DEAR DR. NERDLOVE: So, I recently decided to make things official with a girl I first dated in the fall of 2023 but ended things with because it didn’t seem like we were right for each other. We had a lot in common as people, so we stayed in touch, but we both dated other people until almost exactly a year later, when coincidentally we both broke up with the people we were with. We met up again, things clicked and five months later we decided we should be exclusive.

The problem is that she will not let go of the fact that, in her mind, I ditched her for the woman I was dating for that year – even though she dated multiple other guys between then and when we got back in contact. She also obsesses over her idea that this woman was so much “hotter” than her, which isn’t even true. I’ve had many, many conversations with her and explained everything honestly. But it just won’t stop. I never know when I’m going to say or do something that in her mind will trigger an outburst about an ex who at this point has been out of the picture for half a year and who I definitely don’t miss or ever directly talk about. She’s even gone to therapy for the issue but it doesn’t seem to have helped her.

She’s a great person for me and our interactions are usually fantastic – except this problem keeps cropping up. What’s my move?

We Were On A Break

DEAR WE WERE ON A BREAK: You know, I get a lot of letters from people with what I call “the Sir Mix-A-Lot problem”  – “everything about our relationship is great…” and then someone calls 1-900-Mix-A-Lot because there’s a big ol’ BUT heading straight for them.

Most of the time, I hear from women who have these relationships, so it’s a little perversely refreshing to have it coming from a man.

I’ll be honest, WWOAB, I wish you mentioned what the circumstances of your breakup were beyond “we didn’t seem right for each other” – whether the breakup was mutual or not, who initiated it and so on. This isn’t going to be relevant to who’s in the right or who’s justified here, so much as how it may give a little insight to where your girlfriend’s head is at.

It’s certainly possible that, if you were the one who initiated the conversation and were also the one to date someone else first after you two broke up, that she feels slighted or that the speed with which you met this person is sus. It also sounds like this was the only person you dated between breaking up and getting back together, while she at least went on dates with other guys in the interim.  From that perspective, I could see how your being with one person for the span of a year seems like a more “serious” connection (in as much as a short-term relationship like that can be serious), while she didn’t find something comparable. She may feel threatened because you had a “stronger” connection with someone, or that there’s some inherent imbalance in what happened during your time apart. Hell, maybe she feels like this is somehow unfair, like you should have had to struggle to find someone but didn’t, while she was supposed to find the hot hot hook-up for her relationship rumspringa.

The only person who really knows what’s going on in her head is your girlfriend, so she’s the only one who can really explain what the issue is here. So you’re going to have to ask her what the deal is… assuming she knows or can put it into words. What ultimately matters isn’t what her grievance is and more how she’s handling it. Specifically, how this has become a weapon that she keeps using against you. This isn’t a rational issue. This is entirely about her and her feelings, her insecurities, and her sense of grievance over the relationship. It’s very much a her problem, but she’s trying to make it a you problem.

Much like taking back a partner who cheated, if she isn’t willing to forgive (in as much as there is anything to forgive) and move on, then she needs to say so and to walk away. It is fundamentally unfair of her to keep making this an issue with you when there seems to be no real way to resolve it. No amount of disclaiming the relationship with this other woman seems to satisfy her, no amount of reassurance is apparently enough to convince her that no, you don’t want to be with this other person. She seems to think more about your ex in the span since you’ve gotten back together than you did the entire time you were with her.

It especially doesn’t help that you’re basically stuck tip-toing through a minefield, never knowing when – not if, when – you’re going to stumble over yet another landmine that you have no reasonable or realistic way of knowing is even there. This sort of behavior is relationship poison; it’s impossible to have a secure and stable connection when some stray word, gesture or, I dunno, facial expression is going to set her off. This is a toxic dynamic under the best of circumstances, and it veers too far to an abusive tactic for my comfort, if I’m going to be honest. I don’t think she’s intending it to be a way of controlling you or keeping you off balance, but it sure as hell is having that effect.

Like I said: at the end of the day, this is a her problem, not a you problem, and she’s the one who’s making it the problem. If this is going to be a constant stone in her shoe, then she’s going to have to be the one to deal with it. Especially since apparently there’s nothing you can do, short of collecting the Infinity Stones and Thanos-snapping that timeline out of existence.

If talking to her therapist isn’t helping, then either she needs a different therapist or she needs to take a different approach. Maybe she’s not admitting to herself where this insecurity is coming from. I dunno. But you need to put down a boundary and say “Look, I’ve said all I’ve had to say on this. We’ve talked this to death and nothing’s changed and there doesn’t seem to be any way for me to reassure you, so I’m done talking about it. You need to find some way to deal with this because it never ends, it’s driving a wedge between us, and if you can’t find some way to move past it, we’re going to have to end this.”

And then you’re going to have to stick to that. You can’t lay down an ultimatum like that if you’re just bluffing; otherwise, all you’ve done is let her know that all your boundaries are just strongly worded suggestions.

Yeah, I know this sounds harsh. But sometimes folks need to get a bucket of cold water splashed in their face to make them realize what they’re about to do. If she’s not going to find some way of getting over something that didn’t involve her, wasn’t about her, happened after you two were no longer dating and has been over for nearly as long as it had gone on? Then there’s no point in continuing this relationship.

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 recently read your article on knowing what you want from relationships and I feel like I have a related problem that I could use your input on. Put simply, I (32 M) have a track record of leaving relationships at the wrong time. Most of the time, I end up staying in relationships for longer than I should, often when I probably should have left weeks or months ago. But at the same time, when I’m aware of this, I end up jumping ship when things are actually ok.  I probably should have stayed and made it work, but by the time I realize it, she’s already moved on to someone else and doesn’t want to give me a second chance. Sometimes I’m overlooking what are obvious red flags in retrospect and other times I think that things are ok but not great and THAT is a problem and I only realize that I was really happy after they’re gone. 

I realize that it’s me, I’m the problem, and I keep responding to whatever my last relationship was like instead of the one that I’m in. But I swear that every time I think I’m making the rational, informed choice. I’m not breaking up with people for weird little ticks or defects and I’m pretty sure I’m not staying in them because I’m afraid to be alone. Though my friends would say that maybe I am because I don’t stay single for very long unless I want to. 

I don’t know, Doc.  My friends are getting sick of me constantly asking them to take the temperature of my relationships and I’d like to feel a little more secure in my choices, but I’m not sure what I’m doing wrong. Do you have any tips for actually being sure whether I should listen to my gut, or if I should ignore it?

One Foot Out The Door

DEAR ONE FOOT OUT THE DOOR: OFOTD, I’m going to be real with you. Usually, I’ve got a good nose for fake letters, but this is one where I am legitimately unsure if you’re being serious with me or if you’re just feeding me ideas you came up with after binging Seinfeld episodes on Netflix.

I mean, God knows I know some people whose relationships have more drama than the Globe Theater but once the obvious answer is a George Costanza-esque “listen to whatever your instincts say and then do the opposite”, I end up wondering how someone like that manages to find people to date for longer than two weeks.

But OK, skepticism over, let’s actually address this, because fake or not, there’s actually something important here. One of the things I tell people all the time is to pay attention to their Spidey-sense; if your Spidey-sense is tingling and telling you that something’s wrong, that’s usually a sign. But trusting your gut or intuition or whatever you want to call it is predicated on whether your gut is actually trustworthy. And there are a lot of times when it actually isn’t.

People with avoidant or anxious attachment styles, for example, tend to run from relationships that are actually good and healthy because they have a hard time being vulnerable, trusting their partner or getting comfortable with emotional intimacy. People who are some form of neurodivergent and who have the rejection-sensitive dysphoria combo platter are often hyper-vigilant and on the look-out for signs that they’re about to get rejected; their Spidey-sense is keyed so absurdly high that almost anything trips it and they live in a regular panic that they’re about to be dumped.

And then there’re times when folks will stay in a relationship long past its expiration date – or when the parade of red flags has marched by again – because they’re afraid of being single or alone or starting over, or because they think that’s just how relationships are. And even if they do know, they may not have the guts to actually pull the trigger themselves to end it and are hoping that either things will get bad enough to force the issue, or the other person will do it for them.

I mean, God knows back in my bad old days, I stayed in a toxic and emotionally abusive relationship for years past when I should have left. Even when I realized that no, I needed to bounce, I still couldn’t bring myself to do anything about it, until life interceded and forced my hand on the matter.

(For the record, I strongly recommend against this approach.)

You don’t mention whether you’re in therapy or not, so I would suggest that maybe you should talk to a counselor, possibly with an eye towards understanding your attachment style. But it’s also possible that this is really a case of never actually interrogating the relationship that you’re in at the time and trying to figure out whether it’s working for them or not. Sometimes it’s a matter of being “go with the flow” to an absurd degree. Other times, it’s a case of being a “golden retriever” who’s all in immediately with minimal consideration and not willing to really look at whether this person is a good fit for you or not. But other times, it can be a case of not wanting to look too closely because you know there’s something not working, but you don’t want to actually know. After all, if you don’t know there’s something wrong, it’s not actually wrong… right?

So, in the name of working on calibrating your Spidey-sense and actually giving yourself a baseline to work from, I have some questions that you should ask yourself when you’re not sure whether it’s time to go, whether there’re some issues that maybe you and your sweetie could work on together, or whether the anxiety weasels in your brain are making s--t up out of nothing.

To start with: do you feel like you have a solid handle on what this relationship actually is? Are you sure that’s what your partner thinks it is? Do you think this is a relationship that’s leading to a long-term commitment or is it short term, whether by design or by necessity? I’ve seen people in relationships who have very different ideas about the nature of their relationship, where one thinks that they’ve been committed and monogamous since date three and the other thinks it’s completely casual because they’ve never had the DTR talk… or they’ve been dodging the DTR talk like Elon trying to avoid his various baby-mamas.

There’s also a lot of overlap with people who don’t want to ask or draw attention to the nature of their relationships because they know deep down that they aren’t going to like the answer. A lot of people in “situationships” are in them because they know if they try to put their foot down and say “what’s it going to be?”, that’s going to be the end of the relationship and they don’t want to face that. So they don’t… and then usually get dumped anyway when the other person’s done having fun and games.

The next question you want to ask is: how do you feel about the ratio of effort to reward? Does it feel like the level of effort you’re putting in is being matched by your partner? Is what you’re giving being balanced by what you get to a degree that you feel satisfied and that your partner feels satisfied? A seeming imbalance isn’t necessarily a bad thing; a relationship where you can’t believe what you’re getting compared to what you’re giving, where you feel unbelievably lucky to be with them and you’re punching above your weight-class can be a very good one. Especially if that feeling is mutual.

(By the same token, if they feel the same – that you’re incredibly lucky that they are with you – that’s a bad sign, and a good reason to get the f--k out so fast you pass into the Speed Force and retroactively erase the relationship from existence.)

How is your communication? Do you feel like you’re heard and understood by your partner? Do you feel like you understand your partner when they communicate with you? Or does it seem like the two of you are speaking different languages, talking past each other and spending more time trying to clarify what you said or saying “that’s not what I meant?”

How do you feel when you’re with them? Do you feel like you’re valued and respected, like your needs are being met? For that matter, how do you feel when you’re not with them or after you’ve left for a bit? Do you feel relieved when you know you’re not going to see them for a few days? This is different from appreciating some “me” time or needing your space. Knowing and enjoying your time apart is not the same thing as that feeling of relief, like a meeting you dreaded has been canceled.

At the same time, do you feel like you can be your true and authentic self with them, or do you feel like there’re aspects of yourself that you have to hide away or pretend that they don’t exist? I don’t mean flaws that you’re trying to work on or parts of yourself that you don’t like, but feeling like you have to pretend like you don’t have certain needs or wants or interests because your partner thinks they’re dumb, pointless or immature? Do they insist that you give up things that bring you joy, comfort or stability because they think you shouldn’t want them or have them or that grown-ass adults “don’t do that”?

Next question: every relationship has problems, but do you feel like the problems in your relationship are occasional and specific, or are they recurring and part of a pattern? Do old issues get resolved, or do they stick around while new ones get added to the pile?

Last and possibly most important question: are you still in this relationship because you want to be, because you’re afraid of being alone again, or because it’s easier to go with inertia than it is to actually risk change or having to start over?

You may notice that these aren’t binary or “yes/no” questions. Relationships can be complex and nuanced, like the people in them, and a strict “you want this many yes’ vs. this many nos’” isn’t always helpful. By digging into these questions – and the questions that those answers may bring up – you can start getting a better handle on whether this is a relationship that’s going well, one that might need a tune-up and maintenance check, or one where it’s time to bail. Preferably before it all goes haywire, messily and all over the place.

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 (39M) have been single and a virgin most of my life. Growing up I was always a shy kid (still am really). I never had trouble attracting girls, but they were never girls I was interested and seemed to struggle with the girls I WAS attracted to. I probably was a little too shallow for my own good (as I wasn’t entirely a popular kid) and did it in hopes of maybe finding a girl that would make me popular. As a kid it made sense or was worth a shot, but obviously looking back as an adult, it was rather foolish. So all that to say I had no dating experience at all in High school (no prom either).

In college I tried rushing into fraternities but never made it into one. My social skills weren’t always the best, and despised awkward parties, but I hung out with like-minded introverts. There were girls in our group, but they were either already spoken for, or ones I was not interested in. So I never really dated much in college at all either, except for maybe 1 time. I also did have a girl in a class that I hung out with a lot to study or grab food in between classes, that I thought was out of my league, but I just assumed she just wanted to be friends and thought she would laugh at me if I misread her kindness as interest. Turns out, she was interested, but by the time I realized it, it was too late. I really didn’t try too hard in college.

Post college is really when I started putting more effort into dating, but by then dating apps were starting to become a thing, so being an introvert that seemed perfect. I didn’t have to guess if someone was interested in me or not or feel embarrassed to find out the chatty girl I was talking too was just being friendly and is already spoken for. Anyways, so that was my dating experience for the next 12 years. Tinder, eharmony, Bumble, Match, Facebook dating, Hinge… you name it. 

I would maybe get an occasional match here and there and a handful of dates that never went past a second or third date. So, so far it has been rather dispiriting to say the least. I hold their interest very well over text and DM, but after a few dates it’s like the chemistry is all gone in their mind. It always threw me off because I would always leave a date thinking that person was promising, and I may finally have found a good match after a long 4 hour date, only for them to tell me later that I was “a super sweet guy, funny, and would make some girl lucky, but not feeling it”. They all seemed surprised I had never been in a relationship before when they always ask the dreaded “relationship experience” questions. 

I’m almost at a point of giving up on online dating. It seems like the women my age that ARE available to date online are there because they are a single mom going through a divorce, are a widow, or just not one bit attractive and in the same boat as me. So more likely to be open to dating a guy like me that doesn’t exactly look like a model. The older I get, the lonelier I get, and more easily “attached”.

I have been seeking therapy for social anxiety and depression, so I am actively working to improve myself and confidence, it just seems so hard to manufacture dating confidence when never given a chance, and my experiences seem to damage the self-esteem. I feel like I am a great person, and a lot to offer, but I guess I’m not selling myself very well

Long story short, my question really is, for someone who has been single all their life, struggled with anxiety, and reading social cues, and is ready to move on from online dating, what would you recommend for that person if they really don’t know how to navigate dating outside the online realm? I don’t know what I’ve been doing wrong. I’ve tried doing social groups of a common interest, but with no success. Help!

-Confused and Lonely

DEAR CONFUSED AND LONELY: ’m going to be blunt, C&L: your letter is one of the reasons why I keep banging the drum about how confidence isn’t built from success.

Your problem is pretty obvious, and I think you summed it up well, here – “I really didn’t try too hard in college.” But to be perfectly honest, I think you could leave off “in college”. It seems for most of your life, from high school on, you’ve been looking for the easiest option that required the least investment from you – from hoping to find a girlfriend that would make you popular, to putting very little effort into making friends or meeting people in college and afterwards.

Honestly, going by what you’ve written, you’ve spent most of your life doing your best to avoid having to interact with people or putting yourself out there and risking rejection. As a result, your social skills have atrophied and your social calibration is way, way off.

Now don’t get me wrong: I have a lot of sympathy and empathy for being a shy kid and not knowing what you were doing. Been there, done that, ended up spending amounts of money I don’t like thinking about to try to correct the problem in the most toxic ways possible. But there comes a point where you have to recognize that the avoidance and the shyness and the fact that you’ve always been trying to work around it instead of confronting it is the core of the problem.

Now, you talk about not having a lot of confidence and how your lack of success (and effort) hampered you in high school and college and how it’s continued from there. Well, that’s not a surprise because, as you said, you didn’t try very hard. The reason why I tell people that confidence isn’t born out of success is that confidence isn’t about knowing that you can succeed. Confidence is knowing that you can do the work that will help you succeed. Confidence is about survival and capability, not success. People, even confident people, fail all the time; sometimes through their own efforts, sometimes for reasons that have nothing to do with them. As the man famously said: it is possible to make no mistakes and still lose. But confidence isn’t about success or failure; it’s about getting back up after you failed and trying again. It’s about knowing that the challenge is going to be hard to overcome and knowing that you’re up to keep at it until you break through. It’s about knowing that failure isn’t going to kill you, that mistakes are there to be learned from, and that tenacity and effort will get you much, much further than innate talent. Confidence about being intimidated or nervous or even scared and doing it anyway, because you know that you may not succeed, but you’re going to give it your all, anyway. And if your all isn’t enough at that point, to know that you can dig down and improve so that it will be, the next time you’re in that position.

Success doesn’t bring confidence; confidence is what makes success possible.

So, in this case, it’s not that your lack of success hampered your confidence which hampered your social skills, it’s that your lack of confidence is part of what kept you from developing those social skills and increased your social anxiety. Avoidance doesn’t make anxiety go away; it just increases the things that make you anxious. Avoiding those just serves to make the world you’re able and willing to live in ever increasingly smaller, like the shrinking safe-zone in Fortnite or PUBG.

And because those skills get underutilized, you run into precisely the problems you have now – where you aren’t good at selling yourself, nor at reading signals nor at building and maintaining the connections with people that you need to build attraction and a relationship. You need those skills, regardless of where you’re meeting people – in person or on dating apps. There’s really no substitute.

To be fair, the dating apps as they exist now are increasingly awful by design. But even back in the day, when they worked as intended, the dating apps weren’t going to make up for poor social skills or an ability to connect with people. One of the mistakes people made back then – and still make – is to think that the app is anything other than a glorified introduction service. Nothing that any of the apps has ever offered or ever will – AI wingmen and Cyranos be damned – can replace the fact that you are still dealing with people and that means you need people skills. Yes, it means that you’re seeing people who are there because they’re single and looking for dates… but the same is true for speed-dating events and singles mixers. Messaging could be less anxiety-inducing than trying to talk to them in the flesh, but there was always going to be the point where you had to meet in person.

This is why success on dating apps has always been tied directly to your overall social skills and ability to connect with people. There simply is no skipping that step if you ever intend to actually, y’know, have a relationship with them.

(And then there’s the fact that there’s no way to tell whether you and someone else are gonna click the way you need to without actually meeting, no matter how good the messaging or even video calls were, so there would always be false positives. But that’s another issue entirely.)

You ask what someone who has struggled with anxiety and reading social cues should do if they’re ready to move on from online dating? Honestly, I’d suggest taking time to focus on the anxiety and social calibration. You’re coming to this late, but not too late (because there is no “too late”), so give yourself permission to build the confidence you want by doing the work. And its going to take work – a lot of work – to get where you want to be.

I don’t think you need to give up on trying to meet people entirely, but I do think your focus should be just on being more social, rather than trying to date. The skills you use to meet new people and make friends are the same skills you use to meet potential partners. But to do so, you’re going to have to be willing to deal with the friction that comes with meeting people. There’s going to be awkwardness. There’s going to be people who aren’t going to go out of their way to adopt their local introvert. You’re going to have to be more proactive, take the initiative more than you’ve shown thus far and be willing to make mistakes and maybe feel a little foolish. That’s part of how confidence is built – taking the hits and getting back up and trying again.

Put your focus there, and the rest will come in time.

Good luck.

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