Hello, Internet! Welcome to Ask Dr. NerdLove, the first dating advice column to survive the Battles of Yavin, Hoth and Endor.

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This week, we’re talking about doing the right thing, even when every cell in your body is telling you to do something else. Whether it’s recognizing a deal-breaker when it’s presented to you or recognizing that what you want would be the worst thing that could happen, sometimes you need to recognize that you’re about to walk right into that buzzsaw.

Let’s do this thing.

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Dear Dr. NerdLove,

I’m a guy in my early twenties who has had a pretty much non-existent love life after having broken up with my first long-time girlfriend about 3 years ago. I’m overweight with some pretty serious confidence issues, so it took me way longer than I would have liked to get back up on the horse. However, a few months ago I decided that it was finally time to get back into the dating game and look for a girl. A few weeks after that decision I started a new job and met the most amazing girl. We hit it off instantly and I knew right away that I was into her. She’s cute, funny, and she laughs at my jokes. Jackpot. We started chatting more at work and soon enough we were texting and talking outside of work hours. Then she tells me that she has a crush on me and I tell her I feel the same. We quickly became infatuated with each other, have hung out a few times, and it’s looking like there’s a really promising relationship on the horizon. I haven’t felt this happy in years and I love that she makes me feel this happy.

But here’s why I’m writing to you. Ever since she told me she was into me, she’s been warning me that I shouldn’t fall for her and that she always ends up breaking people’s hearts. We were chatting

tonight and I pressed the subject and she finally told me that she has pretty much cheated on every guy she’s ever been in a relationship with (she’s two years older than me so she’s the more experienced in terms of relationships). Now I’ve never cheated on a partner or been cheated on, but I’ve always found even the thought of it to be reprehensible, so much so that just thinking about being cheated on puts a knot deep in the pit of my stomach.

She says that she cheated because she has a short attention span or because she gets hurt and wants to hurt back. I don’t want to sound like a hopeless romantic, but she tells me that our budding relationship is like nothing she’s ever experienced; I make her laugh more than anyone has and I’m not like any of her previous love interests. But what I found bizarre was that she cheated on her old boyfriends as a child of divorce after her mother cheated on her father. I can’t understand how someone who was hurt so bad by infidelity as a child can practice it herself.

I guess what I wanted to ask you Doc is what should I do? Is this a deal breaker? Am I an idiot to assume that our relationship won’t end the same way her previous 4 or 5 have? Can I make her change? If we give it a run and it doesn’t work out, that’s fine by me. But just the thought of it ending by being cheated on makes me feel ill. I’ve never felt so suddenly into someone as I have with this girl, but I’m questioning whether I should even bother giving it a chance. Please help me out.

Sincerely,

Sick to my Stomach

Before I get into the weeds, StmS, let me start off with this important piece of advice - one that will serve you well in your dating adventures and something that I wish people had told me back in the day: you can’t make anyone change. If your future happiness is dependent on making a radical change in the other person’s personality, then that relationship will not work and you will only be contributing to your own broken heart.

Now with that out of the way, let’s get to it. Because there’s a lot to chew over in your letter.

First: when someone tells you that they’re trouble - not in that “James Dean” way or the “Bad-Girl-With-A-Heart-of-Gold-Who-Mostly-Just-Smokes-Weed-On-Occasion-And-Listens-To-Emilie-Autumn-And-The-Birthday-Massacre” kind of way - believe them. Your crush has laid out, in point-by-point fashion, just what’s likely to happen when the two of you date. She’s not asking for someone to save her from herself, she’s trying to let you know that in all likelihood, she will cheat on you if you ask for a monogamous commitment from her.

Why? Well, that’s a good question, but ultimately an irrelevant one. Maybe she has a self-destructive streak and pushes away people because she doesn’t believe she can be loved. Maybe she’s modeling her parents’ relationships. Or maybe she’s just one of those people who’s not monogamous, but still keeps trying to force herself into the traditional relationship mold because social conditioning is a motherfucker.

But for your purposes it doesn’t matter because you are not her therapist. You are not here to “fix” her (whether or not she needs fixing in the first place), nor do you have the tools to do so even if you were. Trying to do so is only going to hurt you both. She’s going to feel like you’re judging her (and to be fair, if you try to change her, you kinda are) and she’s going to be hurt and, by her own words, act out in return.

You’re exhibiting the same logic that leads to people dropping hundreds of dollars on Powerball tickets with the same result: someone may win eventually but it’s almost certainly not gonna be them. You are going to end up getting hurt because she has a pattern to her relationships and you’re banking on being an exception.

You almost certainly aren’t going to be that exception.

Now here’s the thing: the fact that she’s told you all of this means that she really does like you. She’s self-aware enough to recognize this behavior in her and to know she’s not in a place to change it yet. She doesn’t want you to get hurt and the odds are that this is exactly how it’s going to end if you two date.

Should you date her? Well, that’s up to you. Personally, I wouldn’t, were I you. Even if you go in knowing what she’s like and what’s likely to happen, it’s going to take some serious emotional fortitude and a willingness to take a lot of emotional gut-punches in the process. Even if she makes the effort to change while you’re together, you’re still going to go through a lot of pain and conflict.

You have to decide whether or not what you have and the way you feel over the course of things is worth the price, which may wind up involving her cheating or otherwise self-destructing the relationship. Is a relationship worth it for you if 90% of it is happy but the last 10% isn’t?

Now there is one possible way to thread this needle. I wouldn’t necessarily recommend it for you because it won’t work for a lot of people: you date her without an expectation of sexual monogamy. One person can’t cheat if the two of you aren’t exclusive. If and only if you can handle the fact that she’s not monogamous with you, then you might be able to give it a try. Books like Opening Up by Tristan Taormino and More Than Two by Franklin Veaux and Eve Rickert can provide some guidelines if you want to go that route. But if the thought of her being with someone else causes you physical pain… then yeah, that’s going to be a deal-breaker.

Regardless of what you decide, remember: you can’t make someone change.

Good luck.

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Hi Doc,

Let me preface this by saying I am not an attractive man. And I mean that in all senses. I’m fat, ugly, self-loathing, milquetoast, and have absolutely no confidence. I’m in my mid 30s and have long ago (mostly) made peace with the fact that I will never have a fulfilling love or sex life.

So anyway I met L a few years ago and we became close friends. Smart, funny, sweet, kind and beautiful. She also had a fiancé, J, who’s a pretty great guy. At first I crushed on her hard, but I’ve gone through the whole fall for an unattainable woman thing before, with predictable and unfortunate results, so I quickly let those feelings go and made sure to only think of her as a friend. She didn’t make it easy because she’s a very touchy-feely person and I’m not accustomed to the casual touch of attractive women, but I persevered. When she and J got married, I had a blast at their wedding, made a fool of myself on the dance floor, and was genuinely happy for them.

L had mentioned several times that she thought I was good looking, often loudly to friends and complete strangers alike. She even told me once that if she had met me before J, things may have gone differently. I always just thought she was just saying stuff like that to try to boost of my self-esteem.

Cut to the other night. I went to a buddy’s house for game night. L and J were there too. At the gaming table I sat next to L with J on the other side of her. Beer was flowing generously, though I was the only one not drinking. At one point my buddy’s cat jumped on to my lap. I petted him for a bit and so did L. Eventually her hand slid off the cat and onto my thigh. At first I thought the alcohol had made her extra touchy-feely, but then after the cat jumped off, her hand slowly moved up my leg. I froze. I didn’t know what to do. She slipped her hand underneath my shirt and started raking her nails across my back and side. And it felt good. Really good. I had no idea I was into that kinda thing. Look at me learning about myself. Anyway, her turn comes around and she retrieves her hand much to my relief and disappointment.

A little while later we all decide to take a to pause the game for snacks and restrooms. It’s customary for L and I to take a smoke break during these pauses. We stepped out, but instead of standing on the back porch in front of the sliding glass door like usual, she walked to the side of the house away from doors and windows and prying eyes. I followed but kept my distance, and asked her what was going on. She was evasive and wouldn’t directly answer any of my questions. Instead she asked me if I’ve ever had a woman take control, and then pressed her body to me. My previous train of thought derailed, and I instinctively put my arms around her and held her tight. We were millimeters from kissing, but then I had a sudden thought of J inside the house not 50 feet away. It was difficult as hell, but I pulled away. She was grinning.

We went back inside, and the rest of the night passed quickly. She would sneak in a touches and gropes whenever she could. I could have stopped her, but I didn’t, and I liked it. At the end of the night, as the three of us were walking out together, a very drunk J realized he forgot his jacket and ran back inside. The moment he turned his back, she quickly drew me in and licked my cheek. Turns out I don’t find that hot. More learning there. But the intention was clear. Then we parted ways.

So, yeah, I have no idea what to do now. I mean I know I should try to get some answers from her, but I’m not sure how to go about it. Her friendship very is important to me, and I don’t want to damage it. And I definitely don’t want anyone else to get hurt. Maybe it was a one time thing. Perhaps she was just teasing me, and so long as I don’t bring it up, it won’t be an issue. Or maybe they’re opening up their relationship and she wanted to test the waters. Probably wishful thinking on my part.

But what if she simply wants to have an extramarital affair behind her husband’s back? I’ve made so many mistakes through inaction in my life, maybe just this once I should do something wrong on purpose, eyes open. I will never have the chance to be with a woman this gorgeous again. I could live in the moment as hard as I can, then bear with inevitable disastrous fallout.

And that, of course, is a terrible idea. So I guess my question is, if I find myself in a situation with her that is heading for a place I know is wrong, but every cell in my body demands I go with it, how do I generate the willpower to say no? Greater men than I fail at this all the time.

Thank you,

Discombobulated

Hoo boy, Discombobulated, I’m glad you’ve written to me before you’ve done anything, because right now you’re on the path to sticking your dick in a buzzsaw. Not that I don’t doubt that the sex would be great and she’s an amazing person, but the likely fallout would be far worse than you realize.

Now in general, I don’t believe that sex necessarily ruins a friendship, but in this case, we’re talking about consequences that go beyond just the two of you.

Let’s game this out a little so you understand where I’m coming from here. You hook up with her. In all likelihood, she does not have an arrangement with her husband for a little off-leash time which means that she’s just cheated on her husband with you. If and when this comes to light, then you will have seriously hurt J, someone who trusts you and who has been a friend to you. That’s a pretty shitty thing to do to somebody you think is a great guy.

Then there’s the fact that you have overlapping social circles. This is the sort of gossip that shoots through like wildfire and people will have very strong opinions about who was in the right and who was in the wrong. You will more than likely find a whole bunch of your friends do not appreciate you being instrumental in damage to L and J’s relationship.

Now let’s say that through all of this, L and J manage to pull through L’s infidelity and make things work. One of the things that would almost certainly be part of their reconciliation is ensuring that she wouldn’t make the same mistake again. That means never seeing you again… which in turn would likely mean you being exiled from the social circles where they are fairly prominent.

That’s more than just ruining a friendship, that’s ruining many friendships, potentially a marriage and needlessly hurting more than a few people in the process.

And let’s say that, unbeknownst to you she’s having problems with J.Then you’re less a sex partner and more the hammer she’s dropping on his nuts. Trust me: the sex ain’t worth it if you can’t live with yourself afterwards.

Now, odds are that she was drunk and feeling a bit horny and she decided that maybe a little naughty fun was in order. Even so: that’s the sort of behavior that can strain any friendship, especially when the potential fallout is pretty damn immense.

So what do you do? Well to start with, I’d say jerk off. Horniness has a tendency to suck all the blood away from your brain and suddenly your balls get veto power over the rest of your decision-making process. It’s a lot harder for your dick to make stupid decisions when your brain isn’t floating in a pool of sexual frustration.

Next, you lay down some boundaries with L. You tell her, “Hey, I don’t know what was up with the other night, but that made me really uncomfortable. I like you, but you’re married to J and the way you were acting made me feel awkward around both of you. I don’t appreciate being teased and I don’t want to end up being part of a problem between the two of you.”

Now the ball’s in her court. She may pretend she doesn’t remember; you pretend to believe her. Same with if she says it was a joke, you were mistaken or any other variation of “it never happened.” Just go with it. Being “right” in this case is less important in making it clear that you don’t appreciate being put in that position.

And then… let it drop. If she’s as cool a person as you say, she’ll realize a line was nearly crossed and be careful not to do it again. If she gets a little buzzed and handsy again… well, put some distance between the two of you, make sure you’re not left alone together and try to avoid hanging out with her when alcohol is involved.

I realize what you want is incredibly powerful, especially when it drops into your lap and starts to wriggle. In other circumstances, I’d tell you to go for it. And who knows, maybe in the future circumstances will be different. But right now, if you did give in, you’d regret it far more than you’d enjoy it. Trust me: I have been there, done that and printed the t-shirts.

As hard (fnar) as it is, maintaining some boundaries is the best thing you can do here.

Good luck.

Have you had to say no when you really didn’t want to? Have you ever walked into a dating mistake with your eyes open? Share your thoughts and experiences in the comments and we’ll be back in two weeks with more of your dating 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.

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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 dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is out now from Amazon, iTunes and everywhere fine books are sold 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.

Top image via Shutterstock.