DEAR DR. NERDLOVE: So, a couple years ago I sent you a letter about how to be more vulnerable and open up to others. This is my update on that, with a follow-up question.
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Your advice was helpful, and over time, I did largely achieve it. Friendships are better, and I became a trusted and well liked figure among friends in and out of work, with many even opening up to me more with some of their own vulnerabilities. Not just listening, but making people feel heard and understood, was the key. That front has turned out well.
I had also mentioned a cute new hire I was interested in; ironically enough (not in the fun way), not long after that letter, things had gotten hectic at work with very few physical opportunities for us to talk. We rarely saw each other, or even were in the same area; and while I did work to make our limited interactions count, we didn’t start talking more regularly until late last year/early this one.
From there, we hit it off really well, and grew close as we got to know each other. She has a lot of the personality traits I like in a woman, and I developed deeper feelings. It seemed she was interested too, so I asked her out recently. She didn’t feel the same way, but I accepted it with dignity, and we are still good friends.
The spectrum-dweller hindsight in me of course went over the main things I did wrong. I still don’t know how to flirt (or otherwise escalate a conversation/relationship beyond the platonic realm). And I know that’s very tricky to do well in the work environment, but there were times where she and I would meet with work friends outside the office, and I could have done so there if I knew how. I’ve also developed a low-key confidence that’s been great for my mental health overall, but has had no effect on my dating life, as it’s not the more overt sort that most people consider attractive.
So, here’s my new question: how do I become more bold? Both in everyday encounters, and when interacting with women I’m interested in?
I do want to clarify that I will need specific steps/practices that I can adapt to my natural style. It’s hard to find advice on this topic this isn’t generic and useless – i.e. “just practice flirting,” “just practice your social skills,” “just practice being confident/bold.” It’s like a chemist asking you to hand her the nitric acid, when none of the test tubes are labeled, and all their contents seem to be the same. The “advice” assumes you already know how to do it well, and tells to just keep doing it, when you have no clue of where Square One even is. And I know you like to go in-depth with this sort of topic.
Because despite the social success I’ve had, it hasn’t reached the point of building attraction in others. I’m lacking that bit of edge, of fire, of spirit that sparks it. The thing that puts one on the list of potential dating/sex partners. And developing this boldness can help avoid missing opportunities, like with the friend I asked out.
And yes, I know her feelings may change down the line, especially if I do become more bold; but, I’m obviously not expecting it. I can, however, cultivate the skills needed for future prospects.
Please and thank you,
Your Friendly Neighborhood Memelord Returns
DEAR YOUR FRIENDLY NEIGHBORHOOD MEMELORD RETURNS: Right off the bat, I’ll remind you what I’ve said about flirting, over and over again: it’s simply the act of letting someone know you like them in a fun and charming way. There’re as many ways to flirt as there are people because there’re an almost infinite number of ways to flirt from being direct to being coy, being as overt and aggressive as Pepe Le Pew asking someone to come wiz him to ze Casbah, to someone being adorkable as they stammer their way towards asking someone out on a date. Part of learning how to flirt is learning what style of flirting resonates best with your personality and the people you’re most interested in. Not everyone is going to be into semi-antagonistic bantering back and forth, just as not everyone is going to be into being incredibly direct and forthright. You can look at examples of how other people flirt and try them out for size (and I recommend it, especially while you’re figuring your own style out), but at the end of the day, your flirting style is going to be unique to you.
Similarly, you’re dealing with a fundamental misunderstanding about what being bold is. Being bold isn’t about a series of steps, it’s a mindset. Boldness is, put simply, the state of not being afraid of the potential consequences of those actions. To give an example from Star Wars, when Princess Leia says “Darth Vader, only you could be so bold…”, she’s commenting on the fact that Vader has done something that many would see as reckless, even foolish: attacking a counselor’s ship on a diplomatic mission, something that would presumably result in negative consequences for him when the Imperial Senate hears about it.
Vader, being a Sith Lord, could not give less of a f--k. Leaving aside that he knows for a fact that the plans are on the Tantive IV, Vader is power personified and feels (correctly, in this case) that there is nobody in the Empire who has the power to overrule him or enforce consequences. Neither Palpatine nor Tarkin are going to disagree with his actions, after all.
Hell, on a meta level, George Lucas making Star Wars in the first place was a bold decision. He not only was making a high-budget sci-fi film in a time when sci-fi films weren’t big money makers, he did so while also choosing to hold onto the licensing rights in lieu of a higher share of the profits. That’s a pretty big swing and a bold decision to make, and one that clearly paid off for him… but it was a very big risk to take.
This is why the process of becoming bolder is, quite simply, the process of not being so afraid of the potential negative outcomes of a particular action, or deciding that the positive outcomes are either more likely if you take this action or that they outweigh the potential negative consequences.
Being bold in a dating or flirting context would mean taking risks and making bigger swings than other folks would. This doesn’t mean that the risks are always real, mind you, just perceived. Being bold might, for example, mean confidently asking out the most popular girl in school even if you’re not one of The Cool Kids. Or shooting your shot with someone who is supposedly “out of your league”. Or going over to chat someone up even though there’re three other guys already talking to her.
The theoretical risks are myriad. You might get laughed at. Bullies at school might decide to punish you for your presumption. Those other guys might get upset and violent at your trying to horn in on their action. Or nothing might happen; you get no reaction at all or the entire conversation never goes beyond initial pleasantries. Or you might get that sexy somebody’s phone number… and that would be well worth the risk.
This is why there’s no step-by-step instruction manual for being bolder and why people who tell you to practice it aren’t just giving you the run around. You practice being bolder the same way you practice flirting or the same way you practice making goals in soccer or shooting baskets in basketball: you perform that particular skill, over and over again. If you’re practicing soccer, you’re doing the actions that you would perform when you play soccer – dribbling, passing, shooting, working with your teammates and so on. When you practice flirting, you flirt with people. You may not be flirting with intent – that is, you’re not angling for a date or to get their number or their WhatsApp profile – but you are flirting. When you want to practice being bold, you take bold actions instead of taking safe or less risky ones.
And this is important, because being bold is a choice you decide to make each time the opportunity arises. It’s not about taking the longshot every time, it’s about simply deciding in each instance whether this is a time to go for broke or not. Sometimes it is, sometimes it isn’t. Someone who’s bold may make the call to take the big swing more often than not, but they don’t do it every time. They weigh their odds and make their decision in the moment. Do you take the risk – either under the assumption that the odds are in your favor or under the assumption that failure would cost you less than what success might bring? Or do you play it safer, mitigate the risks but at the cost of potentially missing out on the greater reward? Is this the right time to make that play, or is it better to wait?
Part of what makes it practice is that your goal is to learn, not necessarily to succeed. When you’re doing passing drills in sports, you’re doing so to develop the skill to the point of muscle memory; moving from conscious incompetence to conscious competence to unconscious competence. If you have issues getting the ball to the right person, you figure out what mistakes you’re making and work on correcting them. When you practice flirting, part of what you’re doing is figuring out what works for you, what doesn’t, and why. Is it not working because it’s something that you’re doing wrong, or is it because it’s not congruent with who you are? Is it something you said or is it just that this isn’t the right person? When you practice being bold, you’re figuring out how accurately you measure risk, how well you gauge your skill vs. that risk and whether those risks are worth the reward.
Please notice carefully, however, that I don’t say anything about success or failure. Being bold isn’t about success, it’s about the attempt. You can be bold and still fail, just as you can play it safe and possibly succeed. It’s just a question of whether you’re willing to make a bigger swing and take a higher level of risk for that reward.
So if you want to be bolder, the answer is to be bolder. To take shots that others might not, to take bigger swings that might not work out, in the name of a better outcome than you would get by being more measured or more careful or more restrained. To be bold is to be comfortable with risk and with the potential of failure. That only comes about by actually doing it and not letting failure rattle you.
So take some bigger swings and see what happens. If you fail, what can you learn from that failure? If you succeed, is that success replicable, or was it luck? Did you read the room accurately or did you fall on your face and are you willing to try again? Was the outcome worth the effort, or was this an area where making a bold move was a poorer choice? The more confident you become in your decisions and in yourself, the more often you’ll feel empowered to make a bold choice and take that risk.
Good luck.
Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com