Is It Possible to Get Better at Dating Without Being Creepy?

Dear Dr. NerdLove: Is it true that dating, attraction, flirting, initiating contact and escalating and knowing when to do them, etc. are skills and like all skills, require making mistakes in order to get better?

The reason why I’m asking is that, based on everything I’ve read, these are all skills you can improve at. Virtually all skills require you to make mistakes and learn from them in order to get better. However, making mistakes while learning these skills are almost certainly going to lead to awkwardness at best, anyone you attempted to attract fearing you or hating you at worst. Most likely, a guy who makes a mistake doing this is going to be labeled creepy.

It really feels like a hostile environment for any man trying to learn dating skills. It seems like the expectation is that men must be absolutely perfect from the start. Yes, I’m aware that women do this for their own safety, better safe than sorry, it’s better that they label a guy who meant no harm creepy than a guy harms them. Because I can’t prove a negative, that I’m not creepy, it just feels impossible to get better at this.

So am I completely off the mark here?

Don’t Wanna Be The Guy

You’re making a common mistake, DWBTG; you’re starting from a reasonable premise – dating is a skill, practicing a skill means making mistakes – and veering off into the entirely wrong direction based on fears, not facts.

The problem you’re having is that you don’t know what you’re talking about. I don’t mean that you’re stupid or ignorant; it’s that you don’t know what you don’t know and you’re making incorrect assumptions because of it. Since you aren’t fully aware of what you don’t know, you’re filling in a lot of blanks based on suppositions and false premises. Worse, you’re taking those suppositions as given and drawing a lot of mistaken conclusions.

So let’s fix that, shall we?

Your first incorrect assumption is the difference between a mistake and failure. A mistake is a choice; failure is not. Failure can happen because you made a mistake, sure… but you can also fail without making a mistake, simply because you don’t have the actual skill or experience to do it correctly.

When you’re learning a new skill, you’re going to fail at it fairly often. But failing at something, especially because you’ve never done it before, isn’t a mistake. You just don’t have the experience to know how to do it correctly.

When you were learning how to walk, you fell over a lot. You weren’t making mistakes, you were just dealing with things you’d never experienced before and you didn’t have the muscle strength, coordination or proprioception to do it successfully. You developed those in time and now you’re walking without thinking about how mechanically difficult a feat you’re accomplishing.

But that’s for babies. What about when you’re a grown-ass adult? Or at least, someone who’s over the age of, say, 2. In fact, let’s say that you’re just starting to learn how to play basketball. You’ve never dribbled, passed the ball, never even played a game of Horse. If you try to shoot the ball and miss, you didn’t make a mistake, you just failed to sink the basket. If someone passes the ball and you miss, that is a failure, not a mistake. If you pass the ball to the wrong person then yeah that’s a mistake. But that’s often a failure of skill, rather than a poor choice – you’re not used to the chaos of a game, you don’t have the experience to know how to focus and spot the teammate who’s open… all of these things are accomplished through practice.

And skill and experience don’t prevent you from making mistakes. You can see people – incredibly skilled, talented people – make mistakes all the time. The fighting game champion who misjudged the timing of a block or combo, the concert pianist who got flustered and missed a note, the chess player who got out-maneuvered by their opponent or missed a critical opening. Those are all mistakes that even the best of us can make, because we’re all human and we’re all imperfect.

The second false assumption you’re making is that you can’t make mistakes when talking to women. This isn’t true at all, and it’s born out of the false premise that talking to women is like defusing a bomb – so much as look at the wrong wire and suddenly you’re created a massive faux pas and the whole interaction has blown up, messily and all over the place.

The corollary, of course, is that if you do everything perfectly then you’re guaranteed a date or for everything to go well. And that’s not true, either. As the man says: it’s possible to commit no errors and still lose; that’s just life. This works both ways – you can make mistakes and still win.

But for this to be true, that would mean that women are actively looking for reasons to disqualify you and that’s just not the case. In fact, that mindset is going to cause more problems than just assuming that people like you.

Here’s the truth: 99% of the mistakes you make are barely noticeable, and most people won’t even care. Certainly not as much as you do. And they’re certainly not actively looking for you to screw up.

Have you ever walked into a place and thought someone was waving at you, only to realize that they were waving at someone else? You probably felt like you wanted the earth to open up and swallow you whole when you realized, hand half raised.

Guess what? I can guarantee that nobody noticed, and if they did, they forgot the literal second you left their eyeline. And just about everyone can relate to that exact experience; they’re not going to judge you for having done it, because they understand exactly what you’re feeling in that moment and they’re going to empathize.

Nobody is expecting perfection and everyone’s made mistakes. If someone likes you, then they’re going to be a lot more forgiving than you’d think. But even if they’re someone you’ve just met, making a mistake isn’t an instant fail. Most of the mistakes you’re likely to make – especially when you’re learning – are pretty minor and easily overlooked. Trying to start a conversation with someone who’s not actually interested in meeting folks? Embarrassing, a bit of a sting to the ego, but not a big deal. Asked someone out and they have a partner? Or they’re not interested in men? Well, there’s literally no way to predict that, and most people aren’t going to be offended. Many will be flattered, most will be cool and all of them just want you to not be an asshole about it.

You have to make some pretty big mistakes to really be a creeper. It’s certainly possible to make a big mistake – and I’m speaking from personal experience here – but that tends to require actual carelessness or disregard for other people; the likelihood of your stumbling into making a major error by pure accident is so low that you’re more likely to be hit by space debris. Indoors.

Nobody is expecting perfection. Everyone understands that people trip themselves up. And part of the point of making mistakes when you’re learning is not just to learn how to not make mistakes, but how to recover from them when you make them. You’re going to make mistakes because you’re human, just like everyone else. If you think mistakes are an instant-fail condition, you’ll never accomplish anything for fear of the slightest error.

The final misconception we’re dealing with here is what actually makes somebody creepy. When we’re talking about someone being a creeper – an actual creeper, not the fantasy of “it’s only creepy if you’re ugly” hand-wave that dudes throw around – we’re talking about behavior that make people feel unsafe. If, for example, you were to show up unexpectedly and surprised someone because you saw something in their Instagram that told you where they were? That can be unsettling. If you made it clear that you could always find them based on what they post? That’s going to move it past “unsettling” into “yup, that’s creepy” – that suggests that you can find them at any time, and they can’t stop you. Are you consistently touching them in intimate ways and missing or ignoring their discomfort? Yeah, that’s going to be potentially creepy; you’re signaling that you either don’t recognize signs that they don’t want to be touched or don’t care that they don’t. The former is unnerving. The latter is creepy, because you’re stating that you don’t see their comfort or disinterest as mattering. That’s the point where you’re starting to be an actual threat.

Most of the things that make you creepy aren’t going to be casual mistakes, they’re going to be behavior that signals a disregard for other people’s comfort or security. The guy who tracks a stranger down over social media after having met her once is being creepy, especially when he does so in order to try to get a date or sex from her. The guy who turns every conversation sexual, no matter how other people feel? That’s creepy because he’s violating people’s boundaries; they don’t want to talk about sex with him and he’s decided his interests override their disinterest.

But let’s say you touch someone and realize that they’ve tensed up and aren’t comfortable with it. If you realize what’s going on, pull your hand back, apologize and – critically – don’t make that same mistake? You’re on much safer ground. It may have been uncomfortable, but you’ve demonstrated that it was an honest mistake, you regret it and you’ve learned. Made a comment or joke that didn’t go over, that tripped a particular issue for them or otherwise shoved your foot in your mouth? Same thing: apologize and learn from it.

Now, are there folks who will have stronger reactions to genuine mistakes than others? Of course – individuals will vary wildly for all sorts of reasons and it’s literally impossible to factor that into every interaction you’ll ever have. But if you follow some best practices – especially if you get in the habit of asking or using your words, rather than just guessing or plowing ahead without care – and you’ll be far less likely to step on a landmine you had no idea was there.

Do women live in a world where their safety is far from guaranteed? Yes. Do they experience danger in ways that men don’t? Of course. Does that mean they see every man as the enemy or see every slip-up as being a sign that he’s a serial killer? Of course not. Women have plenty of reasons to be on their guard, but there’s a difference between understandable caution and out-and-out paranoia. If someone starts to hate you because of an honest mistake? That tends to be an issue with them, not because you fucked up that badly.

As you learn, yeah, you’ll make mistakes and you’ll have failures. You want to try to keep those to a minimum, but you also need to understand that they happen and that they’re not the end of the world. If you’re moving through the world with some compassion and empathy for others and act with actual understanding – rather than making unfounded assumptions – then you’re going to be doing better than most. Learn from the mistakes you make, apologize when you do, avoid making those same mistakes again and you’ll be ok.

Good luck.

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Dear Dr. NerdLove –

My friends and I have a problem and we hope you can solve it. We’ve got a friend – let’s call him Carson. Carson’s a great guy, he’s been my friend for years and he’s a valued part of our social circle. Carson’s not the problem… his girlfriend “Molly” is.

We don’t like her, at all. I don’t really have any better way to describe Molly except to say that she’s just a bitch. You can’t have a conversation around her that she doesn’t try to take over and she talks over everyone. She makes everything about her, constantly. If you had a problem, she’s had a bigger one and so much worse. If you had a good day, well better hope she didn’t have a bad one or she’ll remind you about how lucky you are because SOME people (except she means her) had a bad one or have some horrible thing in their lives and it’s rude of you to be so happy about your thing.

She’s an Expert In Everything (she looked it up on Google once or read some Tumblr post on it) and will correct people who actually know what they’re talking about. She’ll lecture folks about all of their sins for not being woke enough or liking “problematic” things, criticize you for talking about things she doesn’t view as being good or pure enough and remind you that SHE would never do such things, that’s for bad people. And if you point out that she did the exact same thing, then she’ll have any number of reasons why it didn’t count when SHE did it. And of course, she has no problem making these constant left-handed compliments or passive-aggressive remarks about people. I think you could say she’s negging us, except I don’t think she’s interested in ANYONE that way.

Everything has to be exactly how she wants it and if it’s not perfect, she’ll throw a tantrum. She won’t rant and rave (unless you’re a waiter who didn’t get her order “right”), she’ll get passive-aggressive and pout and give folks the silent treatment if you’re lucky. If you’re not, she’ll start complaining constantly and just be the biggest wet blanket while the rest of us are trying to have a good time. Then Carson has to try to make her feel better which usually involves a lot of apologizing and promising how he’s going to make it up to her and “fixing” things becomes incredibly inconvenient for everyone. So if we want to hang out with Carson, it means we’re stuck with whatever Molly’s willing to do and nothing else.

Normally we’d just ignore her or try to avoid her but she is ALWAYS around. She won’t let Carson out of her sight and if he’s out on his own, he has to check in with her constantly. She has no problem texting him and demanding he drop whatever he’s doing for her, but if you do anything to inconvenience her in any way, she’s going to demand that you account for yourself and listen while she explains why you were wrong. And if you object, that just proves how wrong you are and why she’s right to correct you. She’s doing it to make you better, you see.

Honestly, we’re worried about saying anything to Carson because, much as I love the guy, he’s a complete puss when it comes to her. He’s not the most assertive guy even before he met Molly but he’s gone completely spineless since he started dating her. We’re worried that if we say anything, she’s just going to start forbidding him from seeing us. It’s hard enough getting time with him without him as it is.

Dr, we tried. I swear we did. We tried to give her a chance, and we’re all thoroughly sick of her. What do we do? How do we tell our friend that his girlfriend’s a bitch, without her just pulling him away from us?

Help!

Saving Silverman

Hoooo boy.

OK, SS, I’m gonna level with you: reading your letter was rough because I’ve been there, I’ve done that and I owned the T-shirt factory. The problem is that I was Carson and this Molly sounds far too much like my ex.

Now, I’ve talked about my own experiences in a toxic relationship before, but there’s one aspect that I want to zero in on: I knew that my friends didn’t like her much. The problem is that I wasn’t ready to hear from them that this was a bad scene. I wasn’t in a place where I could actually recognize just how bad things were, no matter what my friends said. I got very good at rationalizing their reasons away, explaining – to myself or others – why they were mistaken or misunderstood her and it wasn’t that bad. There was always a perfectly good reason why this thing or that thing she did was actually acceptable if people would just understand or see it from her side of things or…

Well, I’m sure you see where this is going.

My point is: I’ve been where Carson is, so I can tell you from experience: there’s not much you can do. Carson’s going to have a lot of Very Good Reasons that explain Molly’s behavior and why it’s Ok, Actually.

(It’s an open question as to whether he actually believes that or he – like me, back in the day – isn’t ready to face that it’s a bad scene.)

And you’re not wrong to be worried that Molly might use this as an excuse to pull Carson away. If she already can dictate how he spends his time or demand he leave you all and go back to her, then it’s certainly possible – even likely – that she’d isolate him from you all if you talked about her.

But then again, she may do it anyway. Not saying anything isn’t going to be a guarantee that she won’t just continue to isolate him from his friends, so you may as well say something.

However – again, speaking from experience – it needs to be handled the right way, and with the understanding that this is going to be a process, not a one-time conversation.

What I’d suggest is to get time with Carson by himself. Now to be clear, this time with Carson should be standard “hanging with friends” time, not an intervention. If there’s even a whiff of confrontation or judgement, his guard is going to go up and he’s going to get defensive very quickly. As soon as he’s in a defensive stance, he’s going to stop listening. You want to avoid this as much as possible, for as long as possible. You’re likely going to trigger that defensive posture at some point, but the longer you can put that off, the better.

You’re not going to be able to change his mind for him; instead, you’re going to have to entice him to change his own mind. If he’s going to get to a point where he’s ready to see this as a bad situation then he’s going to have to decide that on his own. All you can do is light the path for him.

I’d start with casually mentioning that it seems like you don’t get to see as much of him as you’d like, certainly not just him. The “get” is important; the underlying message is that he’s not “allowed” to spend time with you. When he shrugs it off or says he’s been busy, you can say that it seems like Molly demands all his time or doesn’t seem to like him spending time with you all.

Whatever he says to this, the next thing to point out is that it seems like Molly isn’t… really a happy person. She always seems to have something going on and she’s always upset about something. And well, you’re worried that he’s having a hard time right now with the way she’s always just in a bad mood. You worry that maybe it’s affecting him too, especially since he doesn’t seem to get time away from her. How’s he doing? Is he doing ok? You might also mention that maybe he doesn’t seem like he’s all that happy right now or that he’s been down for a while.

If Carson’s not stupid – and it doesn’t sound like he is – he’ll probably pick up on the subtext. He may ask you straight up if you don’t like Molly or if you have a problem with her. If he does, then the best thing you can say is that you all get the feeling she has a problem with you all and she just doesn’t seem like she fits in with the group and that makes it hard to get time to see him.

Now if he wants to make it about what you don’t like about her, don’t respond with specifics. Instead, you’d do better to ask questions. Is it you, or does it seem like she complains a lot? Does it bother him when she talks over him? Or maybe ask why she makes the comments about your friends? Does he ever feel like he can’t stand up to her, or does she always get her way in the end? Doesn’t that get frustrating?

If he still won’t let go of the idea that you don’t like Molly, then it’s time to tell him the truth. The best answer you can have is “I worry that she’s making you unhappy”. He’ll have an answer for this; he’s not ready to admit that there’s a problem. But the important thing is to focus on him, not her.

Keep in mind, all you’re doing here is trying to sow the seeds of doubt, ones that lead to him coming to the conclusion you’re hoping for. That’s… not going to be easy. You’re going to have to spend a lot of time waiting for those seeds to bloom, and a lot of them won’t. So don’t be confrontational, be concerned and empathetic and wanting things to be better. Reminding him that you care about him is going to be crucial.

Now, having different members of your friend group have similar conversations – mostly how you don’t see him, Molly takes all his time, he seems down is he ok? – can help a bit, but odds are that he’ll twig to what’s actually going on pretty quickly. If you want to keep him from getting defensive, you’ll have to tread very carefully.

Now if he does get defensive, then that’s your clue to let the conversation go. Make it clear that you’ve said your peace, you’re going to drop it, but you are always going to be there for him. If he wants to talk about anything, you’re there to listen, no questions asked, no judgement given.

And that no judgement is going to be important. If Carson does recognize that his relationship with Molly is bad, he’s going to feel pretty ashamed about it. Knowing that he can come to you or any of his friends without getting an “I told you so” or jokes at his expense will be important. If he feels like he’s going to get so much as a whiff of mockery or embarrassment, he’s not going to reach out to you. Yeah, it seems crazy that someone would rather stay in a potentially abusive relationship than face some embarrassment. Welcome to the human psyche, we’re all just apes with anxiety, nobody expects us to be rational actors.

Do your best to spend time with him without Molly, remind him that you all are all there for him no matter what and generally show him that life without her around is better.

But more than anything else, make it clear that the lines of communication are always open and you’re there for him, no matter what. Knowing that he can come to you at any time will make it easier for him to finally leave her when he’s ready.

Just be prepared for that to take a while. It may suck, and it’s incredibly frustrating, but it’s ultimately going to have to be his choice. And he won’t make that choice until he’s ready to do so.

Good luck.

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This post was previously published on Doctornerdlove.com and is republished on medium.

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