DEAR DR. NERDLOVE: So I have an issue that is a bit frustrating and that I’d like your advice on, as I’ve been reading your work for years (and have written in a few times) and look forward to seeing what you have to say. Now, for the matter at hand.

Recently (as in the past 3 or so months), I’ve decided to start putting myself out there after my relationship with my ex-boyfriend of almost 3 years ended last October. I have online dating profiles but the world of online dating is absolutely maddening, and for a gay man, like myself, it’s nearly impossible. So I thought I’d try my hand in the real world.

For about a year now, I’ve been working as a receptionist at a car dealership. To get to the meat of things, I get a lot of cute guys coming in and out of my dealership. Great opportunity to practice my flirting, right? I thought so too before I was faced with the crushing realization that I’m not as good at flirting as I thought I was. No matter how attractive I find these guys, all I can muster up is a smile and a “have a great day.” I don’t really know what else to do or say.

I’d love to hear what advice you have for me, if any.

Thanks,

Lonely and Frustrated

DEAR LONELY AND FRUSTRATED: First things first, LaF: don’t hit on people when you’re on the job. Not, at least, if your job doesn’t entail being professionally flirty. It’s one thing if you’re in a service industry position, in a job where your income depends on tips or commissions; there’s an expectation of sorts that you’re going to engage with the customers on an emotional level as much as a professional one. It’s another when you’re expected to be someone who helps facilitate a smooth business interaction between customer and company. If you’re not in a position where being a little flirty is expected or understood to be part of the gig, then it runs the risk of being off-putting or making people uncomfortable, even when that’s not what you intend. That’s a good way to end up without a job.

But hey, let’s assume a frictionless environment where you’re free to flirt as much as you want without fear of consequence. How do you get better at flirting with people? The obvious answer is: by flirting with them. Flirting is a skill, and like all skills, it’s one that you develop and improve through deliberate use.

However, we don’t give credit for incomplete answers around here, so let’s expand this a little more. Flirting isn’t as hard or as complicated or even as scary as folks think. At the end of the day, all flirting is about expression, entertainment and persuasion. If you keep this in mind, then you open up an almost infinite number of ways to flirt, ways that are as unique and different as you are. In my column “What Men Need To Know About Flirting”,  I cover a number of examples of different flirting styles, ranging from humorous and banter-y to intense and serious. However, your flirting style is the one that best suits your personality and – ideally – the personality of the person you’re flirting with.

Think of it this way: you’re at a pool on a hot day. The water’s crisp and cold and wonderful. You are in the pool. The person you’re interested in isn’t. How would you persuade them to choose to get in the pool with you? Would you talk about how great the cool water feels tracing down your body in the hot sun? Would you play up how much fun you’re having in the pool and invite them to join you? Are you the sort of person who would splash around a bit and try to bait them into splashing you back? Perhaps you’re more of a reverse-psychology type who would tease them about how the water’s just too cold for them and they’re better off staying out where it’s dry.

In all of these cases, what you’re ultimately doing is giving them a reason to want to get into the pool with you. You’re not changing their mind for them, so much as giving them permission to do a thing they already want to do… even if they weren’t necessarily aware that they wanted to do it yet.

Thinking of it in terms of “get them to get in the pool with you” is useful, because you need to tailor you approach both to your personality, but also to the personality of the person you’re flirting with. After all, just because you may be a rambunctious, mischievous sort who delights in soaking others, if the person you’re trying to persuade doesn’t go in for roughhousing, then splashing them is only going to piss them off… the opposite of what you want. Similarly, if you’re a more serious person, talking about the benefits of a nice dip may be a bit boring to someone who’s a jokester or likes to play. Finding the right balance between your flirting style and their personality is more art than science, but it’s a balancing act that you want to try to master if you want to get better at flirting with hot dudes.

Now what you don’t want is to go hard core with the flirting right off the bat, especially if you don’t know the other person. It’s best to start very lightly, with an air of almost plausible-deniability. Think of it like a sonar ping; you’re trying to pick up on if there’s anything out there without giving your position away right off the bat. If there’s a little mutual interest, they’re in a position to respond positively and you can escalate things by measures. If there is no interest, then they’re free to pretend to miss the flirting without necessarily making things awkward.

Plus, as a gay man, you’re at risk if you try flirting with someone who’s a homophobe; keeping things light and friendly but plausibly deniable helps keep you safe as well.

Above all else, however, your goal when you flirt should be about having fun and expressing interest. Fun is the vital core of flirting; if everyone’s not enjoying it, then it’s no longer flirting. You can flirt with intent, or you can flirt without intent, but if you and the person you’re talking to aren’t having fun, then you’re doing it wrong.

If you can find some places where you can do a little sport-flirting without fearing for either your job or you physical safety, then that’s perfect; you’re able to get some practice in and work on building that skillset in a fairly efficient manner. Otherwise, you’ll need to be work on getting into the habit of just talking with people first, then branching into flirting when you’re not feeling yourself freeze up just because you need to say more than a couple words to a hot dude at work. The folks who tend to be the best at flirting tend to be skilled conversationalists after all, and aren’t necessarily afraid of chatting with strangers.

But there’s one more thing to consider. While flirting is a skill, and a helpful one to have, it’s not one that you need to be super skilled at, or be able to do perfectly. Even awkward flirting can work out, especially when everyone involved is having fun. The fact that you’re doing it at all is frequently more important than doing it well, and for many, that enthusiasm-over-skill gap is actually really appealing. There’s a reason why “adorkable” is a thing, after all.

So figure out your flirting style and give yourself permission to do it imperfectly, even to mess up and make mistakes. The important part isn’t about having a silver tongue and the gift of gab, it’s the fact that you’re making your interest known and having fun with someone you’re into.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I wound up becoming friends with someone I developed romantic feelings for and I f--ked up. First off I was too pushy when it came to wanting to date her and I kept pressing the question as it was the first time I felt the desire to pursue a romantic relationship with someone.

However, before I wanted to be with her I kept getting hung up on if she could read my intent to be in a romantic relationship when I texted her. I worry about that a lot actually as I am asexual and I don’t desire a sexual relationship but I still worry if that comes across anyways. Even when I contact people I don’t want to be in a relationship with, I just worry that I will wind up annoying them. I want to know how I can stop this nagging feeling and just get more comfortable with not interacting with people in person.

I also want to know if it’s possible to salvage any friendship with this girl and how do I stop things from being weird in the future.

A Confused Asexual

DEAR A CONFUSED ASEXUAL: The pushiness you’re describing is a symptom, not the underlying condition, ACA, and it’s important to keep that in mind. You can, for example, find various ways to consciously stop pushing people for a reply or a result… but you’ll still be feeling the tension and worry and stress on top of having to devote a lot of your mental bandwidth to the action itself.

What you’re dealing with is a sense of insecurity. There’s a part of you that doesn’t feel enough, that you aren’t “worthy” or have intrinsic value, and that leads to the worry that others will recognize that and leave or abandon you. Getting pushy about dating someone or demanding answers is, in some ways, an attempt to lock them down before they could realize that they could “do better”. That gets twisted up with a scarcity mentality (“I’ve never felt this before, I will probably never feel this again for anyone else, therefore it’s vital I make this happen”) that leaves you worried that if this person rejects you, then you’ll never feel this way again. It feels like your last chance for love, companionship, a relationship… you name it.

Now, on its face, this makes it sound like your being pushy or worried about annoying others is a flaw or a negative behavior, something that “better” people don’t do. And in fairness, that’s how I treated those sorts of behavior in myself when I was younger, and it informed my approach to dating and teaching others. But what I’ve learned over time is that this mindset is counterproductive. It puts you in a place of self-recrimination, which only ends up exacerbating that sense of insecurity.

Instead,  you want to understand what those actions mean, the why of them. Because while the net effect of the pushiness may be negative, the reason for those behaviors is ultimately self-protection. You’re trying to protect yourself from being hurt or rejected; it’s just that the way that you’re going about it isn’t helpful. That doesn’t make you a bad person, just that the way your subconscious is going about things is proving counterproductive.

So rather than getting upset at yourself for being pushy or anxious, I think the best thing you can do is acknowledge what you’re trying to do and be appreciative for the intent, but also that those behaviors aren’t serving your needs. You can correct your behavior here without needing to go into a shame or blame spiral.

As you do this, I’d recommend focusing on cultivating things that make you feel good about yourself – finding the things that make you feel like your life is awesome. Part of overcoming insecurity is learning how to connect to your own sense of value and self-esteem; living a more conscious and directed life goes a very long way towards that.

Part of what leaves us feeling insecure is a sense of helplessness or a lack of control. When you feel helpless to actually steer your own existence, the vulnerability required to date or tell someone how you feel becomes even more terrifying. You feel as though you’re left at the mercy of the whims of others, and if you don’t feel secure in yourself… well, that’s often a terrifying place to be.

When you have more conscious control over your life and consciously bring things into it that make you feel good about being you, then you don’t fear that vulnerability as much. Yes, you can’t control how other people feel, but it also means that you aren’t left feeling that finding this person was a cosmic fluke that may never happen again. You create a mental framework that says “Well, I brought myself to this place where I met this person and it didn’t work out; I can bring myself to a place where I’ll find someone else just as awesome who also wants what I have to offer.”

So fill your life with things that you’re passionate about, things that make you feel like an awesome badass. Work towards things that make you go “yes, damn, that’s great!”, even if it’s some weird thing that only you could like. Letting yourself love and enjoy things unabashedly and that makes you love life helps build up that sense of security and internal validation; that, in turn, makes it much easier to not feel the need to push for a response when you do find yourself developing feelings for people.

Because here’s the thing: if you feel secure in your own worth? Then it’s much easier to say “Ok, I put the offer out there, ball’s in their court. I don’t need to do anything more. They’ll either get back to me or they won’t and I’ll be ok either way”.

And a good place to practice that feeling would be to send an apology to your friend. A simple “Hey, I’m sorry I’ve been so pushy about things. It wasn’t cool of me and I won’t do it again. I hope we can still be friends/be friends again.” will go a long way. But like I said: send that and then leave the ball in their court. Letting her decide if she wants to accept your apology and what she wants to do next, in her own time, will demonstrate that you understand and that you mean what you said.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: Proud patron of yours here and I’m happy to be writing in after years of reading your enormously helpful columns and watching videos. Thanks for all you do — I’m in a very satisfying relationship that’s about to cross the one year mark due in no small part to heeding your advice. You’ve written and spoken a lot about how to become a confident person — where confidence comes from, how to develop and reinforce it, how to fake it ’til you make it, and so on. All of it, practically every word, has been essential to pushing me in a more confident direction for sure.

I’ve begun to notice, though, that a lot of self help advice, and even therapy in my experience, seems to focus on the more practical, actionable aspects of confidence building and self-acceptance. One thing that I don’t see a lot of is how someone should start to *feel* as they’re building self-confidence, so I was hoping you could provide some insight there. It’s one thing to notice that others are perceiving you differently in social situations, but what are some internal indications that the steps being taken are actually shifting someone’s perception of themselves?

For my part, the reason this question was prompted for me is that I realized how much more open I am about expressing my personal interests and hobbies in my current relationship. I don’t have the same “oh god what if this is too esoteric or uninteresting or nerdy” internal dialogue that I used to. I began to notice what it feels like to think that the things I’m interested in really matter, and that whatever my partner’s reaction is to them, they still have value to me. It’s hard to describe, but the feeling is similar to the sort of contagious enthusiasm I get when someone is, say, giving a speech about their area of research.

I’m assuming that confidence in other areas of life might feel a little different than what I described above, and that of course the internal state will vary from person to person, so any examples or thoughts you have would be great.

Thanks again for all you do!

Sincerely,

Possibly Moving In the General Direction of Confidence

DEAR POSSIBLY MOVING IN THE GENERAL DIRECTION OF CONFIDENCE: First and foremost, congratulations on how far you’ve come, PMIGDC! It sounds like you’re feeling much more sure of yourself and more secure and it’s great that you’re doing so well.

Confidence is one of the topics I keep coming back to, because it’s one of those topics that people tend to misunderstand. We have a lot of inaccurate and often contradictory ideas about what confidence is, what it feels like, how it works and how you get it in the first place. One of the examples that comes up the most regularly is the idea that being confidence requires success; otherwise, how could you be confident if you had nothing to be confident about?

Now, if your idea of confidence is “I have X accomplishments that say I’m great” or the knowledge that you can’t fail at Y, this would seem to make sense. How could you be confident around women if you’ve never had a relationship or even asked a woman out? How could you believe in yourself and your ability to succeed if you haven’t succeeded already? You need a reason to be confident about something, and proof that justifies it.

This quickly becomes ironic when you realize that some of the most accomplished people out there are often at their least confident when working in their field. In fact, higher levels of education and experience tend to correlate with higher levels of imposter syndrome. The people who, under this logic, have the most to be confident about are the ones who are much more inclined to believe that they don’t actually deserve their success, that their frauds and eventually people will figure it out. Meanwhile, you have folks who believe, without a doubt in their souls, that they could beat Serena Williams at tennis… despite not being pro (or even amateur) tennis players themselves.

There’s also the idea that confidence is another word for bravery; that if you’re confident about something, you don’t experience doubt or worry or anxiety about it. But that’s not it at all. Experienced singers, actors and other performers all experience stage fright or opening night nerves, even when they’re veterans of their craft. Athletes get so uptight before games that they puke or deal with other forms of gastric distress, even when they’re literal professionals. Confidence isn’t the absence of fear or worry; only the truly delusional never feel fear or nerves or get anxious. Again: knowing more and having experienced more often makes you that much more aware of what could go wrong or how things could fail.

But there’re those words again: educated. Experienced. Knowing more. Those are all part of confidence. Not in and of themselves, but as some of the building blocks that make up the holistic whole. Confidence is about belief – specifically the belief of “I’ve got this.” It’s about knowing – specifically, knowing what you’re capable of, knowing that you can succeed while also knowing that failing isn’t fatal. And it’s about experience, sure… how your experience contributes to belief, education and knowledge, in particular.

And that’s part of why you – and everyone reading this – already know what confidence feels like. You just weren’t consciously aware that it was confidence.

There are things in your life – things you do literally every day – that you are confident in. You don’t think about that feeling as confidence, because you never realized that this was what confidence is like. Confidence, you think, is something you should actively feel – a sensation in your chest or your gut that you experience in certain circumstances. But the things you feel most confident in are things that you do without thinking or feeling. You just do them, mostly without thinking, and the fact that you don’t think about it – what the implications of that action might be, what the odds of failure are, what other people might think – is part of why you don’t think of it as being confident in your abilities.

Similarly, the things that we are most confident in are things that are so mundane and universal that we don’t see the point in trying to equate those with confidence. Yay, you’re pretty good at algebra or trigonometry, that’s not confidence, that’s just 12 years of education that everyone goes through… right?

Except, no, that’s absolutely confidence. You don’t know all the answers, you can still make mistakes while you’re trying to solve the equations, but you know how to solve them and what you need to do.

Now, compare that with your being able to talk with people about your interests without worrying that you’re coming off as too weird, too esoteric or just too deep in your own head about it. To many folks that doesn’t seem like much… it’s just a conversation. But to you, that growing level of experience and knowledge – hey, you’ve done this before, it didn’t always go great but now you’re not afraid because you know you can handle it – is what you, and other people looking to be more confident have been striving for.

Just doing the thing without having to consciously think about it or worrying about your ability to do it? That’s confidence. That’s ultimately what confidence feels like: it’s something you know you’re capable of. Success isn’t assured, but failure isn’t guaranteed either, and failure doesn’t mean that it’s the end of the world. It may suck, sure… but it’s still something you can, and have experienced and have recovered from.

In many ways, confidence is ultimately freedom from worry at an existential level – you’re free to not worry, to not feel like you need to weigh every possibility, to not need to prepare for every contingency or to need to devote all of your concentration to the task. But as you gain confidence? Eventually, it isn’t a feeling. It just is.

It’s just getting to that place that gets tricky. Especially if one is still working from mistaken ideas about confidence.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com