DEAR DR. NERDLOVE: I’ve been seeing a friend of mine for 8 months now. I proposed that we start dating, which I wanted and still want, but she didn’t. During this time, we’ve ‘broken up’ a few times, always at her initiative, because she felt it wasn’t fair to me, but we always got back together shortly after.��Overall, what kept me around is that the relationship itself is basically dating. We do everything a couple does, and we don’t really hide it from our friends, so I didn’t see a reason to give up on her since everything seemed fine, despite some insecurities here and there… But in the last month, I’ve been feeling really jealous of her.��She and I have always had this thing where we flirt by teasing each other, and lately, she’s been teasing me by making me jealous, which I haven’t liked at all. It felt like she was rubbing it in my face that she could leave at any moment. I talked to her about it, and she stopped, and she’s been really nice since then. But I don’t know… Yesterday, she accidentally referred to her ex as her ‘boyfriend,’ which she corrected right away, but I’ve always felt like she hasn’t gotten over him yet. And today, when I asked if she thought about being with other people, she said no, but… ‘maybe.’ Now I don’t know if I should stay in this relationship or not. What should I do?

Half In Half Out

DEAR HALF IN HALF OUT: Here’s my question for you, HIHO: what does “dating” mean to you? What would be different from what you currently have with your fling, situationship (ugh), FWB, whatever you want to call it, if you had a different label? What, specifically, do you feel is missing, if you’re “basically” dating already?

I suspect that part of the answer is “security”. One of the things about casual relationships is that, by their nature, they tend to be tenuous and ephemeral. They can be like a soap bubble; you might be able to hold one for a little while if you’re very careful, but even the slightest twitch can make it pop. And considering how you’ve ‘broken up’ a few times (in eight months at that), I can see how that would be an issue for you.

But a label isn’t necessarily the same thing as actual security. I think the real answer is less “security” and more easing your anxiety. I’m willing to bet that the real answer would be your no longer feeling like she’s got one foot out the door and could leave at any time. And… well, I hate to tell you this, but nothing is going to fix that. Nothing external to you, anyway. What you’re feeling is anxiety and anxiety isn’t logical. That’s why we call it “anxiety”. Changing the label on your relationship isn’t going to make that go away; that’s going to have to come from within.

Here’s the thing: part of the reason why you’re experiencing anxiety over this is that you’ve made a very common mistake. You decided that you’d rather have her in this limited capacity than risk not having a relationship with her at all. But that choice comes with certain costs and one of those costs is understanding that this isn’t a “serious” relationship… and that means she may well choose to end it at any time and without warning.

(To be fair, this is true of all relationships, regardless of the label we slap on them. But again: this is part of why we call it “anxiety”.)

You, I’m guessing, feel like you’re more invested in this relationship than she is. You have more skin in the game, which makes you less likely to up and leave, but since it feels like she doesn’t, it feels like she might just up and go. That’s part of why those teasing jokes just hit the wrong way. There’s no malice behind them, but they’re poking you in a sore spot. She was teasing you like that because I suspect that she took you at your word when you said it was cool to have this FWB/situationship instead of something deeper, and thought it would be ok to joke about the nature of your relationship… in no small part because you basically told her you were cool with it. It’s good that you spoke up and said that those jokes hurt, and it’s good that she immediately cut it out… but you kind of stepped into it when you agreed to this relationship.

And while I understand your anxiety – trust me, I do – you’re not really helping yourself here. If anything, you’re making things worse when you do things like asking if she ever thinks about being with someone else. I know you’re asking for reassurance, but what you’re actually doing is trying to figure out just how close the end really is. You may not realize it… but that’s basically what you’re doing.

It’s also why you zeroed in on a very common and likely inconsequential misstatement. Her calling her ex her boyfriend isn’t some Freudian slip, it’s a neuron misfiring because he did used to be her boyfriend and that’s what she’s likely most used to referring to him as. There’s no deeper meaning there, no sign that she’s secretly still not over him, it’s just a slip of the tongue. But it’s hitting you in the brain because you’re in hypervigilance mode, trying to figure out just when the break up is going to happen and from what angle. And my guy, I hate to tell you this, but that’s really no way to feel in a relationship. Even a casual one.

That’s why I hate to say it, but I think you have to let this relationship go and accept that you can’t do something this casual. Possibly not with anyone, but especially not with her. I think that the cost of entry is going to be more than you’re willing or able to pay.

I get that you care for her. I get that you want more from this and I believe you were sincere when you agreed to settle for the kind of relationship you have now, even if it wasn’t what you wanted. I also think she genuinely cares for you. Maybe not in the way you wish she did or to the depth that you want, but still sincerely and as deeply as she can. But I think the nature of this relationship is ultimately not good for you. Some folks can compartmentalize, put aside certain feelings and accept what they have and be satisfied with it. I don’t think you’re one of those people and that’s ok. But I think that trying to be that kind of person is hurting you and I think it’s ultimately going to hurt your relationship with your friend – romantically and platonically. There’s only so long you can live in this state of hypervigilance before it starts to wear you down and grind away until you’re just raw nerves and anxiety. It’ll be better for you to be in a relationship where you aren’t constantly feeling like the Sword of Damocles is going to fall at any moment.

As much as it is going to hurt in the short term, even the medium term, I think you need to be willing to end this and move on. Take time to mourn what was and what could have been, feel all the feels about how much it sucks, and then let it go. There will be numbness and occasional shocks of pain, but the pain will stop happening so often and the numbness will fade and one day – sooner than you expect – you’ll suddenly realize that you feel ok.

And not long after that, you’ll realize you’re ready to try again. Just this time, with someone who is ready to be as invested as you are.

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 never thought your letters were true until this happened to me… 

All joking aside, I have a relationship problem that I’ve never seen anyone in the advice sphere really talk about and I’m not sure what to do about it. And before you suggest it, I’m already seeing a therapist, but this is something that has literally just happened and I’m not really sure how to process it and I think you could probably relate and give me some real insight.

The short version is: I’m an asshole and I’d like to stop being an asshole and be a better man. But I’m not sure how. 

The longer version is, well, a brief bit of backstory first. I’m what you might call a “recovering Nice Guy”, in that I spent a lot of my formative years doing the Nice Guy thing of being “friends” with a woman who I was interested in, in hopes that I could get her to fall in love with me and realize her ideal man was right there all along. Obviously that never worked out and I burned a lot of bridges along the way. Then like many incel-adjacent elder millennials with terminal Reddit poisoning I had a PUA period that came within a whisker of Andrew Tate-level f--kery. Thankfully I pulled out of that particular spiral though I will admit,  some of it got me laid. Problem is, I don’t think I was ever really sleeping with the right people. I’d be in a casual FWB relationship with someone,  sleep with them a couple times and then want to break up with them, but I’d only really fall in love rarely and never successfully. Every time I actually had feelings for someone, the relationship usually ended with me being dumped. The one that finally broke me was what I guess you could call a situationship that I initiated and thought was what I wanted. I’ll freely admit I wasn’t exactly acting my best with this person for reasons I’ll get to, but the TLDR of it all is that she had feelings for me, then I started having feelings for her and then she dumped me and it wrecked my s--t and I’ve been dealing with it for a long time now. I know it’s a form of oneitis, other women, better women etc. etc. but we’ve gotten back together very briefly but now it’s fallen apart again and it’s been doing my head in. 

Well to make a long story less long, I recently indulged in what some might call a Herculean dose of mind-altering chems with the intent of squeegeeing open my third eye and I had what others would call a stunning moment of insight where I realized exactly what my problem is: I don’t want people who want me because I feel like it’s too easy, like I almost don’t respect them, but I’m into it because I liked feeling wanted like that. 

(I know what the commentariat is going to say and I know it’s not a good look for me so please trust me when I say almost, not that I don’t and that I fully recognize and accept that this is very much a YTA situation)

On the other side, the people who run from me – metaphorically speaking – are the ones I can’t get over, and said third-eye-opening shrooms made me realize that this is because I have a tendency to almost fetishizing being the one “in control” and the ones who become my ones-that-got-away that I can’t get out of my head, like my double-ex, are ones who flipped the script on me. I was the one who was “in charge” because I cared less, then suddenly I cared and then suddenly they’re gone and I can’t seem to let that go because I fell for them and thought “Ok, I’m going to actually make this real and treat them with the respect they deserve and be my best self with them” and then as soon as I do, the relationship ends and I’m chasing them like a dog chasing cars. If the dog really wanted to date the car. 

Anyway, I’m really tired of not wanting what I have and wanting what I don’t. It doesn’t exactly take Freud to figure out how I ended up like this. I know the why of it all and I’m painfully aware of how this is the end result of my own choices, baggage and assorted assholery, but I’m not sure what to do with this newly revealed information. How do I fix this weird switch in my brain so that I can actually date someone who wants to date me without my having to go through a period of being an asshole that ultimately pushes them away because my attitude when we were dating could best be described as “Jesus that’s not healthy…”

In other words, how do I stop being so in love with being “in charge” and start bringing my real self to relationships so I don’t end up in love with someone who loved me (past tense) and then who I drive away because I was up my own ass? 

Self-Aware Self Destruct Button

DEAR SELF-AWARE SELF DESTRUCT BUTTON Alright SASDB, I’m going to give you some credit here: it seems like you’ve actually recognized and accepted your past actions for what they were, and I’m glad that it seems that you’re doing so without deflecting responsibility but also without going all “woe-is-me” and making the impact of your actions all about how you’re the worst. I hope you’ve also apologized to your ex about how you behaved, again without the performative “oh I am the worst, I am a worm, you must forgive me because I’m so pathetic” song and dance I’ve seen far too many guys do.

Not that I think it’s going to get her to give you a third try, mind you. But if you now know you treated her disrespectfully, I think it would be good for her and for you to acknowledge it and to apologize.

With that out of the way… I mean, this isn’t exactly deep or complex here. You were acting out of insecurity, and I suspect that insecurity is still at play to an extent. I also think part of the problem is how those relationships were ultimately about you, not them, and being intellectually aware of it isn’t the same as actually doing something about it. But I think the bigger, more important part of the problem is that, quite frankly, I’m not sure you’ve fully grasped what you were doing. I think you’ve got part of the picture, but without the whole picture, you’re going to make similar mistakes and end up back here with another sob story about another one who got away.

So this is going to sound like a digression, but stick with me for a second here. I think that might be helpful for you to grasp what you were doing would be to watch 500 Days of Summer, because I think this will give you some further insight to what the full issue is.

Here’s the thing: Tom, the main character in the movie, is kind of a choad, in no small part because he doesn’t really treat other people as being real. Instead, his behavior and his attitude are about how other people’s stories are ultimately about him. There’s a scene where Summer has an incredibly vulnerable moment, telling him about this recurring dream she has and what it’s meant to her. As she’s telling him, her voice fades and becomes a literal buzz in the background as Tom tunes her out and the narrator goes on about what he’s thinking. And he’s thinking, specifically, about all of this in terms of himself – how this is a sign that Summer is falling for him and how he’s getting to places where nobody has been before. Then, when she’s wrapping up the story, she says that she’d never told anyone that before… and he says “I guess I’m not just anybody”.

You can hear the f--king “achievement unlocked” sound in his voice when he says it.

And that right there is the crux of the movie and the serious flaw in Tom’s character. Someone he supposedly loves has this very vulnerable, very intimate moment, opening up to him in a way that she never has before. And not only did he stop listening, but he didn’t listen because he was too busy thinking about what this meant for him. And then when she underlines just how big of a deal this is for her… he makes the moment about him. Not “wow, thank you for sharing that”, not engaging with what it means for her, he sees it in how this moment affirms his specialness and his status as the Main Character Of The Universe.  

That’s more or less what you’d been doing. I mean,  you said it yourself: you don’t need to be Freud to see how all of this stems from your need to feel Important after however many years of feeling insignificant or undeserving or otherwise unworthy. The whole Nice Guy schtick that guys pull (and I’m very much including myself in that) comes from feeling too un-self-confident to actually own your interest and unwilling to risk outright rejection. So instead, they play games in hopes of being able to get what they want without ever actually taking a risk or making themselves vulnerable to another person. And that works out about as well as you might think.

(And, again, speaking from experience here, if it does work, that’s usually a sign that you need to run like all of hell and half of Hoboken was after you.)

Then later on, you learned some tricks and had some success and it plays to your ego and makes you feel like The Specialist of Special Boys, and you like the feeling of power it gives. Because it is power – it’s the power of not caring, the power of being able to put on an act without actually risking investment and still getting what you want. Even if what you want ultimately ends up being hollow and unsatisfying because you’re treating it like a game and oh look, the points don’t actually matter.

But when you start feeling actual feelings, instead of grooving on the power of caring less – about the relationship, about the other person – and how much they care about you, then s--t falls apart all over again. Because now you have actual skin in the game. Now you can actually be hurt. And, quite bluntly, realizing “oh, now I actually care about you” after you’ve been aloof and distant and enjoying the head games is frankly insulting to the person you claim to care about.

You wanted to feel special and thought that you were doing just enough to keep the other person around and didn’t realize the hurt it caused, in part because… well, it was always about you. And once it wasn’t about you (…ok wasn’t about you-ish), it only came about after you had been treating the other person like an accessory, not a person.

This is one of the reasons why the biggest sin of a casual relationship is to treat the other person casually. It’s not exactly a surprise when someone doesn’t feel like they can trust you or be vulnerable with you when you’ve done this, even after you supposedly repented, seen the light and made a switch.

And while you can do your best to say “but baby, I’ve changed!”, you’re going to have a hard time convincing people because some hurts run pretty deep and anyone can say some s--t. As the saying goes: deeds, not words. You are going to have to prove you walk the walk as much as you talk the talk.

So how do you flip the switch now that you know this about yourself? Well… you’re going to have to start letting go of the detachment you were holding onto. In fact, congratulations, I’m going to make a recommendation I’ve never made before: I think  you should be ruling out casual relationships or “situationships” (GOD I hate that term) because it’s pretty clear you were using them as a crutch to prop up your ego rather than an honest assessment of what you had to offer or what kind of relationship you could reasonably maintain.

I think, if you’re going to date someone going forward, you’re going to have to do what you haven’t done and actually date intentionally, pursuing relationships with people you can actually be serious with. You’ve gotten too comfortable holding yourself apart from people you were dating and it became a habit. So I think you need to unlearn that habit and the way to do that is to consciously do what you’ve avoided doing before now: be real, be vulnerable and be present with the people you date. You are going to have to consciously let go of the idea of having “control” or being “in charge”, no matter how much zing it puts in your spring, and be willing to get messy and confused like the rest of us. You have to stop being detached and be there, be in the moment and consciously give your time and attention to the person you’re dating.

Maybe after you’ve done this for a while and you can get over that need to prove that you’re “special” – to yourself, to the universe, to whomever you think you need to prove this s--t to – you can date casually again. But for now? You need to pull your head out of your ass and put your whole self into your relationships. It may mean you’re going to get hurt more. It may mean that you’re going to date less. But this way, at least, when you do date people, it’ll be meaningful for you and for them instead of someone trying to forge something serious with a person who doesn’t take them seriously.

And to be clear: I think you’re coming to this from a place of honesty and integrity. I do think you’re sincere about this, and I think it speaks well of you that you’ve recognized this about yourself and you’re willing to own it. If it sounds like I’m getting especially heated on the topic, it’s because I know of which I speak. I have been there, done that and blown up good things because of it. So here I am, speaking to you as the voice of experience: you f--ked up a good thing because you wanted to feel good about yourself and didn’t think about how it made other people feel.

It’s time to put this newfound self-awareness into practice, stop holding yourself back and get down in the muck with the people you want to care for. It’s time to stop trying to be casual and get back to the boy you used to be – who felt deeply, but didn’t have the courage at the time to act on those feelings. We always say “if I knew then what I know now”. Well, now you know. And while knowing may be half the battle, the other half is actually doing it.

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: 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.

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