The Bitter Bitch's Guide

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Assholes & Idiots

10 Things I’ve Learned Over 20 Years of Dating

As a 40 year old woman, I’d say I’ve spent about half of my life dating. In one way or the other, I’ve spent the last 20 years with an asshole, thinking about an asshole, obsessing over an asshole, changing myself for an asshole, or pining away for one. Does that make me an idiot? Well, yes, but it also makes me human and unfortunately, when it comes to love and the affairs of the heart, there’s really no smart way to go about it. After my most most recent entanglements, I couldn’t help but notice the similarities between past affairs and it made me realize some things never change and after taking this sideshow on the road, I feel like I have an even better handle on this thing we call love. Therefore, without further ado, here are my top ten evergreen lessons for dating assholes and idiots.

I remember when I was younger and I couldn’t wait to grow up and meet someone I didn’t have to play these games with because, surely, men in their 30’s and 40’s don’t play silly kid games, like ignoring you, stringing you along, or ghosting you. Certainly a grown man, cultured and refined, has learned communication and transparency. Certainly as women evolve so must men, right?!

Bahahahahahahahahahahahahahahahaha. No.

The truth is it never gets easier. Just the opposite - it gets harder! Take that immature teenager who just wants to fuck everything and add decades of disappointment, fear, and trauma and now you have an entire dating scene full of extremely maladjusted people who’d rather be alone than waste one more ounce of effort coupled with a bunch of geriatric fuckboys who never grew up. It’s a fucking mess.

Yes, for many people, the pressure of finding someone well into adulthood begins to make dating seem like a daunting task. With the invention of online apps, there doesn’t seem to be any real connection anymore, but it doesn’t have to be the worst thing you’ve ever done if you look at it for what it is. I’ve found after dozens of horrific dates, changing my expectations helped change my view on it. Stop putting so much effort into getting to know them virtually and do the leg work. Meet them face to face. See if there’s a vibe. It doesn’t have to be the love of your life. Have a nice dinner. Have a fun weekend. Have great sex. Focus on today. Stop ruining the moment right now making something out of nothing. He doesn’t need to be the father of your children but maybe he can be your sugar daddy for the weekend.

I’ve dated doctors and CEOs. I’ve dated homeless fucking losers with no jobs. I’ve dated construction workers. Trust me when I say I’ve dated a dude with every job type in the world (except an astronaut). And one thing rings true no matter how busy they are, how hectic their schedule: they DO have the time if they want to. I went out with a dude who worked 14 hour days and ran a trillion dollar office and would respond to me about wallpaper patterns but when he finally got sick of my shit, he’d take four days to respond to a simple text. I’ve been with men who had absolutely no job and still couldn’t carve out the time to return a phone call because they were soooooo busy. Being busy is a relative term and it simply means that if you’re important, he’ll find a way and if your aren’t, he won’t. We live in a world where people have their phones in their hands at all times, especially for work so if a man tells you that he doesn’t have time, he’s really just telling you that he doesn’t have time for you.

When we were younger, everything was about sex. Women grew up knowing (or should have at least) that the ultimate power was sex and once you gave that up, you lost all your cards. It’s a difficult game to play as we get older because we know our minds and our bodies so much more, and, at least for me, if I meet a guy and he’s kinda cute and kinda nice and kinda funny, I might just wanna fuck him. We don’t have to make a big deal out of it; let’s have a good time and see where it goes.

What I’ve noticed as we grow older is that these men we’re engaging with are getting older as well, and as they get older (and lonelier), the roles have reversed. You’re going to find a whole lot of men who don’t just want to fuck but want to hold hands, cuddle, spend the night, stare up at the stars and talk about their feelings, ALL WITH NO EMOTIONAL ATTACHMENT WHATSOEVER. We call this the “The Girlfriend Experience”.

Years ago when we were dreaming about meeting nice guys and getting married, they were consumed with getting their dicks wet. Now 20 years later, it’s a whole new world of independent women with their own money and lives who might just want to get Wined, Dine and 69’d, but these middle aged dudes want to be loved, held, and coddled because they might have fucked themselves into romantic obscurity and all that’s left are hookers and pass arounds. So the next time some guy wants to stay the night and talk about his mother, just remember what I said.

This one is particularly straightforward. In this case, when a man tells you directly what he doesn’t want, like a girlfriend, a relationship, or any type of personal responsibility to you in any way, BELIEVE HIM. Many times they’ll tell you exactly what it is in plain English in the very beginning, and you just chose not to listen.


Now, I will say, that while most all the other words out of their mouths are usually lies, it’s your responsibility to find the truth within and not fog it up with your own interpretation. I can’t tell you how often men tell us exactly what they think and exactly what they mean, and we choose not to pay attention. We think they’ll change their minds once they realize how wonderful we are, they’ll fall in love and decide they can’t live without us, or the dreaded “fear” excuse: he’s afraid of his feelings, he’s afraid to get hurt, he’s terrified to be in a relationship (I’m literally laughing so hard I pissed myself a little). These are all lies women tell themselves because we’re stupid.


If that man told you he doesn’t want a girlfriend, he doesn’t want you to be his girlfriend. If a man tells you you’re too good for him, it’s not a compliment. He’s telling you he’s a piece of shit; you’re just not listening. If a man tells you he’s not looking for anything serious, he means he’s not looking for anything serious with you. He either wants to be single until someone suitable comes along or he wants to be single, period. There’s no other option. This doesn’t mean sit around and hope he changes his mind because one week, one year, one decade won’t produce different results.


Listen to the words and apply them directly. It doesn’t matter how much you think he acts like he likes you: he doesn’t. He isn’t changing his mind. Not next week, not next year. So keep fucking him and getting your feelings hurt or cut ties and move on. It might hurt now but it’ll save you a lot of grief in the end, trust me.


Often times when you first meet someone, you start racking up all the good points, especially if it’s in stark contrast to the type of trash you’ve dated in the past. Has a form of income - check. Has their own place - check check. Doesn’t beat his mama - check check check. But this is where things can go wrong. This is some bare minimum shit and we think because they’re “ok” in contrast to others that they might really be something one day. Women wanna spend so much time hyping up a situation that could be instead of evaluating what it is. It sounds callous but you can’t keep dating a guy who might be great in six years and start asking yourself if he’s great right fucking now. Today. At this very moment. Do you like how he treats you now? Do you like how he makes you feel now? Is this situation doing something for you right now? If it’s not, move on. Simple as that. Stop wasting time on someone’s potential. He’s a man, not a sewing project.

Let me tell you a story. A few years ago this dude appeared in my DMs. He was never even on my radar but we ended up hanging out. It began to develop but with no acknowledgement of feelings or expectations. I began to like him a lot. A month before I went to see him, I cut my calories down to 1100 a day, did an hour of cardio seven days a week, and trained twice a day. I dropped 14 pounds in a month, had my teeth whitened, my lips plumped. I looked fucking fantastic, maybe the best I’d ever been in my life. Did he ever tell me I wasn’t pretty? No. Did he ever tell me I was too heavy? No. But I thought the better I looked, the more invested he’d be even though I looked like a homeless slob the first time we fucked. So I flew to see him and on day two he tells me he doesn’t want a girlfriend. Not because I wasn’t pretty. Not because I was fat. He didn’t want a girlfriend and didn’t bother to say so because (1) he was a self-centered asshole and (2) I didn’t make him. It wouldn’t have mattered if Megan fucking Fox got off that plane. He was in his fuckboy era and nothing was going to stop him. And I, deep down, knew it or I wouldn’t have killed myself to change something that was already perfect the way it was.


Sometimes things just are what they are, because of timing or the moon phase or he’s just a giant prick. You’re never going to be pretty enough, smart enough, thin enough for a man who doesn’t want you, for whatever lame ass reason. It’s never going to be enough because you’re not the problem; he is.


We all know it, that nagging, tugging, almost eerie feeling that something is wrong. An imperceptible change: the tenor of his voice, the frequency of his calls, a reduction in engagement, small changes in behavior and pattern. It’s called intuition and its a real fucking thing. Most of the time we tell ourselves it means nothing, we’re overthinking, acting crazy. Maybe he’s simply preoccupied with work or maybe he’s preoccupied trying to fuck that waitress from work. Either way, if you feel something the worst thing you can do is ignore it. Which goes hand in hand with #9…


For the love of God, open your fucking mouth and speak!! If something is bothering you, say something. If something hurt your feelings, say something. If you feel unclear or want definition, say something!!! If your gut is telling you something is wrong, the easiest and best way to get clarity is to say something. And the truth is that most women don’t say anything because they already know. Deep down in their hearts they are afraid that he’s going to tell them no he doesn’t want a relationship, yes he wants to keep fucking other people, and no he doesn’t fucking care so instead of speaking up, they just stay in this emotional grey area hoping one day things will magically turn out. Well a conversation is never going to ruin something that was real but it will certainly end all that fake shit. You just have to have the dignity to leave situations that were never meant for you. Trust me when I tell you I look back at 1000 times that I should have opened my mouth and spoke and regret every time I didn’t because it only prolonged the inevitable.


Plot twist. The outcome of dating is not how many dudes out there are pieces of shit. It’s not about how lackluster the sex is. It’s not about how cheesy the lines are. The only thing that really matters is you and the relationship you have with yourself. Dating can be fun or it can be a cesspool of fuckery but it affects a sad, lonely, desperate bitch quite differently than it affects a woman who is happy with herself and her life and can stay objective and level headed. Many times in the past I’ve thought OMG I’m going to die alone and honestly, I just might but I’d rather be alone than unhappy with someone else. As I get older and more secure with myself and what I want from life, the easier it is for me to cut mother fuckers off. Bad behavior, inconsistency, disrespect, lack of communication and I’m sending his ass right back to the streets because I’m looking for a grown man with simple life skills to spend my time with, not some oversized child who never learned the building blocks to an adult relationship.

It’s important to know what your boundaries are and to be firm about the consequences of crossing them, but you can’t do that if you’re a sobbing fucking mess trying to turn every ex-felon into “the one” because you don’t think there’s ever going to be another. Cut the shit and have some self worth for fuck’s sake. It’s not him bitch, it’s you. You’re the light in that duo. You’re the fun. You’re the spunk. You’re the vivacity. And if it doesn’t work out and you’re not getting what you want, cut the line and go find another to spoil with your amazing self.

XOXO, The Bitter Bitch