#1230: “Help Me Not Judge Myself If A Guy I Sleep With Turns Out To Be An Asshole Later” Hello Captain, I (she/her) have become rather adept at spotting red flags and parting ways when necessary. However, when I’m looking for casual sex, sometimes it takes away from the excitement if I’m getting to know the guy at length first. It’s, like, ‘let me interview you to know I like you as a friend before we have the not-so-spontaneous sex‘. It’s cool, but sometimes it’s not what I want. I’d rather have the amount of interaction that builds up to a sexy situation, then go for it. Then, if the guy turns out to be an asshole for some reason, I can cut ties with him and it’s not a big deal. But I’m worried I might end up judging myself along the lines of ‘you should have known better’ (and essentially internalising the judgement of family members / other people). Help me get looser! Lady on the Loose Dear Lady On The Loose, Respectfully, I don’t know how to tell you how to have a conversation between you and you, and I don’t think we can prevent our feelings even by thinking about them a whole lot in advance. “How do I stop myself from feeling ____” is a very common question in my box (right after ‘How do I tell people things they don’t want to hear but without making them upset?’) and the answer is the same: I don’t know, but I agree that it would be awesome if we could! What I have for you are questions: If you accidentally come across an asshole, it would be incredibly okay to feel bad about that, right? Assholes are unpleasant! What a crappy disappointing ruiner of your fun time! If you felt so bad that you started judging yourself, what would you do? What, if anything, would you change about your behavior and approach to casual sex and meeting men? If your friends and family judged you, what, if anything, would you change? Would you take a break from meeting people for a while? Would you institute stronger/slower/longer screening? Would you chalk it up to experience and keep going? You have options for adapting to new information, and feelings are one kind of information, so what’s the worst thing that happens if you trust yourself and say, “Hello, Self! I’ll definitely change it up if this stops working for us”? Be rigorous about safer sex practices and testing, and make sure you keep doing your due diligence re: safety and red flag spotting, but otherwise? Maybe getting what you want from this entails some risk, and this is one of the risks, and if it comes it comes, but you got what you wanted more times than you didn’t.

#1231: “Dickheads: Literal and Metaphorical”

Dear Captain Awkward,

About a year ago I was kicked out of my closest friend group. This partially happened because of a pattern of condescension directed towards me, but the Big Catalyst for the friend-breakup was that I asked the only straight guy in the group not to text me at one a.m., wink at me when everyone else wasn’t looking, make weird posturing/macho comments about my boyfriend and otherwise behave in ways I considered too flirty for me to be comfortable with. I asked calmly, and over a private DM. He responded with near-incoherent anger, repeating over and over that he was too feminist to behave that way and that he always respected women. He then showed the rest of the group the text exchange while I wasn’t there, and they all sided with him. This, by the way, was a predominantly queer friend group, where eight-paragraph lectures on why comic book characters pandered to the male gaze were commonplace.

Thanks to time, therapy, and your enormously helpful advice on how to find community, I’ve gained back my mental health, mostly gotten over that stuff and started to build a whole new network of friendships. But there’s one problem remaining.

I’ve started hanging out with a group of three guys in their early thirties. My gender inside my mind is mostly a giant question mark, but I’m perceived as a woman in her early twenties by the outside world. I really like these guys; they share my values, we have similar hobbies and interests and they’re a lot of fun to be around. They also seem really unlikely to pull the same shit that the asshole described above did.

But I still get nervous of really being open with them. I love raunchy/sexual jokes with most people. I want to talk openly about romantic/sexual relationships, since it’s such a big part of life. I’m bisexual, and I want to talk about attractive women and crushes and such. But when they mention dates they go on, I freeze up. When a stupid joke about dicks comes up, I feel like a rabbit in headlights.

Captain, I know rationally that I shouldn’t blame myself for my former friends’ actions. But I feel like if I am ever as open about internally flailing over a pretty girl or as explicitly encouraging when one of them is down about romantic prospects as I was back in the day with Asshole, I’m inviting that behaviour again. I also feel like Asshole’s behaviour was some kind of karma, considering that I too have handled an unrequited crush in really awful ways. How do I behave less prudishly, and be a bit more authentic around people who seem like really good friends?

– Imaginary Headlights (they/them)

P.S. To be clear, NONE of the three guys seems remotely like they would behave in the way Asshole did. This is entirely a my-head problem.

Dear Imaginary Headlights:

You could always try testing out something raunchy you want to say in small doses and seeing how the reaction goes, but my question for you is basically the same as the one for LW: If one or more of these new friends did react in a way that made you uncomfortable (if what you fear happens), what would you do about it?

Would you tamp down your comments or would you remind yourself, hey, I didn’t invite this in, and say something? “Well, that crossed the fun/not-fun line, are we going to have a problem?”

Human relationships are risk. Speaking up is risk. Your former friend group chose to keep their Missing Stair rather than risk a confrontation with him, what a safe and fun bet they’ve made! You trusting your new friends is going to be a risk, hopefully a good one.

Assholes gonna asshole. You didn’t cause your former friend to behave that way, you didn’t invite it all with your “karma,” he was a petty little harasser who got called out. You won’t never encounter one of those again, but you’ll spot them much sooner next sooner, and you’ll put up with so much less than you did before. That’s a win.

Both Letter Writers, you’re not ridiculous for feeling the way you do: People blame women and people they assume are women for the bad stuff cis straight men do to us with the same ease as breathing, unfortunately that lingering “if this goes bad is it going to look like all my fault” fear you have isn’t from nowhere. But it doesn’t mean we caused people to hurt us. There are red flag behaviors that we can start to recognize after a while, but it doesn’t mean that we brought bad stuff on ourselves by not recognizing them immediately or because a manipulative person successfully manipulated us; it’s not a personal failure to generally take people at their word and be optimistic about them.

Looking to the past to predict future behavior isn’t silly, it’s a survival strategy and it’s okay to look at someone’s actions and decide, whoaaaaaaaaaaaaaaa, that’s a bad bet (as in: the guy who was financially shady with his ex-girlfriend is going to be financially shady with you and every girlfriend he ever has, report identity theft and RUN!). LW #1231, if your former friend showed up promising that he’d changed, I’d take it with a shaker of salt. But these new friends? The frustrating, beautiful thing is that humans are very different and cautionary tales/case studies aren’t broadly applicable. If a person’s actions are telling you good things, their external resemblance to someone who did bad things in the past is probably coincidental, so excluding them from your life based on the fear that they might become just like the person who did the bad thing isn’t going to lead you anywhere happy. But you also don’t have to be “fair” about it, if you’re not ready to be open or risk the same thing happening, that’s okay, too! You get to decide your own risk tolerance, esp. in optional social activities!

Look at people’s actions, let that guide you, and if you end up trying to negotiate with your feelings, especially Future Feelings that Future You isn’t even feeling yet, use action there, too, like: “If this was a mistake and someday I feel the thing I’m so afraid to feel, what (if anything) will I do about it?” Feelings are coming one way or another, you aren’t the boss of them but they definitely aren’t the boss of you, either. What if you could make friends with your feelings, invite them in, and see what they have to tell you? You can decide what to do about them after a nice chat and some tea.