Post Mortem: Career Opportunities

This week, we’re bringing back an older feature: the Post-Mortem. These are essentially longer Ask Dr. NerdLove’s, in which I break down just what somebody’s done right… and where it all went wrong. If you’re interested in a Post-Mortem, let me know in the email, and be sure to include as much detail as possible. Be aware: Sometimes the value of a post-mortem assesment is the application of the Sledgehammer of Truth, and the results aren’t always pleasant. So hey, fair warning.

Now with that in mind… here we go.

Hi Doc,

I’ve been following your site for a while now, and every so often I’ll start writing to you for advice which ends up helping me figure stuff out on my own. This one’s mainly a post-mortem to get your feedback on whether/where I messed up in this situation.

A bit of background: I’m a 24 year old student who works weekends as a supervisor at a Major Retailer. Had a couple online relationships with girls who I never even met when I was younger, but my in-person dating life has been less than a dozen dates. 

You’re going to have to pardon a slight digression, but this is a pet-peeve of mine that comes up a lot with nerds: online-only relationships aren’t relationships in the sense that you’re using the term.

There’s a profound difference between dating someone and having a “romantic” relationship with somebody that you’ve never actually met in person. No matter how romantic it is to think that you’re “getting to know somebody’s soul” or “getting to know the real them, without that physical aspect getting in the way”, or that this is somehow more “pure” than meeting in meatspace, the fact remains that sexual attraction is a key component of a romantic relationship and that can only be judged by being together in person. Even Skype calls and video chats don’t capture the physical aspects of the relationship; you’re missing the pheromonal connection, their presence and the hundreds of thousands of microissues – from the way they click their tongue when they think to the way they smell – that simply can’t be perceived outside of old-fashioned meatspace. I’ve lost track of how many hot-n-heavy online-only relationships collapsed as soon as they were together in person because they simply didn’t have the sexual, physical connection.

Not that I don’t believe that love can’t bloom in the online battlefield – I’ve got more friends than I can count who’ve found their significant other through forums and online games – but unless you actually make the leap to face-to-face, even if it’s long distance, it’s simply not the same.


Sorry. Please continue.

Earlier this summer, I ended up working an entire weekend with a newer coworker who I thought was cute. We ended up chatting a lot and having fun, and I noticed her showing a lot more interest in me than usual – one of the nights after the manager had said they need more people working for the following night, she said I should stay later to keep her company and that I should visit her on my break.

For those of you playing at home, this is what we in the dating-coach business call A VERY GOOD SIGN THAT SHE’S INTERESTED IN YOU.

During our conversations, she mostly kept the questions on me,

This is another thing to watch out for. If she’s asking you lots of questions, she’s very clearly demonstrating that she’s interested in you; she wants to get to know you better.

which felt weird, cause my usual conversation strategy is to keep the other person talking unless I have something to say.

I’m going to go out on a limb and guess that you don’t end up with long and involved conversations very often. This sort of tactic can feel very uncomfortable; it often comes off like an interview rather than an actual conversation. There’s a difference between being an active listener – going out of your way to actually demonstrate that you’re paying attention to what they’re saying by asking them questions – and just trying to let the other person handle the entire conversational load… which is what you’re doing. The point of a conversation is to actually communicate, which means it needs to be two-sided. Some conversations may start out weighted heavily to one person or another – especially if you don’t know each other – but they should balance out to around 50-50 in the end.

Something for you to think about in the future.

I was feeling pretty good about the weekend, and I gushed about it to one of my female friends (partly to get another perspective to help make sure I wasn’t building it up to be something it wasn’t). 

Ok, let’s go over things here:

She specifically requests you to hang around, come see her on your break and keeps asking you questions about yourself. Gee, I wonder what message she’s trying to send you…

I guess she could be a little less subtle...

I guess she could be a little less subtle…


I realize that a lot of guys feel like women are  Bene Gesserets whose every word and gesture is an exercise in sub-communication, but I’m not entirely sure how she could’ve been more obvious that she was into you short of pulling your pants down and crawling into your lap and wiggling.

(Of course, I say that as somebody who completely missed it when a girl more or less asked me to come up to her dorm room for a hot cup of “FUCK MY BRAINS OUT”, so I can relate.)

Later that week, around 3am, she texted me

NerdLove’s Rule #450: any text that comes after midnight and isn’t “OH GOD HELP ME I’M ON FIRE” can be safely read as “Hey, I wanna fuck.”

(I gave her my number when she wanted me to ask my roommate to trade shifts with her) and started telling me she wants to kiss my face and that she has a huge crush on me and that I have beautiful eyes.


My first assumption was that she had the wrong number, but she included my name, so her being drunk seemed more likely. She even said “Would you marry me?” and “I think I love you” toward the end of the conversation. I was texting her back, so it wasn’t like she was sending all of these out of nowhere, but still, it… kinda was out of nowhere.



Some drunk texting back and forth and saying things that are inappropriate is one thing, but this is a pretty big clue that your workbuddy has some boundary issues going on. Even if she was drunk on top of horny, alcohol is an enhancer, not a creator. It can’t make you interested in things you aren’t otherwise interested in, it just lowers your inhibitions and removes your internal filter.

So this is sudden trip way over the line is a strong sign that there’s trouble up ahead. In fact, I’m going to state now that there will be other, more dire red flags in your immediate future.

She sent me another text the next day to apologize. I told her I liked her too and wanted to get to know her better. Over the next week or so we kept flirting, and she started telling me more about herself, and red flags kept popping up.

Wait for it…

Some of them were easier to ignore than others. I don’t have any specific objections to dating a woman 17 years older than me with children who are almost my age, as long as she knows it’s not gonna be a serious thing.

… you know, this is probably something you might have wanted to mention earlier in the letter. Because this puts her behavior in rather different light. But still, not quite there yet…

 The one thing I couldn’t get past was that she told me she has a boyfriend.

THERE it is!

She didn’t want to talk about him much, but from what I could gather they’d been together for half a year and were sort of drifting apart.


I could only talk to her when he wasn’t around cause she said he gets nosy with her phone, which usually meant I couldn’t initiate anything without almost getting her in trouble.

Alternately: she doesn’t want to get caught cheating on her boyfriend.

Under normal circumstances, I’d be more inclined to think that her boyfriend was the nosy, quasi-abusive type she’s portraying him to be, but her other behavior seems to contradict it. Women who are worried about their boyfriends snooping on their phone and finding out they’re talking to other guys – especially much younger guys – don’t send bootie-call texts at 3 AM. 

One night after I had visited her at work, she texted me asking if I had wanted to kiss her.

Or, y’know, that.

I said yes, and when she asked why I didn’t, I pointed out that she was still with her boyfriend.



I will be the first to point out that my views of monogamy are nuanced at the very least, but this entire scenario is Bad Decision Boulevard.

She started talking about how she wants to be mine and she wants to spend the night together, which I took to mean she was ending things with her boyfriend.

Nope. It means she was looking to fuck a young hot piece on the side.

Subsequent conversations made me realize that she wasn’t,


and I finally broke things off via five-part text message.

Way to not think with your dick!


Lame, I know, but I could never keep my thoughts organized enough to explain my uncomfortableness in person.

Now, while normally I’m the person who says that break-up via text is a horrible thing to do, this was actually the right move. I will guarantee you that, should you have attempted this in person, you would have gotten the full-on production of tears, recrimination, loud declarations of self-loathing and the full court press of trying to get into your pants anyway and hoping that your dick was going to veto your brain’s decision. Being able to actually use your words – and in a way that you could actually make yourself understood, clearly and firmly – is the best thing you could do.

She took it okay, but when I heard she was quitting a month or so later, a narcissistic part of my brain insisted it was because of me. 


The problem is I sometimes find myself wondering if I should have gone for it, regardless of her relationship status.

Let me make this very simple for you.


My friends (including my best friend/roommate/coworker, who actually knew the woman in question) advised against “sticking it in the crazy” from the get-go.

That phrase makes me twitch, especially since I’ve used it before myself. Especially because your break-room bootie-call friend wasn’t acting crazy. A woman in her late 30’s wanting to bang some young hot piece of ass isn’t crazy, even if that piece of ass is almost literally young enough to be her son. What she was doing, however, is demonstrating some profoundly poor decision-making skills, a poor grasp of boundaries and – I’m willing to bet – a love of drama.

My new therapist saw no problem at all, saying I should live life and make mistakes.




Um… no.

I’m all in favor of making mistakes – not only is it part of how we learn, but often mistakes make for the best stories.


There’s a difference between making a mistake and diving dick first into the Thorn Bush of Very Bad Ideas. You said it yourself: there was red-flag after red flag waving at you, telling you that this woman was the very definition of bad news. No matter how hot she was, you knew on some level that this was going to be setting yourself up for the drama bomb that was going to go off in your lap. The problem wasn’t the age difference  or even the boyfriend. The problem was that this woman was looking for trouble and if she couldn’t find any, she was going to cause some and you were going to be at ground-zero. What you described is a very long list of bad decisions, half-truths and occasional outright lies – bad enough in someone your age who’s only responsible for herself… it’s potentially disastrous for someone who’s responsible for children. Even if she had broken up with her boyfriend, it would’ve been a mistake; you may have been interested in something “not serious”, but she would likely be considering it something entirely different… and then getting very upset when she realized that the two of you weren’t on the same page.

So really, the question you need to ask yourself is: “How badly did you want to be on your very own episode of the Maury Povich Show”?

I kept trying to justify it to myself, because I do want to experience a real-life relationship at some point, but I couldn’t shake that guilty feeling of being a cheater. Too many of my friends have been cheated on by their SOs. I don’t want to do that to someone else. 

Let’s be fair: this was at least 60% “Man, a blow-job would be nice right about now.”

Should I even care about that though? Am I stunting my personal development by taking on unneeded responsibilities? 


Second Guessing Self

Stop second-guessing. You did the right thing… and that speaks a lot to your character. A lot of other people would’ve dived head first in because, hey, hot chick wants sex! SCORE!

Y’see, even if the only problem had been her having a boyfriend, the last thing you want is to compromise your sense of morality just because want to get laid. That alone would weigh heavily on you and affect future relationships. But that wasn’t the only issue.

Under the best of circumstances, this would have been a tricky relationship to manage. As it was, this was a situation that, while potentially appealing, was well beyond your abilities to handle. This isn’t a slight on you; it’s simply that you simply haven’t had the life-experience necessary to handle negotiating something this complicated. This would have been the dating equivalent of going from playing Madden ’14 to suiting up for the Dallas Cowboys. No matter how horny or lonely you are, you really don’t want to come out of your first relationship with massive emotional (and possibly physical) scars.

If there’s anything you should take away from this, it’s that you’ve got good instincts and a strong sense of decency. You held back from a bad situation, even when parts of you had to be screaming to give in. That’s impressive, and not a lot of people could have done it.

There will be other, far better, opportunities for you in the future. Don’t beat yourself up because you passed up on a shitty one.

Good luck.

  • nonyabizz

    well played, doctor…

    • zenb!tch

      Well played SGS.

  • eselle28

    Yeah, this woman isn't crazy. She's an asshole. It's a good idea to avoid dating or sleeping with assholes too, because at some point their disregard for others ends up being pointed in your direction. Plus, this big ball of drama was bouncing around your workplace. Be glad she decided to go work somewhere else, because this could have blown up into something horrible.

    Don't worry about this being the missed opportunity that stunts your social development, either. Anything you might have learned in a secretive relationship with a person far outside your own age range who's an asshole and who probably chose you in part because you looked like easy prey is a lesson that's probably better not learned, and that might actually make it harder to be in a relationship with someone healthy. Why not pat yourself on the back for correctly reading the signs of both romantic interest and trouble ahead, and let the incident rest?

  • Vancouverois

    "What she was doing, however, is demonstrating some profoundly poor decision-making skills, a poor grasp of boundaries and – I’m willing to bet – a love of drama."

    So… crazy.

    Seriously: how does that not count as "the crazy"?

    • eselle28

      The idea of intersects too much with actual mental illness, and there's also a weird bit of gendering that comes with it. Switch the genders around and imagine if we'd gotten a letter from a young woman talking about how a male coworker in his late 30s with children and a girlfriend was pursuing her but lying about whether he was ending his relationship. We wouldn't call this person crazy. We'd call him a predator.

      • Vancouverois

        Who's "we"?

        I agree with nonA below. To me, the total lack of boundaries qualifies as "crazy" – it's a symptom of quite a few diagnosable mental illnesses. And while I agree there is generally a double-standard in how "crazy" is applied, I think the word would apply equally well if the genders were reversed. (And for that matter, I agree that "predator" also applies equally in this situation.)

    • Tea Fish

      Because none of those are symptoms of diagnosable mental issues, but poor character?

      Also because "crazy" used in a context like this is often gendered with a sexist bent. When you read about say, an older married businessman pursuing a much younger woman, how often do you hear people call that sort of behavior described as "crazy"? People might call him an asshole, or a cheater, or they might even laugh and say that it's to be expected, but they won't call him crazy because people like that are a dime a dozen. But a woman with a boyfriend pursuing a much younger man on the side? Crazy.

      • Ron Ritzman

        "Because none of those are symptoms of diagnosable mental issues, but poor character?"

        Actually they might be.

        However, Internet "armchair psychiatry" by strangers is easy. Only a professional after personally examining the subject can know for sure.

      • Vancouverois

        I agree, it isn't generally applied to men in the same situation.

        However, maybe it should be.

    • It's true that the meaning of words in English is rather flexible, but "crazy" to me means they:

      -key your car or destroy other property
      -show up at your door unannounced without any prior discussion of whether that's okay
      -make you feel unsafe
      -create dramatic situations (big fights) during inappropriate times
      -try to control you
      -kill your pet

      This lady, like the Doc says, has boundary issues and needs to get her head on straight, but no where does she seem to threaten, control, or make the LW feel unsafe or cut off from safety. Calling her crazy downplays the problems of people who have to experience ACTUAL "crazy" partners.

    • Cait

      Also, "crazy" seems to suggest an illogical, driven by uncontrollable impulses aspect. People who behave like this would LOVE to be considered crazy, because if they're crazy, well, they don't have to justify what they're doing or stop. Because hey, they're crazy.

      Instead, they're just people who are doing what all of us do: behave in ways that get us what we want/ need/ think we want or need with the minimal amount of effort. That's actually extremely logical. Why is she staying with both? Because they let her get away with it and she gets stuff out of it.

      By labeling her behavior as crazy, it removes all agency and therefore all responsibility from her.

    • nonA

      It’s not the age difference that makes her crazy. It’s the absolute lack of boundaries. You’re ignoring a rather huge chunk of the story to make the facts fit your point.

      If we’re going to play the “switch the genders” game, while it might take longer for the word “crazy” to be used if it were a man doing it, I guarantee you nobody would dispute the word when it did get used.

  • nonA

    24+17 is not “late 30s”. Even worse than it was before.

    Part of me says he should have gone for it, but only because we need to see things go thermonuclear up close and personal to realize just how messed up some people can be. You need a bit of cynicism if you want to navigate dating seriously.

    • eselle28

      Eesh, but even if you do want to see an explosion, I think it's a really good idea to set it off a ways away from your work. Especially when you're in a supervisory position. This woman strikes me as exactly the kind of person who's going to paint the relationship as him harassing her if he ends up not wanting something serious or if her boyfriend finds out.

      • Akai

        Seriously dude. You're advising something that could easily have lost this guy his job. Have some fucking perspective.

        • Kitsuner

          On the other hand, it WOULD have given me one hell of a story.

    • LeeEsq

      I agree with what Eselle says. I also don't think that you need a thermonuclear explosion to develop the appropriate level of cynicism. Some rejections or ordinarily bad encounters rather than extraordinarily bad encounters work fine.

  • Phoenix

    Second Guessing, you did the right thing.

    This woman is just a selfish jerk that would have probably pulled you and her boyfriend along by the string, and caused a whole bunch of trouble for yourself. She probably saw you as an easy piece of piece of meat for her to dive in when her boyfriend is cold feet or whenever she's bored.

    And let's also not forget that you two were coworkers. You could have used that to her advantage as well to keep you stuck with her or just to make your life miserable. You could have been forced into a situation where every coworker hates your guts or WORSE, you would have been out of a job. And for what? Just for a fuck? Definitely not.

    I think your therapist doesn't sound so good at this either. There's a difference between making a mistake and possibly fucking up your life. The fact your therapist suggested you went for it doesn't sound good.

    You saw that she was no good and you stuck to it. Good on you.

    • Phoenix

      Sorry, my grammar is bad.

      When I was talking about the working part. I was saying that SHE can use the fact you two are coworkers as her advantage to either keep you with her or just to make your life worse. ESPECIALLY since you are her supervisor.

      10 bucks says that she would have blackmail you into the following:
      A. Marrying her
      B. Stealing from retail
      C. Fucking her brains out whenever she wants

  • Jess

    I agree, you didn't miss out on anything, you had great instincts and saved yourself a load of drama and trouble that just isn't worth it.

    Good work!

  • Kitsuner

    LW here. Reading this was definitely a nice bit of validation, especially for the parts where DNL acknowledged that going against his usual advice was the right move for the situation. I was a little worried with his intro about the Sledgehammer of Truth, but good stuff all around.

    "Let’s be fair: this was at least 60% “Man, a blow-job would be nice right about now.”" had me rolling.

    • Hopefully, you did find a new/better therapist?

      • Kitsuner

        Well, that was one of the first things we talked about, so I figured I ought to give it some time before deciding it wasn't a good fit. Three months later, I'm still meeting with him, though I've definitely considered switching or just stopping therapy altogether for a while. I think we're starting to reach the end of the early uncomfortable stages, but it's taken longer than with other therapists, so I dunno whether that's on him being a "bad" therapist, me taking too long to get used to the shift from my previous therapist, or some combination of other things. At this point it's just easier to keep working at this relationship than starting from scratch.

  • LeeEsq

    When a date is asking you questions, how do you tell the difference between obvious interest and politeness? I've had dates that asked me a lot of questions, at least seemed interested in my responses, and then never got back to me or rejected me afterwards.

    • eselle28

      Well, there are the usual body language and tone things that indicate that someone likes you, but beyond that there's not some perfect way of knowing. Asking questions and seeming interested in the responses is pretty much a requirement for being a good date, and a lot of people feel obligated to do that even if they're not interested. It also might be that the woman was interested and that one of your responses gave her the information she needed to decide the two of you aren't compatible (I've certainly had that happen a few times).

      Specific examples might be more helpful.

  • Phoenix

    Can we give Second Guessing Self a new nickname?

    Seriously, we should just call him "Dodging the Bullets Matrix-Style)" or DtBMS for short. Or maybe just "Dodging the Bullets".

    Cause, really, this guy is awesome and the fact he is second guessing himself makes my head scratch.

    • Kitsuner

      Hahaha, thanks. I can dig some DtB action. But yeah, as annoying (and occasionally paralyzing) as the second-guessing gets, it's a really difficult habit to turn off. It'll probably go away as I get more life experience, but that's just another way of saying I have to stop second-guessing myself before I can stop second-guessing myself.

      It's definitely frustrating though.

  • Dallian

    Yes! Thank you for the Dune Reference!!! 😀