How Do I Live A Life Less Boring?

Dear Dr. NerdLove:

I (M/26) in a reasonably large American city, and I am trying to get seriously into the dating scene. I looked around your site and your post about The Grimes Test has left me feeling down about myself since it drives home something I’ve known about myself for a while. I’ve got a place to live, I’ve got a job, I more or less have the responsible adult skills package down so I’m able to mostly handle my financial obligations. But my life is “TFW No Girlfriend” writ large.

I don’t really know how to lead up to a question like this so I’m just going to say it: I’m boring. I am dull. I am less interesting than C-SPAN reruns on a Sunday afternoon. My job is a 50 hour a week cubicle drone, my car is reliable and that’s about it. I’ve got some coworkers I get a drink with, I’ve got a couple friends post-college that I see occasionally. But there’s nothing interesting about me. My hair is ‘hair colored’ at best, my eyes are ‘yes he has some’, my body is functional and my facial features are I guess a solid C. There’s not really anything else about me to get a woman interested or inspire her to talk to me. I don’t even have anything like good “bad” tattoos or something. If I go out to the bar or the club I’m lucky if I even get served never mind get any of those signals you talk about from women. Women DEFINITELY don’t come up to talk to me unless it’s to ask to pass a napkin, and I can’t even muster up the enthusiasm to try to talk them into talking because what are we going to talk about, my mostly non-descript apartment and a used Toyota Yaris?

I guess if I wanted to be all weird internet loner I could claim I was a skilled “gray man” or whatever the fuck some TikTok video talked about but I’m not. I’m just occupying space and waiting to occupy a coffin in 60 years. How do I get to be interesting so women will actually be inspired to talk to me for more than just convenience or because I was in the way and they hadn’t noticed?

Oops I Didn’t See You There

Alright OIDSYT, let’s start off with a mistake that a lot of folks make, especially when they don’t have much dating experience. A lot of people – mostly, but hardly exclusively men – get hung up on the initial phase of meeting people and finding dates. They’ve gone all-in on the attraction phase of meeting folks; that is, they’re mostly concerned with the very beginning of the relationship. Now to be fair, this is understandable. If you’re someone who has struggled to meet amazing women, whether in person or on dating apps, just getting to the point where you’re receiving lots of (wanted) attention feels pretty significant. And honestly, most of us kinda like the idea of being someone who just rolls up and suddenly all eyes are on you; women want you, men want to be you and here you are, just able to bask in the glow of knowing you’re the focus of everyone’s interest.

But the problem is that the folks who are the most hung up on getting that attention or attraction are incredibly short sighted. They’re stuck in a pattern of short-term thinking, focused on getting over their initial hurdle of “well I don’t know how to talk to women” and “women don’t show interest in me ever” without ever thinking about what comes next. They assign all their points to try to get through the early stage without realizing that attraction means nothing if you don’t have anything to follow it up with. Hell, in some cases, they never even consider that dating or having a relationship would mean actually doing stuff that isn’t just “look over next to me and see someone pretty in the room while I do my usual routine”. So what ends up happening is that the folks who zero in on the attraction phase tend to be all sizzle and no steak.

Occasionally, there isn’t even sizzle, so much as somebody playing an MP3 of someone else’s steak cooking.

There’s a difference between being attractive, and being someone people want to date. The former doesn’t get anywhere without the latter… but the latter is what helps build the former. The key, however, is understanding how.

Thanks to capitalism and an incredibly catchy marketing campaign, we all have the image of The Most Interesting Man in the World sitting at a table at a bar or lounge, surrounded by admirers. It’s easy to think that the state of being interesting is all it takes to get there and get those results. But the fact is: there’s nothing passive about it. Being interesting and living an interesting life is the opposite of being passive.  What folks aren’t seeing is what leads to sitting at that table, surrounded by people hanging on your every word and wanting more.

(Well that and, dude, it’s a commercial. Don’t base your life off of a beverage company that just wants to sell you beer.)

Here’s what folks misunderstand about living a cool or interesting life: it requires that you put an active hand on the tiller and consciously steer your life where you want it to go. The fact that you’re boring or live a dull life is, in many ways, a choice you are making every single day. Each day you have a series of choices, and if you use those choices to do the exact same thing, then you’re never going to get out of that rut. And if those are the choices that are the easiest, most convenient or the most comfortable for you… well, that’s great, but that’s also what’s brought you to this place, where you’re not happy or satisfied.

As I’m often saying: if you want different results, you have to do things differently. And if you want to do things differently, you have to start taking direct control over your life instead of just repeating the same loop over and over on autopilot. You have to live like you actually give a damn. People who are dull or uninteresting (and unhappy about it) tend to be people who live life passively. They don’t explore, they don’t enquire, they don’t branch out. If you want a life less ordinary, then you have to spit in your palms, pick up your axe and your hammer and start building it yourself.

Now the good news is that there’s a quick and easy way to jumpstart your life to be less staid and more interesting. You have to engage your curiosity. Part of what makes people dull and uninteresting is that they are following a continuous loop, doing the same things and getting the same results. Engaging your curiosity, by necessity, breaks that loop. You always take the same route to work? Well, what happens if you go a different direction? The seemingly small act of taking a different path to the same place can open up a staggering number of opportunities – you end up seeing new neighborhoods, different stores and attractions, different restaurants, even different people. Each and every one of those is another chance to get curious and break the loop. Eat in a restaurant that you never go to because you keep defaulting back to the same old same old, and eat something that’s not typical for you. Check out some stores that aren’t just major chains, hit up attractions and points of interest that you keep passing by but never actually go into. You might vary your routine by taking a pilates group class at the gym instead of just hitting the treadmill, or join an outdoor biking group and doing some trail riding.

Another way that your curiosity can make you more interesting is to use it to learn new things. Maybe the weekend would be a good time to take classes in a new language, how to cook Indian, Mediterranean or Filipino cuisine or to learn how to dance. Or maybe you’ll go really far afield and try something that’s outside the box. A few weeks ago, I attended a knife-making workshop and learned how to use coal forges and traditional blacksmithing techniques to make a knife from a railroad spike at a living-history park. You might go in for learning lockpicking, or how to navigate with just a compass and a paper map or how to repair a vintage pinball table… skills that may not have immediate relevance or utility in your life, but you picked up just because it seemed neat.

If you can travel, then go places beyond the norm – the off-beat, the unusual, the quirky. That doesn’t mean that you have to go overseas to exotic locales, mind you. You don’t have to go to Bali or Ankhara or Petra if you want to be interesting. Even if you don’t leave the country – or your state or your county – there’re more cool, different or non-traditional places to visit and things to see. Go do the weird roadside attractions, visit the obvious tourist traps and take detours because they seem cool at the time. Hell, do some of the tourist-y shit in your own back yard; act like an out-of-towner and go do the things that you turn your nose up at because you’re a local. Collect experiences simply for the sake of having them.

Not sure where to start or where to go? Well, again, this is where taking an active hand in your life comes in. We live in a world of unprecedented access to information, and there’re more resources for finding events, restaurants, shops, classes, opportunities and hidden gems just in your hometown than you ever dreamed. Take some time, browse the local alt-weekly newspaper, sign up for Eater or HiddenCity updates, local Facebook groups and subreddits and learn about everything you have around you that you may never have even known about.

And just as importantly: talk to people. Not just folks you’re attracted to, or people you’re trying to network with, but just people. Get curious about folks, what they do, how they do it, what they think. By just being interested in folks and being open to possibilities, you dramatically increase your odds of interesting things happening. Whenever I’ve decided to just talk to folks, I’ve had some incredible experiences and met amazing individuals who had depths and surprises you could never imagine just by looking at them – treasure hunters, shipwreck divers, soap opera actresses, travel facilitators, you name it. And by having some unusual or unique or just off-beat experiences in your life or making interesting or different choices, you end up having stories to tell and knowledge to share.  That means that you are, likewise, the interesting person that other folks had the good fortune to meet.

It’s a lot easier to carry on interesting, captivating conversations when you have a broad base of general knowledge as well as a deep well of stories to share, after all.

But let’s bring things back around a bit to how this makes you more attractive and improves your dating life. And for that, we’re going to circle back to the image of The Most Interesting Man in the World. See, rememeber what I said about not seeing what lead to his being surrounded by admirers? Well, what gets him there is that by leading an active life that required talking to people, taking chances and not living a passive life. See, part of why The Most Interesting People are popular is that by doing all of those interesting things and taking all those chances, they’re building connections and networks. You know how in the movies, Indiana Jones seems to have contacts all over the world? Those happened because he actively seeks people out, focuses on getting to know people and building relationships. Interesting people are interesting in part because they’re deliberately cultivating relationships with all sorts of folks, and they’re doing so by taking the initiative, rather than waiting for Interesting Shit to happen to them. And when they build those networks and relationships, they build reputations as well. Those reputations often precede them because hey, people talk, and they love to talk about the cool people they’ve met recently.

So by the time The Most Interesting Man is at the lounge, many folks already know him. And the ones that don’t are the people he met that night and invited them over. It’s not that he showed up, sat down and waited; everything about his popularity is the result of his actively engaging with people, both that night and all the nights before. Hell, his BEING interesting was an active series of decisions, choices and intention. It was built over time through sweat, effort and perserverence.

To be sure, that’s an extreme example – and a fictional one at that. But at the same time, it serves as an example of what you could be capable of achieving if you put your mind to deliberately getting out of that loop you live in.

So as I always tell people who tell me that they fail the Grimes Test… well, what are you going to do about it? What are you willing to do to cultivate an interesting and satisfying life? Life isn’t a spectator sport. If you want an awesome life, you have to get out on the field and make it happen. If you feel like you’re boring and nobody would be interested in you, then that’s a choice. Today’s your opportunity to change that and make a different choice.

It’s all up to you.

Good luck.

Hi Doc, 

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. Thought I’d keep this short and sweet for you.

Thanks,
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.