Dating Advice That Works For You

There’s tons and tons of dating advice on the internet. A lot of it is contradictory and a lot of it won’t work for you, because it wasn’t tailored to your unique situation. Authors may project their own experiences onto other people, falsely expecting that their advice will apply. And this blog is not immune!

That’s why it’s important to only use advice that works for you, rather than blindly using advice that may backfire in your particular situation.

Let me give you some examples, some of which – I apologize – involve stereotypes:

  • Dating market effects: You have a platonic female acquaintance in her early 20s who is very physically attractive. She does nothing with her life but is constantly approached by men for her looks alone, and is very mean to them. Note, however, that it would be a bad idea for you to stay unemployed, be mean, and expect the same level of attention.
  • Employment: You have a friend who is a doctor that is highly sought after as a partner. He tells you that the solution to your dating woes is to get an MD degree, but you have no interest in medicine. Or alternatively, he attributes his dating success to the clever jokes he cracks on dates, whereas in reality, people are attracted to his social status but they absolutely hate his jokes.
  • Social skills: You feel overwhelmed in complex social situations – such as dating – due to past traumatic experiences with familial, platonic, and/or romantic relationships. You see a YouTube video of someone using a socially daring approach to getting a woman’s phone number. If you attempt to imitate this, you run the risk of crumbling in a way that will damage your self-esteem. You are better off working on your social skills.
  • Religion & beliefs: You believe in traditional family values, but you have a friend who encourages you to “just get laid”. Conversely, you are very liberal and a friend invites you to meet people to date at their very conservative church.
  • The Pick-Up Artist: You have a friend who does not respect women and goes to bars saying magic lines that manipulate women into short-term relationships. However, you are only interested in serious long-term relationships based on respect and common values.
  • Presentation: You grew up in a family that values academic achievements, but not physical appearance. You have a clearly decaying and black front tooth. You go on a date with a regular American, get rejected, and then incorrectly conclude that the problem is that you don’t have a Masters degree. In this case, you need to either make your appearance appeal to a more mainstream audience, or you have to restrict yourself to dating people who share your world view. Note: This is loosely based on a true story from my life – the person I was on a date with seemed oblivious to their decaying tooth.
  • Arranged marriage: You grew up in a culture where arranged marriages are the norm. However, your family moved to the United States recently and your parents do not have an established social network from which to select a spouse for you.
  • Luck: Your friend Marshall met his wife Lily at college. Because of pure luck, they instantly clicked, and eventually got married. Marshall has never dated anyone else in his life. Marshall tells you that you don’t need to actively date because “if it’s gonna happen, it will happen”. However, doing nothing and waiting purely for chance is not a good dating strategy.
  • Interactions with the opposite sex: You went to same-sex schools your entire life or you were home-schooled.

Some of these examples may have seemed extreme and some of them only describe single digit percentages of the American population – but those percentages describe millions of people in the United States. It is important to realize that your life experiences may be drastically different to a lot of other people. However, you can take comfort in the fact that there are probably millions of people in similar situations to you.

Life experiences are drawn from one’s family, friends, school, and/or church. These experiences result in the development of automatic thoughts and behaviors that have a profound effect in the present day. Such habits may have been perfectly functional at the time, but may be considered unusual by whichever demographic you are attempting to date now.

The question then is how to recognize which habits are helping your dating life, and which ones are holding you back. I propose 3 ways to determine this:

  • Talk to a close friend: This friend should ideally have very similar life experiences to you, be successful at dating, and can give you honest advice.
  • Talk to a counselor: Counselors have seen almost all variations in human behavior and more importantly, are objective. They may be able to tell you what you are doing wrong very quickly. If you are in college, they may offer counseling sessions to you for free. Also, by “counselor”, I mean social worker or psychologist. In contrast, a psychiatrist is not going to give you any dating advice because they are a merely a doctor that prescribes drugs.
  • Online dating: You can test your dating approach on a large sample size that should be easily obtainable through online dating. After each date, analyze carefully what went well and what didn’t go so well, adjusting accordingly. Note that unlike the first two approaches, it is very difficult to be objective and you may dismiss something you are doing wrong as “perfectly reasonable”. You can partially address this by doing reality testing – if you aren’t getting many first or second dates, you are almost certainly doing something wrong regardless of what you believe is “perfectly reasonable”.

Until next time my friends, keep dating!


How To Meet Women

Every so often I see an article or a video suggesting that single people approach strangers in everyday life to ask them out on dates – at the coffee shop, supermarket or bus stop.

There is some validity to this:

  1. You can meet someone outside your regular social circle
  2. It’s a way to practice making first impressions
  3. If you can handle a very large amount of rejection, you will eventually succeed; on the other hand, if you are very physically attractive, success might come really quickly.

Now I’ve always believed in being friendly to my neighbors and fellow citizens (in safe places). But I want to explain why it’s a terrible primary strategy for getting dates:

  1. You don’t know anything about the stranger: and they might not be even single. Chances are that they aren’t compatible and going on a date with them actually incurs an opportunity cost in terms of time and money.
  2. Your success rate relies heavily your first impressions: which puts introverts at a disadvantage
  3. You aren’t given the benefit of the doubt: because they know nothing about you – you could be a horrible stalker with aerial photos of their apartment!
  4. The success rate may be low: which can eat away at your confidence
  5. It’s frankly kind of weird: most people expect to go the coffee shop to drink coffee and to meet people they already know. This latter point is what those articles and videos are missing. You can certainly go there and start conversations with strangers, but if the purpose of your conversations is only to get a date, you basically have an ulterior motive.

Instead, I propose that your primary dating approach be to try out lots of activities. Through the shared experience of these activities, you will make acquaintances and friends. Dating will happen naturally as a side effect of meeting people and potentially their friends.

Note that it’s important to do activities that you actually enjoy in order to form genuine friendships. If you instead go in purely with the goal of getting a date, people will see through that.

Ideally, an activity should:

  1. Involve interacting with other people: You aren’t going to meet someone playing piano in your living room
  2. Have new people join every so often: This is especially important if your current social circle consists of people who only know each other and nobody else, and you aren’t intending to date any of them
  3. Be relatively mainstream: Something that appeals to a wide audience (e.g. hiking groups at is likely to attract lots of people, which gives you a bigger dating pool. It’s important to try mainstream things – including those that are a little outside of your comfort zone.
  4. Be repeated: It’s easier to get to know people you see on a regular basis
  5. Have a demographic that is amenable to making friends: An even gender balance and of a similar age is best.

If after a few weeks you find that you don’t enjoy an activity and/or that the demographic is not ideal, you should drop it and try something else. Don’t continue to do things that aren’t working out.

Note that these rules are not set in stone. For instance, if you genuinely enjoy an activity that is in a niche (e.g. volunteering at a legal clinic) and does not involve your target demographic (e.g. everyone is much older), you can still continue doing it. Eventually an acquaintance may introduce you to someone who you can date.

The main advantage of repeated activities is that you can get an accurate read of someone by interacting with them over time. You’ll learn who is single and compatible without any heartbreak or pressure. And because you have developed some familiarity, she is more likely to say yes when you ask her out.

Note that this is a long-term strategy – making genuine friendships and romantic relationships takes both randomness and time. At one activity, I met a girl instantly while at another, it took me 5 years before an acquaintance randomly introduced me to a really good future friend. So this strategy is best supplemented with online dating.

Until next time my friends, keep dating!

Speed Dating

Man: I love speed dating because I can meet lots of girls for cheap.
Woman: [laughs] Oh my god, you actually said that!

Speed dating is a fun, fresh concept that you can add to your dating toolbox. At these events, you meet 10-20 people within 5-10 years of your age and talk to each person for 5 minutes (all numbers are approximate). At the end, you nominate the people you want to see again. If there’s mutual nominations, the organizer will exchange your contact information with your matches.

There are some major advantages to speed dating:

  1. You can practice making first impressions or conversation: These are very important skills for dating. If you are nervous or don’t have much experience, the great news is that the stakes are super low since there’s lots of other people who you’ll talk to and the events are cheap. You can even prepare lines to say, in advance. In fact, I usually split the people into 2 groups and say different things to each group to test what seems to have a better effect.
  2. You can flirt with people who normally wouldn’t give you a chance: You have a captive audience for 5 minutes at a time and people tend to be polite even if they aren’t interested in you. This is very helpful if you’ve been having trouble getting an in-person date recently.
    And does the shallow side of you wonder what it’s like to be on a date (of sorts) with a stunningly attractive woman or an incredibly handsome man? Now you know (and the answer is that there’s nothing special).
  3. It’s relatively cheap: These events cost about $40. Divided by the number of people you meet, this is good value. And if you’re really stingy, these events are usually held at a bar so you could just enter the bar right after the end of the event and then approach people without paying. Obviously, no 5 minute or captive audience rule applies in this situation.

There are some drawbacks:

  1. It relies heavily on good first impressions: This disadvantages introverts and is the corollary to first advantage listed above. It can also be harder to get a follow-up date compared to online dating, especially if the rules for the event limit you to a certain number of nominations.
  2. You might not having anything in common with the people you meet: This makes it unlike meeting people through activities or online dating, and drastically reduces your chance of getting a follow-up date.
  3. These events don’t tend to be held frequently
  4. It can be overwhelming meeting so many people: You may start forgetting who is who and nominate people based purely on shallow criteria.
  5. It can be awkward: You could be stuck for 5 minutes with someone you really don’t want to talk to. Or you could end up nominating 2 people who both nominated you but also happen to be friends.
  6. Many people aren’t serious

Lastly, if you are wondering who the not-so-smooth man from the quote was, I’ll give you a hint: He writes a blog on dating for introverts 🙂

Until next time my friends, keep dating!