Some Things I Have Learned in a Couple Decades of Occasional Dates, Relationships and Sexual Encounters

60 of them, actually. They are all, of course, very arguable.

  1. There are many times when planning a first date with someone feels exciting and like a great idea at the time, but when the actual day arrives, you find yourself wanting to cancel said date because you don’t really feel like going and meeting a person in-real-life for the first time after a long day of work or just trying to live, and you reason that if you were to cancel, you’d probably go through the rest of the day with a lower level of angst than you’re currently experiencing—which is often very appealing and comforting.
  2. Condoms feel and smell terrible (adding another scent to the already semi-strange sex funk) and definitely take away from sexual sensation, but they’re also great for many obvious reasons. A less-obvious one is that after having sex with one and checking to ensure it didn’t rip during the act, you’ll be able to move on with your life sans semi-frequent panic attacks where you think you may have accidentally impregnated a woman or contracted a chronic STD. It’s important to try and keep this in mind in the moment, because a month or so of worry more than negates the brief better feeling of skin-on-skin fucking. Sex is still sex, even if you rock a rubber, you know.
  3. If you don’t feel like going on a date, then don’t go on that date. There are too many things in life we have to do that we don’t really feel like doing, and dating isn’t one of them. If you’re not excited to go out with someone, just don’t do it. There’s really nothing wrong with going home at the end of the workday and drinking boxed wine on your couch while you watch Netflix (unless you’re one of those people who views drinking alone and/or the concept of boxed wine as “something wrong”). I mean, what are the odds this person is going to be “The One” anyway? Pretty slim, probably.
  4. As statistically improbable as it is, anyone you go out with might be “The One.” There’s really no way of knowing.
  5. There might not be such thing as “The One.”
  6. If you’re nervous and a little bit anxious to go out with someone, especially for the first time, it means you care at least a little bit, and if you care even a minuscule amount and end up canceling the date, you might always wonder what might have happened. So always keep that in mind before you decide to cancel the date to go home and drink boxed wine and watch Netflix.
  7. Sometimes being decisive about dating-related things is very difficult.
  8. It’s very possible and maybe even likely that I will die alone.
  9. Don’t let yourself wonder too much about what might have happened or what might have been — especially when you find yourself in a position where you can’t do anything to change your present situation. It’s important to learn from your past, but it’s better to not dwell on it. I mean, yeah, she’s still stunningly beautiful. Yeah, she’s happily married. Yeah, she has a beautiful baby boy. No, she doesn’t think about you much at all anymore. She’s moved the fuck on, and the best you can do is try and do the same. The only shot you’d ever have is if she ended up single again.
  10. When you are looking back on past relationships, remember to look at it as a whole. The worst thing you can do is lament only the good parts and edit out the sad or downright nasty parts. You might miss certain things about someone, but if it didn’t work out there are likely things you don’t miss, too. And if you really, truly miss everything, that sucks, but you’re going to have to move on at some point anyway.
  11. Actually, you never really have to move on, but you should try, because a life spent lamenting someone from your past isn’t much of a life at all. Longing for someone for years doesn’t usually work out the way it does in The Notebook.
  12. Every moment you’re thinking about someone else, thinking about what could have been, is another moment when you could be maybe finding the right person for you. And chances are you’re supplementing this thinking by checking out their profiles on various social media outlets (if you’ve still got access to said profiles). If that’s the case, remember that most people only post the best of their lives online, so you’re getting a skewed version. I bet they go through severe bouts of extreme existential misery just like you and me!
  13. There will be times in your life when you hope for someone to break up with their significant other. This includes divorce. You will not consider (at least not for very long) how emotionally devastating it will be for the person you want to become single.
  14. Sometimes you will have your shot. Sometimes you will blow it. Sometimes you will never get your shot. Both scenarios are terrible. The former is worse, probably. With the latter, at least you can blame “fate,” whatever the fuck that is.
  15. “Fate” probably isn’t real, and it’s highly unlikely that everything happens for a reason — that chance without any particular meaning (especially predestined) is a crucial component to so many facets of our lives. Sometimes I find myself wishing the opposite were true, but deep down I know relying on fate or things happening for some pre-determined reason is just a cop out for when people don’t want to really go deep and examine why something did or didn’t happen to or for them. One time I broke up with a woman and my friend told me everything happens for a reason and I said, “Yes, that reason is that she is awful and was very mean to me on many occasions,” which was a reason, but I think very far from the sentiment she was attempting to deliver.
  16. Many people say that luck isn’t a real thing, but I think it’s more plausible than fate, as a concept. Fate implies that the decisions and moves you make help put you into a position where things are going to happen that have already been semi-pre-ordained as long as you make it to whatever position is in question — and that some entity or entities has gone out of its way to care enough about you to put those locations, etc. in order. Luck just implies that you were randomly in the right place at the right time. Which is the same as chance.
  17. Self-diagnosing something you believe might be an STD is not a great idea. That’s how you end up thinking a nickel allergy is herpes, or that a simple case of eczema is a fucking systemic yeast infection.
  18. Premature ejaculation is extremely embarrassing and leaves women unfulfilled at best, but I suppose it can also be seen as a compliment. Though in my (rather vast) experience with it, it’s not generally seen as the latter.
  19. While the two can definitely influence and feed off of one another, there is a very, very, very big difference between relationship anxiety and depression and real clinical anxiety and depression. If the former has been the only form of both you’ve experienced to date, then I really, really, really hope you never have to feel the latter. I’ve spent a lot of time listening to Bright Eyes, and it wasn’t until I was a little bit older that I really felt empathy with Conor Oberst’s sad words. This empathy is often something I wish I’d never felt—that it hadn’t chosen, seemingly at random, to make its way to my surface thoughts and emotions. (Serotonin is weird, man.) Before that happened I’d been using his words as a surrogate for my own melodrama.
  20. Sometimes sleeping over can be a more intimate thing than boning. Especially if you refer to the act of sex as “boning.”
  21. An awkward morning is not always better than a lonely night. A lonely night is just one lonely night. An awkward morning can have lasting implications. Though both do build character in their own ways.
  22. “Having Sex” and “Making Love” are two very different things. Also, the term “Making Love” doesn’t make any fucking sense. Think about it. You can’t make love. It’s not something you manufacture. Though sometimes I wish it was. (But if you could manufacture love, it would lose pretty much all of its luster.)
  23. People you date will try to change you — even if they promise you they never will, and even if they don’t necessarily know they’re trying to. Sometimes these changes are for the better. (Like if she helps change your habit of always being late for everything.) Sometimes they aren’t. (Like if she tries to change your style by gifting you an Ed Hardy T-shirt and Diesel watch, to replace your plain pocket T-shirts and calculator watch, respectively.) In any case, make sure what you’re changing isn’t something that’s going to compromise who you are. It’s important to stay true to yourself, and besides — why would you want to date someone who doesn’t like who you are to the point that they actively try to make you into a different person?
  24. It generally takes people three or so months of dating before they really start to reveal who they are. That’s about how long you can keep your shit semi-bottled up and kept secret from a person you’re intimate with and spending a lot of time around.
  25. Some people end up with better looks and better fortune than you. It happens. There’s no use dwelling on it, because that won’t change shit. Unless you’re one of those people who gets angry about his or her lot in life and/or about rejection, and you use that anger to change your position for the better.
  26. Everyone is superficial to some extent. It is, of course, what’s on the inside that counts, but the outside counts too — and anyone who says it doesn’t is lying to you and/or themselves. What’s inside doesn’t usually get someone to swipe right on you or approach you in a bar. Sexual attraction is a huge part of any relationship, and there’s no shame in admitting or accepting that.
  27. When you’re early on in the wooing/courting/dating process, the worst thing you can generally do is to follow your instincts. If you’ve had a great date and want to talk with that person more and see them again soon, you’re going to want to send them a text message or give them a call probably almost immediately, and it’ll seem like the right thing to do, this whole “showing interest” thing. But it’s not, a lot of the time. People tend to freak out when someone is honest about the fact that they actually, you know, want them and enjoy their company. You should usually go opposite your instincts and act aloof or whatever. You’re not supposed to answer texts immediately even though technology has made it much easier than ever before to do so. You should not always be available. Because people want what they think they cannot have, and they don’t want what comes easily to them. This all seems shitty and it is, because it’s wildly unfortunate that you have to play games or actively try to mess with the head of someone you’re falling in like with. But just because something is shitty doesn’t mean it’s less true.
  28. Maybe the thing to do is to just be yourself all the time and do and say what you think and what you feel, because that just might be the best way to meet the person you are perfect for. (I can’t vouch for this but I’m hoping one day I can.)
  29. There are “relationship people” — the ones who either seem to be extremely lucky and keep meeting great matches not long after a break-up, are incapable of making their way through even a short amount of life alone or both. The people who never seem to sleep alone, who jump from one person to the next and seem happy about it. (Occasionally, these are the people who you bide your time waiting for them to break up with someone so you can finally let loose with your feelings, but then they end up with someone else before you can even make a move.) And then there are people like me, who either have extreme intimacy and commitment issues, or value the idea of a serious relationships so highly that they’re hesitant (maybe to a fault) to enter something that might become one. Both sides of the spectrum tend to judge one another on some days, and admire one another on others, depending on how things are going on their respective side of the commitment divide.
  30. There are worse things than being alone. Like the time of night when no decent dumpling delivery places are still open. Or settling. Those are just two examples.
  31. By the time I get married (if I ever do) it’s likely that every decent wedding hashtag will already have been used in triplicate.
  32. Ejaculating on a woman’s face is overrated.
  33. My hormones are strangely influential and controlling, to a point it simultaneously perplexes me and pisses me off. Like, I know Bristol Palin is a horrible human being, probably irredeemably so (I know she was brainwashed by her parents, but come on — you’ve got to think for yourself at some point), but if she showed up at my apartment right now and was like “Hey, wanna fuck?” I’d almost definitely give her a shot at the title. The dick wants what the dick wants, and sometimes it takes the lead while the heart shrugs and is like, “I don’t know; guess I’ll let it have this one and then regret it for years to come.”
  34. I don’t think you necessarily have to accept someone ghosting on you. It can be fun to continue messaging them as if you have no inclination whatsoever that they’re ghosting on you, until they either respond and say they don’t want to go out with you again, or they block you.
  35. If your ex (who became one of your best friends) stops talking to you because her current boyfriend doesn’t want her to interact with you anymore, an immature but very satisfying thing to do is to poke her boyfriend on Facebook every few months or so, just to remind him that you’ve still got her V-card. And that she cheated on her previous boyfriend with you (though it’s doubtful she’s told him that, so you might want to send it in a direct message at some point).
  36. Sometimes, getting drunk and poking a stranger on Facebook because your also drunk roommate dares you to can actually lead to one of the more significant relationships of your life.
  37. Sometimes a woman will choose a gigantic douchebag over you. Other times she will choose an actually likable guy over you. The former is much easier to deal with than the latter.
  38. Ponderosa is not a great place to take a girl on a date pretty much ever. It’s especially not a great place to take a girl on Valentine’s Day.
  39. The venue for a date often means less than you think it will, though with some people the venue is everything. You probably don’t want to date the people who think the venue is everything. It should be more about the company. (Unless the venue is a Ponderosa.)
  40. For whatever reason, the better in shape you are, the more women seem to want to fuck you. And if you don’t take care of yourself physically, it’s (obviously) not fair to expect a woman who does to take you seriously as a potential suitor. Sitcoms are very misleading about this paradigm.
  41. There’s a strange moment after you orgasm that is pretty much the only time ever that you’re like, “Oh, I could live without sex. It’s not that big a deal.” That moment doesn’t least very long.
  42. Home-wrecking is strange, because sometimes a person will cheat on their significant other with you, and then opt to keep on living their lives as if nothing has happened. And oftentimes their significant other never even finds out about it. But then there are other times when, eventually, they leave their significant other and want to start a relationship with you, but how do you know that they won’t cheat on you at some point, if they were so ready and willing to cheat on someone else with you?
  43. You shouldn’t cheat. If you find yourself falling for someone else or sexually attracted to them to a point that you might want to act on it, just press pause and break up with your significant other first. People fall out of love and into love with other people all the time. It happens, and there’s not really much you can do about it most of the time, and it’s better to follow that than to stay in a relationship with someone else just out of some sense of moral obligation, but you become a real fucking asshole if you cheat. You may think that you should explore things with another person before breaking up with your significant other or partner, but if you’re thinking that, you’re using your current relationship as a safety net, and that’s pretty reprehensible.
  44. When your friends weigh in on your relationship or someone you’re dating, you should listen to them. you don’t have to agree with them or take any action based on what they say, but it’s extremely valuable to have input from people who love you and who have known you for a very long time.
  45. You should never call a woman crazy, because it’s way too general and used way too often when not warranted. If you want to call someone out for something negative, make sure you have enough to go on to actually articulate the issue you have with them.
  46. Keep a clean apartment. Shave your pubes. Keep condoms handy. Be ready to pull out. Be prepared, always. When you walk out your door, you can never know for sure exactly what’s going to happen. Or what won’t.
  47. Objectivity is wildly valuable when it comes to dating and love. If things don’t work out or you’re having an argument or something, being able to look at it from a non-partial point of view (the best you can) will help you. I spent years moping around like a bunch of girls had wronged me, when in reality I was the asshole the entire time. You learn nothing and improve nothing if you alway stay firmly rooted on your own side of things.
  48. There are different styles of kissing, and you might find that your kissing style meshes extremely well with someone else’s. Just like sex as a whole. If someone’s approach doesn’t fit with yours, it might not be that either of you is doing anything wrong, only that you’re just not great at kissing each other. (Styles can change.) But then there are also people who are just quite frankly awful at kissing, and it’s kind of baffling to try and figure out where they learned their technique.
  49. Don’t go down on a woman just because you want her to go down on you after. It’s not an obligatory thing. Do it because it (theoretically, if you’re doing a proper job) makes her feel good.
  50. The most exciting thing about sex is the opportunity to make someone else feel good. It’s not about you getting off. You can get yourself off anytime, and if you’re anything like me you probably have been at least once a day pretty much every day since you first discovered you could pull yourself off. Even if you’re too drunk or whatever to get off yourself, you should always strive to get your sexual partner off. You can whack off to the memory later. The Spank Bank is a beautiful thing.
  51. It’s more than fine and rather normal to want a relationship. But it’s not something you should ever force. A relationship isn’t something that should be viewed as a goal or something you want to achieve, because that kind of mindset leads to settling, which ultimately leads to either divorce or people gutting it out even though they both know they aren’t right for each other. (Oftentimes, children are involved.) I spent a few years of my life trying to force myself into relationships with women who I knew deep down were not right for me, or even close to it. It took my friends’ semi-harsh but accurate input to make me realize this. I was settling because I had this strange goal of being in a relationship. It didn’t work out for me and it doesn’t work out for most people who aren’t beautiful women who are actively seeking out a partner who is wealthy.
  52. Dating can be very costly and something you have to budget for. I (happily) can’t quantify the number of bourbons I’ve purchased for women I’d never speak to again. If I could, I’d probably just never go out on another date again, and spend all my whiskey money on myself.
  53. Porn is not good for dating or love, but it’s not something that’s going to go away, and it’s not something that most people are going to abstain from, because it’s so easy to access and enjoy. What it does, I think, is create the illusion among some that they can carnally interact with different people on a daily basis, and that’s not true for most of us. It can be true for the extremely rich and beautiful, or for an average or better-than-average-looking woman (if she really wants to), but these aren’t the people who generally get addicted to porn.
  54. It’s weird when you see someone in a porn video who looks a lot like someone you know or used to date. It’s even weirder when you come to this realization and become even more aroused because of it.
  55. Monogamy might be crazy and unnatural. Sometimes I think it is. Sometimes I think otherwise. If you feel that way it’s fine, and I hope you get to fuck a bunch of people at different times throughout your life, but it’s like most beliefs or religions in that you shouldn’t spend your energy trying to convert other people into a life of open relationships and orgies. Some people are genuinely interested in only fucking one person for the rest of their life, and in building a life with that person. There’s really nothing wrong with that.
  56. Love isn’t definable, really, because it means different things to different people. And you can think you’re in love when you’re not, or that someone is in love with you when they’re not. (Love is like orgasms in that way. I thought I gave an ex one one time, but I hadn’t. She thought I loved her, but I never did. We were both under the incorrect assumption for years before the air got properly cleared.)
  57. Depression can mess with your sex drive in negative ways, but you can also become more depressed when you realize you’ve gone nine months without sex and that this is largely because your depression has influenced your decision (whether voluntary or not) to not go out there and try to allow yourself to be intimate with someone.
  58. There’s no shame in going a while without sex.
  59. It’s always their loss. If not right now, make sure that someday it is. Or move on and live a happy life where you’re not constantly seeking vengeance. Either way.
  60. If I don’t get laid soon I’m going to lose my fucking mind.