Do I Need To Fix My Life Before I Bother Trying to Date?

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Do I Need To Fix My Life Before I Bother Trying to Date?

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Estimated reading time: 14 minutes

Hello Doctor, first time, long time. Very, very long time. I am writing in because I want to date. Bad. However, I feel like I am not in a place to do so. HOWEVER, I also feel like the reason I’m not in a place to do so is because I’m not doing so. Let me explain.

I only have a little over a year left of my twenties. Regretfully, I haven’t done much of anything with the time. I went to (community) college, made one friend who I still talk to (text) to this day. I got a job that I’ve now been at for seven years. I hate it! Ignoring a quarterly bonus, I bring home about $2,000 a month, and that number isn’t going up anytime soon. I made one long-lasting friend there who I talk to when I can, sometimes that takes months. He’s busy – married, kid, demanding job, I can’t blame him and I won’t pester him.

I have hobbies, but nothing particularly social. I’ve been collecting my whole life, a good bit of Lego, got into Gundam models more recently, and the most recent Pokémon games have reignited my love for that franchise. I have recently been trying to get back into the tcg, which is tough because I don’t know of any local groups that get together just for the sake of playing and hanging out. I watch some movies, some anime, some videogames, all single player, and recently decided I would start to learn Japanese. It’s going very slowly, all of it, because I have been seriously lacking the energy or motivation to keep up with my games, movies, shows and Japanese.

I live at home. It’s a double-edged sword. On one hand, I have been able to save up a truly embarrassing amount of money, which I’m very proud of, for somebody living at home (well into five figures). I needed a new car early last year, which I was able to afford out of pocket, but still got a sizable amount of help from my parents, thus allowing my savings to not plummet to near zero. My current job, while being trash and a dead end, allows me to just, kind of buy what I want. I do put limits on myself however, I always make sure I’m not dipping below where I was the previous month. I pay my own car insurance, I pay taxes, I’m self-sufficient, and whenever I’m told to pay up for something extra, I do so.

I’m not the only child still living here, and out of respect for them, I’ll leave it at that. My parents are starting to get up there in age as well, and while they’ve told me otherwise, I can’t help but feel like I’m taking advantage of them at this point. The house is cramped, and while I’ve taken big steps to limit my collectables/clothes/shit to just my room, that isn’t the case for anyone else. I want to live on my own, that sounds great, I could be proud of that, but I’d also be lying to you if I said I was actively looking, or excited by the realities of paying an obscene amount of money on rent for a place I’ll never own. I would never want to bring a date here.

My job is dead to me. I started when I was 21, I was one of the newest employees for a very long time. Aside from five other employees, I’m now the oldest. Seven years, after taxes and health insurance are taken out, I make $500 a week, rounded. It’s a retail job; I never loved it, but when I was younger, I thought, if I need to make something out of this, I could. That illusion is gone. I clearly don’t want to be there, I don’t talk to anyone, I do my job, get the shit done and do it well. They keep me around because I’m needed. And while they need me, I know they won’t give me a position with any serious raise- not that I would want it anyway. It’s a thankless job and it’s been a real drain on me physically and mentally. I’m currently using apps to look for new work, but nothing good has come up, not yet at least.

The thing that finally got me out of this misery was when I attended my first social event in too long, a couple weeks ago. Despite it getting cut short abruptly due to having to evacuate the building for reasons not relevant to this event, I really enjoyed myself. Nervous at first, but once things settled down and I started talking to people, I found I was actually pretty confident and happy with how things were going. I was happy! Talking to people! Probably around my age! This was a very off the cuff decision, made less than a week in advance and due to being cut short, I didn’t get any names or numbers.

So here’s the thing, Doc, I have been pretty damn lonely for a long time now. Never had a relationship, would like to actually start to date. The only experience I’ve ever had was a few dates with a coworker six years ago, which I cut off once she wanted to get more serious. I liked her but I had my reasons for doing so, and I know I made the right call in hindsight. With a lack of real friend groups to meet new people with, I have been toying with the idea of dating apps, Bumble caught my eye in particular. Now, in spite of everything I just wrote, I know I’m still ALLOWED to date and find a good relationship. I’m not convinced of my own perpetual suffering. But I also know that the things I want to change aren’t going to change overnight and I’m tired of feeling like they’re things I need to fix before I even try to put myself out there. I feel like doing the dating thing could be a very good thing for me! I’m not looking for the o n e lady who will make it all better, I’m looking for someone who is around my age that I can have a genuine connection with and am eager to just spend time with, wherever we are in life. Just, how do I navigate trying to date while living at home, in my weird position, still living in the same four walls that I grew up in, surrounded by collectibles? I don’t feel like I’ve truly lived a life yet, and sometimes I know the best way for me to break out of a slump is to say fuck it and jump in the deep end.

Thanks for whatever you write to me in advance, Doc.

Stuck In Neutral

I’m going to go ahead and guess that this is one of those letters that’s more asking for permission than actual advice, SIN, because you already say you know what you need to do.

Well… yeah. You’re right. You do. So maybe the better question is to ask yourself why you’re not doing it yet.

Now, part of the problem you’re running into is what’s known as “the opportunity cost” – that is, you’re dealing with a series of finite resources (in this case, time, emotional bandwidth and personal energy) and quite literally everything you do requires using at least one of those resources. And yes, I mean everything. Sleeping, eating, work… these all come with opportunity costs. This means that you have to budget out what you want to do, what it’s going to cost you to do them (the opportunity cost) and whether you have the available resources to actually accomplish those things.

And since these are all finite resources that don’t get replenished or carried over – you don’t get extra hours to use on the next day if you go to bed early, after all – it means that anything you want to do is going to come at the expense of something that you’re already doing. Want to hit the gym more but can’t adjust your work schedule? Ok… well, getting up early is the opportunity cost, taking resources (time) away from another activity (sleeping).

You’re already encountering this – you don’t really have the energy to give to most of the things you want to do. That’s going to make it really difficult to do some of the other things you want… things that are going to take quite a bit more time and energy and bandwidth than you currently have to spare. 

It’s also important to note that you’ve already made certain decisions that lead you to where you are now. You’ve prioritized most of your current lifestyle – which clearly hasn’t made you happy or left you feeling at least satisfied in a while – over making changes. And to be clear, I’m not presenting this as judgment over your choices. It’s just important to recognize that they were choices… even if you didn’t realize it at the time.

You could, for example, have stopped putting so much time into playing video games or watching movies, and taken that time and energy to go out and meet new people. Similarly, you could’ve been taking that time to look for another job or a place to live – either on your own or with roommates. You decided that those were just not a priority for you.

Again, I’m not saying this to be judgmental or to say that you wasted time or made the wrong choices. You, presumably, were getting something from those activities that you felt were more important or giving you a greater reward than trying to chase these other goals. This is entirely reasonable! You’re allowed to say “ok, right now, this thing is more important to me than these other things I may also want”.  

Now you feel differently, so it’s time to make different choices.

So part of what you’re going to need to do as part of breaking out of your slump is to take a long, hard look at your day to day life, the things you’re doing now and look at the things that you want to do… and then figure out what you’re going to give up in order to free up the resources to do those things.  

Want to meet new friends and build a social network? OK… well, that’s going to come at the expense of something else. Want to date? Same story. Find a different job? Ditto. Sometimes you can blend two goals together – building your social circle makes it easier to meet potential dates, after all – but it’s still going to require time and energy.

It may help to stop and take an honest appraisal of some of your current hobbies or interests. How many of them are still rewarding to you and how many of them are you participating in out of a sense of obligation or “I’ve been doing it for X long now, I can’t just stop.” Sometimes, we hold onto things because we feel like we have to, rather than because they actually bring joy or value to our lives. This may be a good time to take stock and see if you’re holding onto things out of habit rather than an actual desire.

It’s also important to realize that the changes don’t need to be “finished” before you are “allowed” to date. That mindset quickly becomes a way of avoiding changes or taking on other opportunities. People with dead end jobs date and have relationships. So do people who live in multi-generational households (which is more than 50% of Gen Z and nearly a quarter of Millennials). You would hardly be seen as being unusual for  any these circumstances; the only person who cares as much as you fear is, well… you.

But again: it’s going to require that you free up time, energy and emotional bandwidth to do so. So you’re going to have to give something – likely several somethings – to do so. So you’re going to have to decide where your priorities lie and what order you’re going to attack this to-do list in.

Once you decide what’s important to you ­– or more important than other things – you’ll have a much better idea of where to start. But you still have to start. Otherwise, you’re going to spend another year, no closer to the goals you presumably want. Like the sage says:

No such thing as spare time, no such thing as free time
No such thing as down time
All you got is life time… go

Good luck.


Dear Dr. NerdLove:

I was talking to a group of female friends the other week, and it got onto the subject of dating and relationships. When the conversation turned to discussing my experiences, I told them the truth – that I hadn’t dated in many years, and that women don’t seem to have much interest in me. This was something of a shock to them, and it led to a good few minutes of me being told that I am very handsome, that I’m really good at making women laugh, that I make them feel comfortable (which is a nice comment to receive, honestly…) and such like. I’ve had this conversation many times before, to no avail, so I ended it as soon as I could.

Throughout adulthood, I’ve had many moments like the above, and I’ve received a lot of compliments from people regarding my appearance and personality. It’s been pretty consistent since my early twenties, and has only gotten more regular over time. I’ve had everything from people just assuming I have a partner, to thinking that I’m sleeping with people from my friendship group or at work. It’s not just the biased impressions of friends either – I’ve had people approach me at nightclubs, or in the street, to offer similar compliments. I just don’t understand why they think this. I’d like to think I’ve got a lot going for me, but the reality is I’m just an average guy, and I’m certainly not at my peak (for example, I’ve had to move back home to save money).

And the other matter, as mentioned before, is that women don’t show even the slightest hint of interest. I’ve noticed throughout my life that women within my age range, and of a certain “attractiveness”, don’t even acknowledge my existence, and the remaining choices are out-of-bounds, for one reason or another. My career is dominated by married, older women, so that’s a no-go. My hobbies are female dominated, but beyond platonic interactions, there’s nothing of note there. And on the rare occasion that I do go out to party, there’s no eye-contact from across the dance floor.

Yet everyone thinks I’m a womanizer, and they’ve even used that exact term. “You could get any girl you wanted”, “You have loads of options”. Urgh! It hurts, honestly, because I would have loved to have met someone special by now, or at the very least have some experience with relationships or a few casual encounters. As it stands, the last time I went on a date was when I was twenty years old.

I’m no closer to understanding why people think this of me, and certainly no closer to changing my circumstances. Any advice on this one, Doc?

Who Do You Think I Am?

You know, WDYTIA, I’m going to do something I don’t do very often: I’m gonna get a little inside baseball. I chose your letter not because it’s an especially insightful or unique question but because it’s an illustration of something that comes up a lot. And in examining this, I think you’ll glean some important insight into your issues if you take a second and actually apply it.

Humans, as a species, derive a lot of conclusions based on incomplete information. Our brains are almost custom-designed for it. After all, seeing patterns and recognizing recurring issues, even if you don’t understand everything about it, is pretty important for survival. If Throg and Zazz and Gary all eat similar looking red berries that come from similar looking plants, and all of them get sick and die, we can make a reasonable inference that hey, maybe eating those berries is a bad fucking idea.

The problem is, however, that making inferences off relatively little information doesn’t mean that we’re always coming to the correct conclusions. This is especially true when you start getting into intellectual blind spots. While we may be making inferences and drawing conclusions based around what we’re observing, that doesn’t mean that we’re doing so out of pure deductive reasoning and logic. We’re frequently letting our biases, suppositions and preconceived notions inform those observations and conclusions. If someone watches Thag and Zazz die from eating red berries, they may decide the issue isn’t the berry but the color red, for example.

The same comes from making judgements about other people. Your friends are working from relatively limited information – how you look and act when you’re around them. They’re drawing inferences from that information based partially on their own experiences but also on their own cognitive biases and beliefs. So they see you and the qualities you have and make assumptions based on the information they have, while bolstered by their beliefs. And since they don’t have a 24/7 live feed of your entire life… well, they’re drawing incorrect conclusions based off of limited information.

Funny thing though… you’re doing the same thing. You’re making a lot of assumptions of the people around you, based on limited and unreliable information and a whole lot of biases and beliefs coloring what you’re seeing. Your beliefs about yourself are affecting what you’re seeing and – critically – what you’re not seeing and how you interpret all that information.

So an important question to ask yourself would be: if your friends, who presumably are intelligent and observant individuals could be so very wrong about what they think of you… maybe, just maybe you are also wrong about what you think you’re seeing (or not) when you’re dealing with women. And maybe your friends are seeing something in you that you don’t because you refuse to believe it about yourself. 

So, if we assume that your friends — and those strangers coming up to tell you similar things — aren’t just stroking your ego, maybe this is your opportunity to try pushing back against those self-limiting beliefs, challenging them and addressing the serious possibility that you were entirely wrong about them. 

And while you’re doing that, it may be the right time to experiment a bit, test that hypothesis and see if you’ve got more appeal than you give yourself credit for. In fact, a solid test would be to start actually making moves and talking to those sexy someones you’ve been seeing, instead of coming up with reasons to believe that you’re not desirable or interesting to anyone.

Y’know. For science.

Good luck.

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