FROM THE VAULT: A Master List of Dating Advice

re-upping a fan-favorite, 01.21.2023

I’ve been traveling and away from my computer, so while I get my bearings again, I’m resurfacing one of my most popular posts of all time, from back when I wrote dating advice (remember the advice column era?). If you’re new here, this is a good intro to the kind of thing that built this audience in the first place. And if you’ve been reading for a while, enjoy this little throwback. If you enjoy posts like this and want more in your inbox (and want to support my work), consider becoming a paid subscriber. It’s cheap!

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It should go without saying I don’t always follow my own advice:

1. Yes means yes. No means no. Maybe also means no. You should never be confused. The “if he wanted to, he would” meme is real. Men do not play hard to get. This is the most important piece of advice on this list.

2. If a woman likes you, she’s automatically going to assume other women are pursuing you because she thinks everyone views you the way she does. I call these “love goggles.”

3. Many men are compulsive liars. Don’t let small white lies slip. This is a red flag, even if they come from a place of insecurity.

4. It’s a buzzword. It’s misused. But ‘lovebombing,’ even if it’s not, you know, a clinical thing, is real, it’s fun, and it’s easy to get caught up in. Don’t fall for it! It will be tempting. They’re not trying to be malicious 9 times out of 10. It’s just the tax of digital, non-stop communication.

5. Not having friends is a red flag. Shit-talking exes is a red flag.

6. You need varsity levels of patience to date addicts of any kind. Former addict counts.

7. Don’t go to their house on the first date. Cheap first dates are fine, on the other hand.

8. Convoluted dating advice for men or women is always a grift. Don’t let your romantic life become a product.

9. Be direct, not desperate.

10. He doesn’t have NPD. He wants to have sex and you’re too available.

11. On that note, you never want to be too available. Even if the person likes you. That’s how you lose your value. That doesn’t mean you can’t be a ride or die, but boundaries don’t only protect your feelings. They protect your worth.

12. People will tell you how they’ll hurt you early on. Believe them. You’re not the exception: if they did it to somebody else, they’ll eventually do it to you. This is especially true if you’re over the age of 25.

13. If you’re always pursuing emotionally unavailable people, there’s a good chance that you’re also emotionally unavailable. If you constantly feel rejected in the early stages, you can’t feel rejected “when it counts.”

14. Are they boring, or are you chemically addicted to the thrill of chasing someone?

15. Predictable is good.

16. People who let text conversations hang—i.e., don’t text you a bunch after a few hours or even days of slow responses—are a green flag. Start distancing yourself if they blow your phone up outside of emergencies or heated arguments.

17. But that said, be real: double-texting someone who really likes you isn’t going to make them stop liking you. Yeah, fifty texts will, because that’s stalker shit. But two? Three? Chill.

18. For our emotionally immature gentlemen: “All women eventually become boring, but not all women love you.”

19. There should always be forward momentum. That doesn’t mean moving too fast, but don’t let yourself fall into ‘relationship purgatory.’ Men will take the initiative if they’re serious. Sure, there are insecure men, but even they will move things along.

20. You can’t manipulate your way into a relationship with sex. If they don’t want to date you, they don’t want to date you. Doing this is a good way to get used for your body.

21. Early in the relationship: pay close attention to how they treat you when you’re down. If they minimize your feelings, you might not be a match.

22. Be a good listener. (People don’t realize how leaky they are!)

23. And on that note, never date someone who tries to argue your boundaries. Rule #1: No means no!

24. It takes three dates for the mask to drop. So always give people three dates to calibrate.

25. Because of this, wait at least five dates to have sex. This isn’t about sexual propriety; it’s just that you don’t want to miss a character flaw because there’s physical chemistry. It’s also possible that the sex is good (or interesting), but the person is boring. Not a fun realization to have.

26. Relatedly, people can only fake it for three months. That’s why a lot of break-ups happen at the 3-month mark.

27. Back to sex, sex can get better. The first time is always going to be a little bit awkward.

28. Men drop hints about the weird things they’re into through jokes. You can learn A LOT about people by what they joke about. Pay attention! (Then make them think you’re psychic by calling them on it.)

29. You should only have weird sex because you’re so into one another that you’ve run out of ways to say I love you.

30. If you’re obsessing— over someone who ghosted you, over talking to someone, over anything— it’s usually not about them. What does that person represent to you? What emotion did they make you feel? What void are you trying to fill?

31. Don’t seek someone out who’s like your ex. They’re not going to be the same. They’re not even going to be better. Heal that wound that motivates you to have a “type.”

32. It’s always better to be the less invested partner, even if it isn’t the more fun option.

33. Men confident in their masculinity (OR who have sex) typically aren’t mean-spirited about women’s appearances. Men with narrow types, unless very wealthy, have other baggage.

34. Don’t be afraid to give feedback.

35. Don’t commit to anyone before you’ve seen them handle a stressful situation.

36. Women don’t care about appearance in the same way men do. But men don’t care as much as you’d think, either.

37. Leagues are real. On the flip side, we’re pretty bad at judging who is and isn’t in our league. Geography matters here. There is such a thing as a “New York 5”!

38. “The candle that burns twice as bright burns half as long” is almost always true.

39. Intermittent reinforcement is the world’s best manipulation tactic.

40. If you have to open the notes app to type out a message, break up.

41. You might be the one who says, “Let’s break up.” That doesn’t mean you are the one who initiated the breakup.

42. Never date someone who you wouldn’t feel comfortable marrying. Definitely never date someone you wouldn’t want to be seen in a restaurant with.

43. Don’t date down to feel better about yourself. It’s not fair to them, and it’s also not fair to you.

44. Relationships shouldn’t be a sporting event to see how much suffering you can withstand. It’s not getting better. Leave while you can…

45. … because resentment becomes a festering wound.

46. Don’t date someone because it’ll “be a good story.” Novelty-seeking is a good way to go through partners like socks.

47. They’re not leaving their partner for you. And you don’t want to be with them if they do. But yes, there are exceptions. Blah blah blah limerence, but I’m a hopeless romantic who believes in life-historical compatibility and star-crossed lovers.

48. People say some bonkers shit during sex, including professions of love that they don’t necessarily mean. Don’t hang onto it too tightly. That’s not a “receipt.” That won’t be the only thing they don’t mean, by the by.

49. If they make you nervous beyond the initial “do they like me?” phase, that’s not a good thing. That easily identifiable physical feeling of anxiety may subside with time, but it’ll be channeled elsewhere and break you.

50. Likewise with jealousy. You might have jealousy issues, but it’s a flag if you feel uncharacteristically jealous (e.g., feel like you need to audit their social media footprint). (Stop auditing his likes.) (He’s never going to stop liking other women’s selfies.)

51. But we all feel jealous sometimes. You’re over them when you stop feeling jealous. (I repeat: stop looking at their social media profiles from an incognito tab! Close it right now! Yes, he thinks she’s hot and that’s none of your business!)

52. There’s a secular and wholly apolitical reason that body count matters: you start to get jaded after a while. Being “spiritually ran through” is a thing.

53. The most durable relationships are between people who grew up with similar values.

54. If he texts you six months later and says he was “actually in love with you,” he’s horny. If she texts you six months later and says that she was “actually in love with you,” she feels ugly.

55. Beware the woman who wants to use you as supporting infrastructure for her self-esteem. Incels are right about “emotional tampons.” Are you friends, or are you a reliable source of male validation?

56. It’s not that they need to be texting you all the time, but a change in texting rate can be a bad sign. I’m sorry. You’re not going crazy.

57. Hope is the last thing that dies. And it takes a long fucking time. Years, depending. Buckle up.

58. You should like how they smell. No, really, that’s extremely important.

59. If you have to drink or smoke to have sex with them, you don’t like having sex with them.

60. Aspire to reach a point where your conversations are unintelligible to third parties because you’ve developed your own couple-language.

61. Please don’t get married after dating for six months. Or three days. Or any similarly bananas-short length of time. And for most people, let’s tack on under the age of 23. I don’t care what your alternative histories or statistics say. We don’t live in a world that’s equipped us for it. You will most likely get a divorce. In the U.S., you’re lucky if you’re a fully formed person at 25. Of course, there are exceptions to this, and you might be one. But the people who promote otherwise DO NOT HAVE THE LIFE EXPERIENCE TO BE GIVING THIS ADVICE.

62. For the people who need to read #61: Do you want to be “based,” or do you want to be happy?

63. Are you “into being dommed” or do you crave abuse?

64. “Women [who love you] won’t just accept your flaws. They’ll do mental acrobatics to love them.” Women: this one is for you.

65. If you don’t hear from him for a while, remember “I’m busy” or “I’m depressed” are both empty excuses. I know that sounds callous, but it’s true. It’s true that men say this when they lose interest but aren’t ready to cut it off completely.

66. And on that note, “Don’t let yourself be disrespected by someone you lowered your standards for.” and “Remember when you had to convince yourself s/he wasn’t ugly.” are worth remembering.

67. They’re not misfits because the world is wrong. They’re misfits because they are wrong. Sorry! (19-year-old women, this one’s for you.)

68. Do they only say “I love you” when they’re horny, or do they say it whenever? [thinking emoji]

69. Just because something ended doesn’t mean it wasn’t important or meaningful.

70. If none of this advice feels right to you, just find someone you’d create great art for. A film. An entire Twitter personality. A book. Inshallah you two get married.

71. When people give advice, they’re speaking to themselves as much as they’re speaking to you. That doesn’t mean their advice is bad, but it’s important context.