I (28M) wonder how I can stop second guessing myself in dating. Everything seems to be going right. Yet, I wonder: is it? When do I know that I’ve become successful at dating?
As background, I’ve only been dating for a year, when, after the pandemic, I started thinking, “maybe I should find a wife.” Since then, I’ve had a lot of first dates and some second ones. I’ve never been in a relationship and never had a girlfriend.
I took that internet test that uses personality to predict gender and, based on my answers, it predicted that I have a 98 percent chance of being a woman. While I’m secure in my manhood, I think that does sum up who I am as a person. I have a lot of stereotypically feminine traits. And when I read advice blogs, I’m almost always taking the (typical) woman’s perspective. So, my approach to dating seems, from what I read, like a typical woman’s.
And I only ever date exactly one kind of woman: shy, religious, nerdy, practical ones. Around my age. Who all look somewhat similar. I simply am incapable of dating anyone else. Everything about how I date attracts this kind of woman: how I talk, what I talk about, who I am, everything. I’m somehow very good at attracting this particular kind of woman and no other kinds.
So, every woman who I have a conversation with on a dating app is like that. Even if it’s not obvious from their profile. Every woman who I am interested in in real-life is like that. I’ve only been on multiple dates with about five women in my life, and they were (almost) all like that.
Sometimes, I wonder what it would be like to meet a woman at a bar. Except I never go to bars. And I never drink. I just think maybe this is my last moment to potentially become an “exciting, cool person.” And while I know it’s bad to date someone just because they will improve who you are. I sort of feel like if only I dated someone “cool and exciting”, maybe I could become that way. And I would have lots of fun.
Or if I date my type, maybe I’ll lose some essential part of myself, like I’ll switch from being an extrovert to being an introvert. Or something else bad, given I’ve never had a girlfriend, I would not know.
I did date exactly one woman who was different from my type, ever so slightly. She was very extroverted and had a chaotic energy. That ended after two dates. I felt super anxious when dating her. I suppose I didn’t really feel like we had much going for us. And maybe it was a self-fulfilling prophecy. She said we didn’t have chemistry after two dates.
And right now, I’ve been on multiple dates with a woman who’s exactly my type. And more or less, exactly like everyone I date. We’re taking our relationship very slowly. I don’t feel that anxious. Yet, I don’t feel that excited either. Maybe I just need to wait a month or so for “new relationship energy.” I simply wonder if I actually like her or I just like her, because of who she is, that she has all the attributes of my type (for example, she reads a lot, she plays board games).
How do I know if I actually want to be in a relationship with a woman who’s my type? How do I know if me and women of this type would actually make for a good relationship? Or how do I know if I simply am physically and emotionally incapable of dating anyone else?
Before we get to your letter, I have a quick comment. I realize there’s a certain amount of irony in this coming from someone who makes his living as a Very Online loudmouth, Confused, but have you considered that maybe you shouldn’t base your self-identity around quizzes and random things you’ve read on the Internet? While I love me a good time-waster and have probably given up far too much information to D&D character class/alignment quizzes, those really aren’t a basis for… well, anything important, really.
But that’s secondary to the issue at hand here. The issue you’re having is less about your type so much as it is about what you’re comfortable with. There’s a pretty significant difference between the two. There’re the folks you’re attracted to and would prefer to date, and then there are the folks you’re used to. Sometimes these line up. Sometimes they don’t. Things get problematic when the latter ends up overriding the former, especially when you treat this as some sort of mandate from Heaven.
Here’s the thing, Confused: you’ve spent most of your life surrounded by the people you describe: shy, religious, nerdy and practical. They are a known quantity. You’re comfortable with them because you know where you stand, you know what they’re like as people and you know what to expect. It’s easier because, well, they’re not a challenge for you. They don’t push you outside of your comfort zone, nor does dating them or interacting with them challenge your self-identity. They are, quite frankly, safe.
Now this, in and of itself, isn’t a bad thing. Shy, religious, practical and nerdy women are just as awesome as outgoing, extroverted chaos agents. The problem, however, is that it doesn’t seem like you are attracted to them. They’re easy for you to talk to and interact with, but they don’t excite you or interest you or make you feel like punching the air and yelling for joy. And therein lies the issue.
If we look at the woman you’re currently seeing, that pattern is continuing. You’ve been on several dates with this new woman. It’s been easy. It’s been stress free. And, apparently, it’s been less than thrilling. Unless you already know yourself to be some flavor of asexual or demisexual — which is certainly possible — then you’re likely not actually into her, romantically or sexually. New relationship energy isn’t something that kicks in after a month for most folks; it’s something that comes up pretty quickly when you’re dating someone you’re into. Part of what makes the early days of dating somebody fun is that initial excitement, wanting to see them, spend time with them and the thrill of their touch, their kiss, even their scent. If you’re not feeling much for her besides “it’s comfortable” after several dates, I think you can safely say that you’re not into her.
And if this is the same experience you have with the other women who are “your type”, that’s a pretty good indication that your type isn’t.
But I suspect this is less about “types” so much as it is about something deeper and more personal. This isn’t to say that your issue is that you’re dating the wrong women or that your type isn’t your type. I suspect this isn’t about the women you date, but about how you feel about yourself.
The issue at hand seems to be that you think this is what you’re limited to because of who you are… and you seem dissatisfied with the “who you are” part. Folks who are happy and satisfied with themselves don’t tend to worry, say, that they’re about to miss the window of opportunity to “become an exciting, cool person.” Don’t get me wrong: this doesn’t mean that being steady, reliable and possibly a little square is bad or undesirable. Some folks are hobbits, who prefer quiet, unobtrusive lives. Some folks are dwarves — industrious rise-and-grind types, while others are the more academic elves. Still others are the more mercurial humans who have more of an appetite for excitement and adventure.
None of these are inherently better or worse than the others. Each of these (highly oversimplified) types all have their advantages and disadvantages. Samwise Gamgee isn’t exciting, per se — he’s solid, practical and down-to-earth — but he’s a valued friend and member of The Fellowship and husband-goals for a lot of women out there. But there’re some folks out there who think they’re supposed to be hobbits when they’re not. The problem is that trying to live as that type of person doesn’t make them happy.
And hey, that happens a lot. Sometimes the role or community you’re born into isn’t necessarily a good fit for you. And this is true amongst every type — hobbits, dwarves, humans, elves, etc. You’ve got variations in every group; Bilbo discovered he had an affection for travel and adventure, Gimli became a friend of the elves in general and had a connection with Galadriel specifically and so on. But the key here is that if your type isn’t a good fit, then it’s on you to try exploring others.
Case in point: you talk about wanting to be more exciting and cool. You wonder what it would be like to meet women at bars. Well, leaving aside that meeting women in bars isn’t the end-all/be-all experience some folks think it is… what have you done about it? Have you made a point of getting out of your comfort zone? Have you attempted doing things that would be “out of character” for you — not just once, but enough times to gauge the difference between “I’m uncomfortable with this because it’s new to me” and “I’m uncomfortable with this because it’s not right for me”?
An obvious example would be the woman went on a couple of dates with. Part of why you were anxious was because this was unfamiliar to you. You felt like this was some sort of test or trial, with rewards and consequences, and you were afraid of getting it “wrong”. With your usual “type”, you knew what to expect and — more importantly — you were able to coast on autopilot. Yes, you and this woman didn’t have chemistry, but that’s not solely down to her being different. You can meet folks who are exactly the sorts of folks you’re compatible with and still not have chemistry with them. Declaring it a one-and-done experiment belies the fact that this was the first time you stepped out of your comfort zone and — surprise surprise — it wasn’t comfortable… yet. And that yet is important because everything unfamiliar tends to be uncomfortable to one degree or another at first. You’re trying to figure out what to expect and how to act! But with time, practice and experience, you learn.
That’s something you can apply to those other aspects in your life — including “well, I wonder what it would be like if…” parts. The “meeting women in bars” part is the easiest thing in the world to try; put on your traveling feet, hop over to Bree and see what the action’s like at The Prancing Pony. You don’t need to become a barfly and/or drink yourself stupid to see if that’s something you enjoy. Hell, you can go to bars and not drink alcohol at all. I promise you, not only will most people not notice or care if you’re having a Coke instead of a beer, stick a lime on a glass of soda water and everyone will assume you’re just having a cocktail.
However those are details, not the core of the issue. The most important issue isn’t trying on different roles or experimenting with different choices, it’s that you have to do it for yourself. Not because of the person you’re dating, but because you want to expand your horizons and see if you’ve been defining yourself by false limitations.
The thing is, you seem to have convinced yourself that women and relationships have transformative properties; that if you were to date someone with the right qualities, you would adopt those qualities yourself. This is very much out of the Manic Pixie Dream Girl fantasy: that some quirky, outgoing and unusual woman will see the untapped potential in a dude who’s stuck in his ways and teach him how to lighten up via quirky dates plus blowjobs. That doesn’t happen. Leaving aside that MPDGs don’t exist, women in general aren’t looking to teach dudes important and transformative life-lessons. All this fantasy does is move the responsibility for managing your own life onto someone else. Relationships don’t change you into a different person — certainly not permanently. More often than not, the folks who hope that a particular “type” will change them are into that type because they’re seeing that lack in themselves. But expecting someone to fill that lack for you is a fool’s errand.
Nobody can make it happen for you. You have to choose it and pursue it on your own.
How do you know if your type is right for you? How do you know if you’re capable of dating other people? That’s easy: you date other people. You push yourself out of your comfort zone, try connecting with folks who aren’t your usual type and see what happens. Again: you don’t want to do this once and call it a day if it doesn’t go perfectly. You want to give this a genuine shot.
But before you do that? I suggest you get out and start pushing the envelope of “who you are”. Consider those personality traits you wish you had — being “cool” or “exciting”. What does that look like? How would that person act? How would they dress? What would your life be like if you were that person. Take the answers to those questions and then start applying them to your life. Not “down the line” or “when you’ve done X, Y or Z” but right now. You don’t need to wait to start trying to be more exciting until you’ve hit some developmental milestone; you can start now. Today.
I’m not going to tell you to stop seeing the woman you’re currently seeing, though I will tell you not to commit to anything yet. What I am telling you to do is to look at your life, look at who you wish you were more like and start to model that behavior. Instead of focusing on your type, focus on yourself first. Take a few steps outside of your comfort zone and give living that different life a shot. Try it on for size, see how it feels past that initial pain point and then see how much your interest in your “type” has changed. You may discover that yes, you are more into the more outgoing, slightly wilder type. Or you may get confirmation that yes, you are a hobbit and that’s exactly what you’re looking for.
But that can’t happen until you decide to make it happen.
It’s in your hands, Confused. Time for you to take a giant step outside your mind and see.
I’ve been reading your advice for a while and I always enjoy it.
Anyway, to the matter at hand.
I’ve been with my current boyfriend just over 2 1/2 years and I love him dearly. We enjoy a lot of the same things and he treats me with the utmost respect. He’s my biggest cheerleader in life and I truly don’t know what I’ve done to deserve him.
That being said, I’m currently enjoying a low point in my life. I feel like I’ve hit my absolute rock bottom and this is the lowest I’ve ever been, and I’m longing for something new. I feel like my life needs a shot of rejuvenation and a fresh start.
I have ZERO idea how to go about this. No matter how I word it, he’s gonna take it personally and I’m gonna end up being the bad guy. Another reason why this is giving me anxiety is because I’m TERRIFIED of starting over. Not to mention dating as a whole is kinda miserable anyway, but doing it as a gay man in a small town is even worse.
I’d love some suggestions about how you think I should go about this.
Rocky Bottom Blues
There’s an Alex Norris comic I’ve seen on Facebook and Twitter, RBB; maybe you’ve seen it too. It features a pink, abstract blob of a character, looking at their room and saying “I want things to be different”. Then after smashing things and spreading chaos around their room, they look around and say “oh no”. The implication being that yes, they got their wish… and that made things worse.
I bring this up because, frankly, I’ve seen a lot of folks who get a desire for things to be different and think that “different” means “destroying everything I have now”. In trying to make changes or make things different, they change the wrong things. Rather than figuring out exactly what the issue is, they take a scorched earth approach and burn everything down around them — the better to start over from scratch. The problem is… in tearing everything down, they quickly realize that the answer wasn’t “things need to be different” and they’ve often lost things that they cared about or that were important to them.
That, honestly, is a somewhat long-winded way of saying “are you sure you want to do this?” You have a boyfriend that you love, who makes you happy, who treats you well and brings good things to your life. So why, exactly, do you feel that you need to give that up?
That’s not an idle question, by the way. I’m sincerely asking. You say that you’re at a low point in your life — the lowest you’ve ever been — and that you’re looking for something new. Ok, I get that. But what does that mean, exactly? Are you stuck in a rut? Does this mean that you feel as though you’re not making progress towards your goals and ambitions? Are you feeling like you’ve reached the limits of what you can achieve in this particular place at this particular time? Or is it that you want out of this relationship and you can’t bring yourself to admit that?
A lot of times, when folks decide they want out, they don’t like to face the fact that they’ve just decided that they’re done. A lot of people feel as though they need to have a reason to leave that they can point to, some causus belli that justifies a break-up to themselves and to others. If they don’t have one, they’ll often invent one. Sometimes they’ll slam their hand down on the Relationship Self Destruct button and cheat in ways that ultimately get them caught. Other times, they’ll look to other reasons to rationalize the break-up… such as, say, deciding they need to shake things up and start over.
The thing is, in a some of cases, this is less a “needing a reason to motivate themselves to leave” and more of a face-saving measure. They want to break up because they want to fuck other people or because they’re no longer attracted to or love their partner… but they know that admitting this can make them look like The Asshole to others. So having that external cause becomes a way to justify doing what they already wanted to do, without having to take responsibility for it. It couldn’t be helped, this just had to happen, ah the tragic fate of star-crossed lovers, oh well, life goes on.
And while I totally understand not wanting to come off like the bad guy in the break-up, it’s better to have the integrity of owning your desire to be single again. Does it make you selfish? Yeah… a little. But selfish isn’t automatically bad. It may suck in the short term, but it’s better in the long term. I mean, how do you think your boyfriend would feel if you stayed until you had a “legitimate” reason to leave, only to discover that you’d been quietly dying inside the entire time? Wouldn’t that initial selfishness be better in the long run if it meant that you were freeing your boyfriend to find someone who did want to be in that relationship with them, instead of spending that time with someone who doesn’t?
However, that’s not the only possibility here. There’s also the possibility that what you’re feeling is transitory and will change sooner rather than later. In that case, you run the risk of making semi-permanent changes because of a temporary situation. A lot of folks have thought that they needed to shake up their lives and be free again, only to realize that they didn’t need to throw everything out in their eagerness for change. It would be a shame to give up an otherwise happy relationship that doesn’t need to end just yet.
You may notice that I haven’t exactly come down on “yes, end this” or “no, you should stay”; that’s because of that lack of information. Without knowing more about what your situation is, it’s hard for me to tell you whether breaking up with your boyfriend is the right move or the wrong one. Before you decide to start over as a gay man in a small town, you should see if you can pinpoint what is causing this malaise and why. The more you understand the root cause, the more you’ll know about how to proceed and what the best option would be. Maybe there’s a way you could have both the changes that rejuvenate your life and the boyfriend that you love and who treats you well.
Or maybe the relationship has reached its end point for you. The only reason you “need” to break up with someone is that you want to break up with them. If that’s the case… well, then the best thing would be to break up. And yes, there is no way of wording things that’s going to make this not hurt or not make you look like the asshole in the short term. Unless you and he both recognize that your time together has come to its natural conclusion, break-ups tend to be one-sided affairs, and being told “I don’t want to be with you anymore” hurts. But as the saying goes: pain is inevitable; suffering is optional.
In that case, the best thing you can do is avoid causing unnecessary pain. If you’ve decided that breaking up with your boyfriend needs to happen, then it’s better to do it as quickly as possible. The clean break heals the fastest and the short, sharp pain fades the quickest. Dragging it out makes things worse and risks damaging any future relationship the two of you may ever have together. The process of breaking up works best when it’s accomplished in as fast and efficiently as you can manage; the lingering issues of, say, continuing to live together in the aftermath can make things hurt even more. So if you’re going to break up with him, have the conversation with him on the same day that you sever ties, rather than prolonging things. Tell him that you’re ending things and that it’s not because of anything he’s done. Let him know that he has done everything right and he’s amazing and treated you like a king and that you treasure the time you’ve had with him; it’s just that your time together has ended for you and you need to go. Don’t drag it out, don’t let it turn into a negotiation or otherwise buy time before you have the conversation again. Let it be a swift, sharp pain and then let it be over so he can heal.
If you want to help give him a softer place to land, then let your mutual friends know that it’s happening and that he’s going to need comfort and care; this way, you’re not leaving him to sit with this alone. At the very least, he’ll have folks who care for him to support him in the early days after you leave. Just because you’re ending things doesn’t mean that you can’t still do something kind and loving for him.
But as I said: before you make any decisions, make sure you understand how you’re feeling and why. It’s a lot harder to take back a break up if you realize you made a mistake than it is to say “Ok, I need to do X, Y and Z things differently.”