Ask Dr. Nerdlove: I Can't Get Over An Affair With My Married Boss

Hello, Internet! Welcome to Ask Dr. NerdLove, the only dating advice column with a gamerscore that's over 9000.

This week, we're going to be doing things a little differently. Instead of answering two or three separate questions, we're going to go more in depth. Occasionally, I'll get a question thats more complex than usual and requires a little more exploration to pinpoint exactly what went wrong and how to fix things.

Keeping with the doctor theme (Doctor NerdLove is not a real doctor), I call these Post-Mortems - cutting into the cadaver of the date or relationship, weighing the organs and trying to determine a cause of failure… and, critically, what to do afterwards. It's not always pretty, but it's frequently necessary.

This week, we've got a twisted story of love and loss and emotional abuse between a young man and his on-again, off-again girlfriend. Snap on some gloves, it's time to start cutting.

Hello my name is Jack and this is my love question, nay, my love story.

I have dated here and there and haven't had a true girlfriend since my last true love. She used to be a coworker of mine....my boss actually, at a record store.

I see no way this could possibly go badly.

When we were officially introduced we had a nice little chemistry. There would be times when I caught her staring at me or when she would hurry up to walk out the door when I held it, it was a sweet Amelie style of affection. I was always taught to wait until the moment embraces and truth be told I had no idea that she had a crush on me for months until a friend of mine got the inside scoop (which I gained confidence to go in for the kill). You may ask what took so long to date her, well, she was married to somebody who was in the country illegally and also had a 3 year old son. And yes, I dove in to the "other guy" territory, leaving a black mark on me that has carried for years.

Honestly, I think you were always going to have bigger problems with this relationship than just being her manstress. To start with: she was your boss. It's pretty much always a bad idea to get involved with your superior at work - ignoring the fact that there can always be the issue of power differentials, there's also the fact that it can make things difficult for everyone else at work. The most obvious issue is perceived (or actual) favoritism, but there's also the fact that, if things go wrong, she can fire your ass. This puts a WHOLE lot of complicated issues in play, not the least of which being that she could conceivably hold your continued employment over your head to make you give in and play ball.

When we were first "dating" we were love lured, acting like kids, never worrying about the world. Looking back that's where my denial kind of began. It was the prime of my life at 23, heading back to school to complete a degree...but she was an anchor of mine and I slowly became impatient with her situation with her illegal husband (divorce sometimes takes up to four years for an illegal/green card process, and lots of money).

Aaand I'm going to stop you right here, and we can begin to really post-mortem this. Here, you fell victim to one of the classic blunders, the most famous of which is "never pretend you're her friend to get in her pants" but only slightly less well known is this: No matter what they tell you, they are never going to leave their spouse.

This is a universal truth, regardless of gender. If they were going to get divorced, they would've done so already or it would already be in process. Instead, they're having their beefcake and eating it too.

There will always be reasons: They have a child. She can't afford a divorce lawyer. Their finances are too intertwined and leaving now would leave him financially ruined. She wants to make things work. Or, in this case: Leaving means her ex-husband would get deported.

Pending further evidence I'm going to be charitable and assume that she wasn't leaving her husband because she's not evil and didn't want him thrown out of the country. That alone is a pretty powerful motivation not to leave until his legal status has been resolved and - as you've said - that can take years.

However, even if that weren't the case, she really had no motivation to actually go through the process of leaving him. Even when there aren't extra legal issues in the mix, a divorce is a long, messy and expensive prospect that takes its toll on people even when they're dying to get out of the marriage. But thus far, aside from the fact that she's bangin' somebody at work, she hadn't been showing signs that she actually wanted out of the marriage. As it stood, she had her marriage and her piece on the side (you)… why screw up a good thing?

In fact, without reading further, I'm going to lay my money down: You're about to get caught up in a whole lot of "come here, go away". As soon as you make noises about ending things, she's going to dangle the potential of her leaving him like tasty, sexy bait in front of an especially horny shark.

I always wanted her to be honest with her husband either way, just letting him know the scoop. I of course was too cowardly to tell him because she early on told me he is unpredictable and highly emotional, likely to make a stupid mistake.

Of course he is. They always are. There's no better way of keeping the piece on the side from getting in her husband's face than by saying, "Oh, and he's kinda crazy, so you better not talk to him." It's also a great way to keep the White Knights on the hook; now not only are you banging out, but you're also helping save her from her possibly-abusive-in-the-future husband!

I never said anything.

Because of course you didn't. You're already in a tricky situation: you're the other man. You've already been given hints that he's "unpredictable" (read: potentially violent). This gets reinforced by the fact that, ethically speaking, you're in a weaker position by default. He's the wronged party, and that's going to put other people on his side. Between the vague threats of violence and your sense of guilt, you've basically been manipulated into not rocking the boat.

Before I went to school she told me she loved me but she also considered breaking up with me for her baby. To be honest I did not know why the hell I still somehow stood by her.

I'm going to go ahead and guess the answer was "sex."

It could have been an unofficial breakup but we still fooled around.

Yep! Sex.

She was a very happy person whenever I was with her and we did have that optimism, but I slowly grew jealous and wanted her to do more of the emotional work. I took a break from her, and she was out of it. We still had nights, and moments but one night she came back to me the sweetest way possible. We were watching tv, I was laying on my couch while she was sitting on another. She slowly inched towards the tv, like a child trying to find the dots of the tv. I couldn't help but to fall in love with her (and that still is the sweetest thing to happen to me).

We tried dating again. I flunked out out of school and was still working with her. Some days it got too tense and emotional for me. I felt like I was bipolar. I would be high on the love but also addicted to the sadness of the situation.

Not to put too fine a point on it, but you were getting forbidden nookie and oodles of drama. That was what was keeping you around. You already knew this was a bad situation, but the combination of sex and feeling like you were secretly the hero of this story is combining to make you feel like a character in a movie. At this point, there almost had to be some part of you that knew there was no way this was ever going to end well.

We had communication problems. To be honest I always felt like she should know the answer that I wanted for us. I wanted her out of her husband's life and to be in mine, but I never said it. I never really said 'I love you' in that way, because I always felt she had to make that jump. I could have said it but I am not sure, and sometimes I feel like she knew all along but just didn't want to do it.

No shit.

OK, I know this going to be harsh but, she knew how you felt; no matter how many times you two broke up, you'd be right there to take her back. And in the spirit of total honesty, you were hoping that she was going to make the move because you had no leverage here. As the person with the most to lose - and as the one who was, frankly, manipulating you - she was the one who was in charge of the relationship. There's a part of you that understood this. By telling her you loved her under these circumstances, you would be almost pleading for her to leave him. No matter how much you may have loved her, that would've been humiliating. In the long run, it was better that you didn't say it. Better to swallow it and let it remain unspoken instead of possibly losing more self-respect to an already crappy situation.

But in her defense, she has a whole life with her son there in the picture and his dad. Her son was a gifted child, already knowing two languages and his surroundings, very excitable. I always watched him like a hawk to make sure he never fell down; and we were pretty good playmates. My last meeting though was a unfortunate one. We were at Red Robin and her son had a coloring book. He was going super fast with it, not really coloring it. I was trying to help him but I was being really forceful and ended up grabbing his crayon and he was crying.

I immediately was flustered and told him he wouldn't get a balloon. I made that promise but when I did my girlfriend had the most let down face I have ever seen; I swallowed my pride and got him the balloon and immediately felt like a stubborn six year old.

So here we have another another example of why this whole thing was a bad idea.

Dating a single parent is not something to be entered into lightly. Dating someone with children means you're not just in a relationship with that person. There's a child or children involved as well, and if it's going to be at all serious, then you're going to be a part of that child's life. That is an incredible responsibility and one that needs to be taken very seriously.

You were 23, just out of college and working in a record store. You had no life experience, very little relationship experience and - critically - were probably not in a position, emotionally or financially, to be helping raise someone else's child. And make no mistake: even with his biological father in his life, continuing the relationship with this woman would mean that you would be a parent to him. And just going by your response in this situation, I'm guessing that you probably weren't ready for that.

Moreover, considering that this relationship was pretty much doomed from the jump, staying involved was actually pretty unfair to her son. By bonding with him, you became a part of his life. When (not if, but when) you broke up with his mother, you'd be taking that part of his life away. To a child that can be devastating, especially considering the tensions at home between your on-again, off-again girlfriend and her husband.

I held him up and whispered in his ear "always take care of your mother." That is the truest statement I have ever said to anyone and I just hope he does the same. It was a slippery slope, almost a year after being back together, we had a fight and she told me she can't be with me anymore.

I'm giving it two more paragraphs max before she's trying to get back together.

I tried going back but my friend's girlfriend set me up on a blind date. I was still Facebook friends with my ex and one thing lead to another she got super jealous.

Nailed it.

Payback? You bet. I had an alright relationship with my new girlfriend, but in the back of my mind I had my love reserved with my ex.

Dude. Dude. I don't know if you realize how unbelievably shitty this is to everyone involved. Parading a new relationship in front of your ex just to get back at her is a huge dick move on your part.

But it wasn't just your ex you were hurting. You dragged an innocent bystander into your relationship drama. Treating another girl as a placeholder for the one you want is an even bigger dick move, because she is going in under the assumption that you're acting in good faith. You were basically using her and toying with her emotions because you need a warm body to fill the spot marked "girlfriend" until your ex came around and finally dumped her husband. Which was never going to happen.

The kindest thing you could've done here would be to cut ties with both women. Take the nuclear option with your ex and cut all contact, then break up with your current girlfriend because what you were doing wasn't fair to her, either.

This was my warning to her, but of course, very reckless. She still didn't give up the husband and we met months later and had a mini hook-up, but it wasn't the same. At this point she wouldn't even confess that she was still working things out with her husband.

By this point, you really needed to realize that unless she specifically had said "I divorced him," nothing had changed. Because nothing was going to change, and nothing will change in the future.

One day, I asked about what is going on, and she mentioned "If I told you everything, you would leave me." And she never said anything else about it. Now my denial intensified. I still blame myself for the relationship we had. Much later I wanted to help and she yelled "how can you help me?" She was right, I was broke, had no good career and haven't even moved out of my father's place. I was hopeless.

See, this is one more reason why she wasn't going to divorce her husband for you. Ignoring the fact that she clearly wasn't interested in divorcing him period, you were in no state to be trying to maintain a family. She knew exactly what your career prospects were because she was your employer. No matter how much she might have been enjoying the sex and the new relationship energy, you were in no position to be maintaining a long-term, stable relationship, especially to a single mother.

Here's the thing though: You weren't hopeless, you were young. You were barely out of college - at this stage in your life, your goal is to start building a life where you could get to a point where you were ready to support a wife and children if that's what you wanted. This situation would be a lot for anyone to deal with, and kicking yourself for not being able to instantly handle things is being unfair to yourself.

One day she ended things. Never mentioning how she two-timed me…

Wait. Unless there's something you haven't included in here, she wasn't two-timing you, she was two-timing her husband.

...nor how she lied herself, even though I have confessed my lies. And this breakup still haunts me two years later. There was a day where she said she would love nobody else but me. And looking back now how I wished to say that I would do the same. It just doesn't make sense anymore, can somebody really love me like that?

Holy crap dude. I realize you're still hurting, but I think you need to understand how manipulative it was for her to say this. You need to realize: you were being used. She knew how you felt. She knew she was never going to leave her husband for you. Dropping that little bomb on you was just a way of keeping you on the hook in case she decided she wanted to pick things up again. That's not love, not in my book.

Yes, after we broke up there were drunk texts and one time I actually went to the place where her husband worked; we have met before and I believe he remembered me. I had a photo in my wallet of us kissing and I wanted to embarrass him, to put her down a notch, but I deeply could not predict if it were to be an event leading to someone getting hurt.

Yes. Someone would get hurt. First, assuming he didn't know, he'd get hurt. And then, because you just walked up and showed him a picture of yourself kissing his wife, there's a pretty good chance you'd get hurt, too.


For all I know she has never told him and never will, or in the extreme case has told him the truth but in small detail and limited knowledge. I held back and am ashamed for being stuck in this downward spiral. I only drink alcohol and now alcohol either helps me or it doesn't, a small seed of guilt every time I drink because I don't feel like I am progressing my life.

Now with that out of it, I just need to ask your advice on how to be a better person after this ordeal. Not necessarily to move on because that's obvious, I know I do have to move on. I do admit, I along with many guys tried to become the "real guy" instead of the "other guy." But how can I move on from being in such denial, and this thought process that she would come back? I thank you for reading this long email and just your insight. I have asked many people but not the right answer that I am looking for. No pressure on you of course, but it would help.

— I Am Jack's Shattered Love Life


Let me start by being blunt: Getting out of this relationship is the best outcome you could have hoped for. None of it was healthy - not your obsession with her, her continual cheating on her husband with you, letting her son be involved in this, none of it. This was one very long shitstorm of epic proportions and you should be grateful that you've gotten out of this with as little psychic and emotional damage as you did.

I've no doubt that your ex cared for you (kind of) - most people aren't going to keep up an affair that long when it's just sexual attraction - but the fact of the matter is that you were being used. Her marriage was the main event; you were a side attraction. Maybe she needed something to make her feel desired. Maybe she was legitimately having problems with the marriage and needed an outlet. Hell, maybe she had an arrangement with her husband. But at the end of the day, you were the secondary party in this. She was never going to leave her husband. She never gave you any indication that she actually would. And the fact that she kept this going this long and kept coming back meant that she knew that she could always rely on you to come when she called.

But it's all fallen apart, just like it was always going to, and now you're left in the rubble wondering what to do about it. And the answer is simple, though difficult to do. You said it yourself: You have to let go and move the hell on.

I know this sounds harsh. You're in a lot of pain and your life has gone to shit because of all this. I sympathize. But what you're doing right now isn't healing, it's wallowing. You're drowning yourself in misery because part of you is still treating this like an epic love story instead of the profoundly dysfunctional and toxic relationship that you should be glad is over.

So here's what you need to do to get past all of this. First of all: it's time to lop off this part of your life. It's over and done with. You need to cut it off and cauterize the wound, because you're letting it fester and that infection is going to continue to ruin your life if you let it.

That means it's time to unload everything from that relationship - all the mementos and keepsakes, everything - and get them out of your life. If you're still at the record store then for God's sake, quit already. You need to remove all traces of her presence and that means going the full nuclear option: block her on all the social media you have, delete her phone number, trash her emails and get rid of every single way you have of contacting her. You're starting a new chapter in your life, and that means you need to have a completely blank slate. Having reminders of her is only going to be an opportunity for this cycle to restart.

Next: you should strongly consider talking to a therapist. This was an incredibly unhealthy relationship and you're dealing with real emotional damage. You need to be able to unpack this with somebody who can help you start to put the pieces of your soul back together, and that means talking to a professional.

Fortunately, you have resources. If your college's health department doesn't have a therapist or counselor on staff, they should be able to help put you in contact with someone who can help you.

Ah, but you flunked out. Well, that brings me to the next thing you should do: Re-enroll. Start going back, even if it's just on a part time basis. Because while you're working with a therapist, you also need to start picking up the pieces of your life and putting them back together, and that means getting your education back on track.

In a lot of ways, you're not in such bad shape. You're young, you have few responsibilities and - hopefully - relatively few debts. You're in a position where you can start over. It won't be easy by any stretch. You're going to have to work incredibly hard just to get back to the starting point again… but you can do it.

For now, doing that should be your only priority. Not dating, not being the "real guy," not dealing with rebound relationships; just focus on finding a new job and getting your finances and your education back on track. That's enough.

If and only if you a) have a steady job that isn't at the record store and b) have completed at least one new course credit towards your degree should you even consider going on a date with somebody new.

And while it should go without saying, one more rule to set for yourself: No more married women. Ever.

It's going to be a long, trying road ahead of you, and it's going to suck like few things have sucked before. But if you put your head down and plow through it, if you give it your complete and total focus… you'll get through it. And in the end, you'll be a better and wiser person for all the pain that you've gone through.

Good luck.


Do you have a story of a date gone wrong and you don't know why? Not sure why things didn't work out with your crush and want someone to show you just where and how things went wrong? I'll continue to take some longer letters to perform another Post-Mortem like this one sometime soon. If you have such a story, send it in and let me know you want it considered for a Post-Mortem.

In the meantime, share your thoughts and stories in the comments section, and we'll see you in two weeks with more of your questions!


Ask Dr. Nerdlove is Kotaku's bi-weekly dating column, hosted by the one and only Harris O'Malley, AKA Dr. Nerdlove. Got a question you'd like answered? Write doc@doctornerdlove.com and put "Kotaku" in the subject line.

Harris O'Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new book Simplified Dating is available exclusively through Amazon. He is also a regular guest at One Of Us. He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.