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.