappiness. If the real causes of your unhappiness go unaddressed, you will still be unhappy even when you are in a relationship.

If you’re an unhappy person, it might interfere with your ability to be a fun and caring partner. The person you date may not have the patience to help you address your problems and worries.

People treat you differently if you are confident rather than nervous

It’s amazing how differently people treat you when you are confident compared to when you are nervous.

I first starting thinking about this because I started going dancing. I go to dance events for partner dances such as swing, blues, and salsa. Between each song you have the opportunity to ask someone to dance.

I’ve noticed that when I’m confident and feeling good, everyone there is very nice and friendly to me. Additionally, most people are willing to dance with me.

But every once in awhile I’ll ask a girl to dance despite being super nervous about asking her. In this case, she will treat me very differently than if I had asked her confidently. When I’m nervous, the girl I’m talking to tends to be much less friendly and much more likely to turn down my offer to dance.

So if you want people to treat you nicely and make it easier to make friends, it helps if you can develop your confidence, or at least pretend to be confident.

Don’t be mean

Being nice on a date is really attractive. It shows that you would be a good person to date again.

I wish I had been super nice to every girl I dated. I remember one time during college there was a girl that I liked that I was mean to on purpose. I did so because I had hoped that being mean to her would make her like me more.

Not only is this manipulative, it is also didn’t work. It backfired completely and she never wanted to talk to me again. In retrospect, I realize that she already liked me a lot and was just hoping I would be nice to her.

Why did I think that being mean to a girl would make her like me more? I had some misconceptions about dating and how to be attractive. It comes from an idea that I read about online but I misinterpreted. The idea (called “negging”) claims that the most attractive women will be unimpressed by all but the most confident men, and that acting too nice meant you weren’t confident enough.

I don’t know if this is ever true or not. But it certainly didn’t make sense in my situation. Somehow I misinterpreted this idea to suggest that I had to be rude to demonstrate confidence.

Now I realize that confident guys don’t have to be mean. Now I believe that the nicer I am, the more attractive I am to the girls I meet.

Make your date feel safe, avoid being awkward

Dating has the potential to be dangerous. You and your date will both want to feel safe. Keep this in mind so you can better empathize with the people you date. Your date will be judging you on how dangerous, creepy, or awkward you seem. Some people, especially men, underestimate the importance of making your date feel safe. You might even be creepy without realizing it.

You are not the only threat to your date’s safety, either. You also want them to feel safe overall. Your date might be looking for someone that can provide safety and security in a variety of situations.


Rejection is the scariest part of dating (for many people). I remember one time I experienced a horrible rejection from a girl I tried to ask out.

Not only did she not want to go out with me, she didn’t want me to talk to her anymore. I felt horrible! I wanted her to like me or be friends me, not think I’m some kind of threat!

Luckily, one of my friends was there to console me. She reminded me that I was a wonderful and kind person, no matter what that other girl thought about me.

The other girl’s negative reaction was based on a very small information about me. The other girl didn’t know how wonderful I could be. My information about her was similarly incomplete. I don’t know anything about what she was going through or what her side of the story was.

That rejection was humiliating and painful at first. But my friend’s advice allowed me to realize that I shouldn’t beat myself up. The girl who rejected me just wasn’t the one for me. So I moved on.

Not only did I move on from wanting to go out with her, I also had to move on from trying to make amends with her. She didn’t want to talk to me again. That was frustrating at first becacuse I really wanted to say something to her. I wanted to apologize, “Sorry for creeping you out. I didn’t intend to make you uncomfortable. I want to make it right some how so you think I’m a respectful guy.”

I’m not sure if it is possible to make amends to her. Maybe the best way to make amends is to “pay it forward” by being extra respectful to other women.

It’s great if you can get to a point where rejection doesn’t hurt you. That’s where I am now. This way I can focus my energy and emotions on being happy, making friendships, and being the best version of myself that I can be.

Teaching people to be less awkward

Wouldn’t it be great if people were taught how to be less awkward or creepy? Wouldn’t it be great if people were taught how to be more confident and attractive instead?

These are difficult traits to improve because if you’re being awkward, you frequently are not given clear feedback about it. The typical response is for people to say nothing about it. In some cases, one person doesn’t realize that they are frustrating the other person.

Awkwardness can come from not empathizing enough with the person you are interacting with. The opposite also happens: you may think you are bothering someone when really they are happy to be there for you.

I’ve also met people who talk too much without listening enough.

You can ask a trusted friend to help you work on your own issues.

Dating apps

The biggest difference in dating during my lifetime has been the rise of extremely popular dating websites and smartphone apps. Examples include Tinder, Coffee Meets Bagel, OkCupid (and many more). These apps give single people a new way to discover and meet other single people.

They don’t completely replace meeting potential dates in traditional ways — I still meet a lot of single people through parties, friends of friends, local events, etc. But there are some things about it that make it convenient. For example, you can adjust the settings so that it only shows people within a specific age range or a within a certain distance.

Dating apps make it easier to meet a large variety of people to date. This reminds me of how people who live in urban areas have more options for dating than people in rural areas. Generally, people in urban areas tend to get married later than people in rural areas. I wonder if dating apps will have a similar effect and increase the age at which people get married. That would be a counterintuitive effect, since some people are hoping dating apps will help them find someone to marry sooner.

An anecdote about race and dating

I was talking with a woman from Vietnam and she told me this story that stuck with me. She dated a Chinese man for multiple years and was very much in love with him. But the Chinese man’s parents did not want their son to date a Vietnamese girl. They looked down on the Vietnamese for having darker skin and not being as wealthy. The couple broke up.

Many years later she was raising her daughters in the United States. At first she suggested to her daughters that it would be bad to date hispanic or black guys. So she encouraged the same kind of racial discrimination that she herself had been a victim of. Later, when she recognized this, she changed her opinion and told her daughters they should date whatever race they want.

Some people are feeling hopeless about dating, and venting those frustrations online

I’ve encountered people online who feel hopeless about dating. The majority of these people are men who feel unwanted and believe they will never be good enough to have a girlfriend or be happily married. They form online communities to discuss and vent with one another.

But even within these communities, there are a wide variety of opinions and ideas.

Some are trying to change themselves to get better. (That’s what I would encourage them to try to do.) Others feel they are incurably cursed with dating failure due to genetics. A few men even have extreme, dangerous, and misogynistic ideas. For example, men who express that all women are horrible or evil people.

I care a lot about helping people work through their problems. So I try to listen to and respond to people online when they are frustrated. I think it’s very noble to help someone else with their dating life.

What would I tell those men and women that are frustrated or angry? First, I would say to keep an open mind and beware of misconceptions. For example, you might feel like no one could ever love you but then later you end up in a relationship after making some changes to yourself. This happens when you don’t understand why your romantic interests reject you. Or you don’t understand how to improve yourself.

Secondly, I would say to try to find good mentors, coaches, or teachers. These people can show you what areas of your life you can work on and how to work on them effectively.

Communication and trust are incredibly important for a good relationship

The most common advice for someone with a relationship problem is, have you talked to your significant other about it?

Many times, the person HAS already tried talking to their significant other about it. And if that doesn’t work, what then?

I think that’s why couples therapy is very effective. The counselor can help make sure the discussion is fair and addresses the issues.

Trust is also very important to a relationship. If you aren’t trustworthy, or if you can’t trust your partner, your relationship is going to be very rocky.

When to End a Relationship

Relationships are a complicated topic. One common problem I see (from my own relationships, from talking to friends, reading online) is that sometimes you are not sure if you should continue a relationship or end it.

Deciding to end a relationship is a difficult choice. You wonder if the relationship is salvageable or not. You’re not sure if ending the relationship will make you happier. You also might be afraid of being single again. Some people even want to end the relationship because they think it will make their partner happier.

You have to really think about what you absolutely need from the relationship and separate it from what you want but don’t absolutely need. Trust and respect for your partner are things you need. Enjoying the exact same set of hobbies is probably a want but not a need.

Being open and honest is better in the long run. Let your partner know when you think you might not be able to satisfy one of their needs. Being dishonest might be able to keep a relationship going for a while longer, but I don’t know if it will save it.