Dating / Courtship / Flirting (Self-Improvement)

Table of contents

Child pages


  • My understanding is that in the old days, people would learn to flirt by watching / interacting with older siblings / friends (even if just a few years older).
  • Nowadays society is very segregated by age, and there isn't a lot of interaction with older or younger groups.
  • Thus, I never learned to flirt from anyone.
  • Thus, I am not good at it.


  • It's unfortunate how little guidance people are given on this subject nowadays.
  • get that clip from Amarcord
  • write about The Good Earth, it has some interesting observations on male-female relationships 

Dating sites / apps

A note I wrote down: 

Something that works very well for me when using OKC and Tinder to practice conversation skills was to use the red tomato timer to force myself to limit the practice to 25 minutes. I also found this helpful with CrossFit, where they put the timer on the board and that prompts people to use more intensity when practicing. Previously I would spend too much time thinking about what to say, which is a bad habit.
  • Asking women right off the bat if they want to go to lunch or dinner seems to be like asking a bank for a big loan without any credit history. You need to get the bank comfortable by taking small loans first. Another analogy is getting a train moving: the conductor rocks the train back and forth until he can break the train's inertia. That seems to be why women want to trade messages first.

Initiating a conversation

  • Consider making short joke-y comments / observations
    • 2015.05 - I was talking to a perfume salesman and two women walked by, each texting someone on their cellphone. He said to one of them something like, "You don't have to text each other, you can just talk to each other!", and at first the woman didn't realize he was talking to her, then she looked up and said something like, "What?", and he repeated himself, and she laughed. After they walked away he told me that he had a whole bank of short phrases he can shoot out to people as a way of trying to start a conversation. 

Being smooth

  • I'd heard about "being smooth" for many years but it wasn't until I actually started trying to get women to go on dates that I realized just how important it is.
  • The key to being smooth seems to be having a very good ability to gauge how a person is likely to react to your behavior. For example, what will they think / say if you ask them to do X? Will they agree?
  • From what I can tell, to gauge how a person is likely to react you need to keep a mental history of how they've reacted to other things in the past, and how they're reacting to things you're doing right now. You want to send out a probing-request that tells you the information you need without risking disaster. For example, before asking a woman to marry you (a high-risk behavior on your part), you could ask her what she thinks about marriage (a lower-risk behavior on your part).
  • I remember when I was going to swing-dancing classes I often thought about smoothness when leading a dance. Many men, when they're inexperienced, will unknowingly try to lead a woman to do something she's unable or doesn't want to do. So dancing may be one way to practice.
  • I should figure out how to categorize requests.
    • I think a big factor is how much time you're asking from the other person. Going to dinner will require several hours of the other person's time. Responding to one of your messages may only take a few minutes. So trading messages for a while (until the word count or message count has hit a certain number?) may be the best bet. Your goal should be to demonstrate value (ie convince her you're worth her time). I should figure out how to categorize the different ways in which a person can demonstrate value.

Billy Joel on Not Working and Not Giving Up Drinking

A.G.: Right before you married Christie Brinkley, you dated Elle Macpherson. And later you married Katie Lee, also a young, very beautiful woman. Do you think your relationship with female beauty is any different from any other red-blooded American male?

B.J.: A lot of guys are just too intimidated to even ask them out, but I had a great way to meet people. People are just interested in you because you’re a rock star. O.K. Some guys use a car. Some guys have a cute dog. I’m a rock star. That’s who I am, what I do. What’s wrong with that? 

Misc articles: ... ating.html


In other times / places

Making Conversation

  • Ask a question and make a comment at the same time, or make various comments on different things in rapid succession, or ask several questions at once, as a way of giving the person a lot to potentially respond to. They can choose to respond to the question or choose to comment on your comment.
  • I often feel nervous about trying to start talking to people because I don't want to bother them. My father would yell at me for interrupting him and so I don't like interrupting anyone. I also don't like being interrupted myself when I'm doing something. I think the key is to learn when it is ok to try to talk to someone and when it isn't a good idea. It seems to me that what you open the 
  • You need to practice getting up and walking after someone who has walked by. Even if it takes you 30 minutes to calm down and get yourself out of your seat, you need to do it.
  • At least in the US: don't keep staring at people after they've made eye contact. If they look at you look away like you're embarrassed. It's less intimidating to the other person.
  • Practice: ask people to watch your stuff while you go to the bathroom. Don't depend on them doing it, though. Have your laptop locked up, take your phone with you, etc.

OKCupid / Tinder / Online Dating Sites

  • the goal is not to get a date. the goal is to get comfortable making small talk, so that when you see a woman in public, you'll feel comfortable striking up a conversation.
  • rate yourself by how quickly you are able to get a response out (assuming the response is of reasonable quality). If you're spending 5-10 minutes thinking of something to say, that's bad.
  • the key to good small talk is to try to throw out as many possible conversation topics as possible, so that the woman will more likely hear something she's interested in talking about. A good way to do this is to make a short observation (eg relate a short story) and then to ask a question.
  • Swipe right on anyone who seems to be putting in effort into grooming themselves, even if you aren't attracted to them.
  • Interesting discussion re: a guy who wasn't able to get people to meet in-person

General observations

  • I would say one downside of being too nice is that the other person may think they don't have to work as hard for your affection, and so they may end up doing more things that annoy you, simply because they aren't attending as much to their behavior. I've seen myself behave this way (I'm not happy about it) when women were very nice to me. And I've seen women behave this way when I was very nice to them.

Where to meet people

  • From what I've read:
    • libraries
    • grocery stores
    • the gym
    • college campuses - It occurred to me while seeing a group of soldiers that there is probably less competition for the attention of college women than would exist if all age groups were interacting with each other constantly, because a lot of young men are forced away from campuses. For example, a lot of young men go into the military.

Misc Advice

Dad's advice

  • Paraphrasing: "The problem with dating someone who isn't similar to you is that you're never in agreement with your partner about how to spend your time."

Adam Lyon's advice

2010.02.12 - SFGate - Boot camp teaches bachelors how to score booty ... 273359.php 

  • speak to women at eye level (huh?)
  • be liberal with the compliments
  • subscribe to Cosmopolitan
  1. Make dating fun (don't do dinner and a movie, do something more original)
  2. Ask more than one woman out: "I'd stagger three dates throughout the afternoon to evening"
  3. Text the woman in the morning before the date telling her you're going to be five minutes late as your day is really busy and ask if that's OK: "This may sound ridiculous but it will give her the opportunity to cancel if she's on the fence about coming out and stop you getting stood up waiting for someone who isn't going to show."
  4. Treat her like your girlfriend on the date: "Don't do the awkward thing of shuffling your feet and wondering if you should or shouldn't hug her. Give her a big hug, a kiss on the cheek and then link arms. Start a date like this and add in a few simple acts of chivalry like opening doors and pulling her chair in at the table for her and you're on to a winner."
  5. Multiple venues are better than one: "If you want to bring her home or get back to hers, she needs to be used to being with you in multiple locations. If you go to a coffee shop, the aquarium, bowling and an ice cream shop all in one night, she's going to be much more likely to agree to heading back to yours to finish the night off."

 Sara's advice

  • Sara is one of the most-experienced daters I've ever met. She would definitely be described as a "player" and "a natural".
  • have a conversation with her until you find something you two have in common and then switch numbers, ask if she has fb and friend her. have a relationship by messaging for a little bit considering the distance between the two of you and then next time you're in town ask her out to breakfast or lunch on the weekend, maybe a date to the library something innocent and then take it from there. i think movies or dinner might be too serious at first

J: I don't like "You should let me," it sounds like an order. What about "I'd like to"?

S: "You should let me" sounds more confident. "I'd like to" sounds a little desperate and dopey.

L: I don't know, I think "You should let me" sounds manly. Young girls want to get scooped up and wisked away.


Q: I shouldn't contact mutual acquaintances?

S: It might be creepy if you contact them, a little stalker-like.
J: ...but maybe also get together with mutual acquaintances to catch up so she can hear third hand what a cool guy you are. and DON'T bring up the chick's name unless they do first

L: Yes, good idea, just don't inquire with her friends about her!

  • Q: Why would a woman contact a guy and then stop responding without an explanation? And do that multiple times? (I went into more details)
    A: Sounds to me like she likes the attention. She's probably mad at a guy and is trying to make herself feel good.
    Hmmm. Very strange. I would say to her straight up that if she doesn't want you to contact her to tell you. Girls like honesty more than anything! Be very straight with her, ask direct questions. I would even go to the point of saying: You reached out to me and then when I respond you ignore me. What's up with this?
    You'll never understand women no matter how much you want to. We don't even understand ourselves! We do things spur of the moment that feel good and then feel completely differently the next day. We love honesty and attention, yet too much attention pushes us away and we get angry at the truth. We are nearly impossible to please and the grass is ALWAYS greener on the other side.
    I would absolutely say it's for attention. If you've slept with her there might be a possibility she is interested, but not enough to commit. If she's just saying things and not acting on them then it's for the attention.

    Q: I read online that when a woman starts getting really explicit out of nowhere it can be a test, and if the guy gets too excited he fails. Does that makes sense to you / have you seen that?
    A: Too nice, or acting too interested will totally push someone away. It could be a test, but that doesn't take away from the fact she sounds crazy. Playing hard to get will always make them more interested, but not too hard. That will piss them off.

Lauren's advice

  • To be perfectly honest The whole process of dating is supposed to be a surprise. I would not explain yourself quite yet. Girls love mystery. Simply ask her to something non threatening like coffee or lunch which might be better because you can hold her attention longer through lunch. Then you find out about HER. Dont pry but ask her the basics. Girls love to talk and believe someone is that curious about them. If you see and talk to her regularly then most definitely just ask her what her favorite food is and ask her when she is available to let you treat sometime!

    You need to walk in there WITH CONFIDENCE! Ask this girl to lunch and if she says no big deal move on to the next! You have nothing to lose, and they only have something to gain by being with you. Women are naturally drawn to confident yet humble men, i am anyways, be yourself but stop trying to master the art of meeting a girl and just dive in head first. The only way your going to get good at this is by practice so stop wasting time thinking about it and just act on instinct. The more you analyze this the worse your going to do! Women dont want to be analyzed!

Misc advice ... UuwDPlViko