My Girlfriend’s Best Friend is Jealous Of Us And It’s Hurting Our Relationship!

Estimated reading time: 21 minutes

Dear Dr. NerdLove: Medium-time reader, first time writer.

I have a weird relationship problem and I’m not sure how to handle it without causing more problems. I’ve been dating my girlfriend (let’s call her “Amanda”) for a while now, and for the most part, things are great. But there’s one thing that’s been bothering me, and it’s starting to eat away at the trust I’m trying so hard to build.

It’s her best friend “Hugo”, a guy she’s known for years.

According to her, they’ve never dated, never hooked up, and she swears it’s purely platonic. I believe her, but I don’t know if HE does, if you understand my meaning. I know he was her friend before she and I got together and I’m trying to respect that, but the way he acts around me makes it really hard.

Hugo’s never outright hostile in ways that I could point to. It always seems to skirt right at the edge of passive-aggressive with just enough deniability that if I make a stink about it, I look like a paranoid asshole. Instead, there’s always this low-key tension. He constantly makes little digs at me — sarcastic comments, passive-aggressive jokes, stuff that makes me look bad in front of her. I don’t know if he’s hoping I’ll hit him or just start yelling, I swear that he’s trying to provoke me into starting an actual fight. He brings up reasons why we’re “obviously” going to have to break up (and then swears he’s joking, can’t we take a joke?) or questions my loyalty or interest in Amanda in these subtle, manipulative ways. And anytime Amanda and I go through a rough patch – nothing serious, just the usual sort of friction that comes up in relationships – or even just have a disagreement, he’s right there whispering doubt into her ear.

I can’t prove it, but I’m also more than a little convinced that he’s either tried to catfish me or got other friends to try. I’ve had a few DMs from people on my Instagram that seem unusually flirty, but different enough that I don’t think that it’s one of those weird “oh wrong number but whats your name” love scams. And writing it out like that makes me feel like I’m taking crazy pills.

I’m trying my best not to be the stereotype of the possessive jealous boyfriend, but I am well and truly convinced he doesn’t just dislike me, he’s got a thing for Amanda and he sees me as competition. I’m trying not to take the bait, but the needling is constant, and it’s always on the same theme about me and Amanda. I know what I sound like when I write this out but I really feel like he thinks he’s playing the long game, waiting for a chance to wedge himself between us.

I don’t want to be the guy who says, “You can’t be friends with him.” That’s not fair to her, and honestly, I know it would probably backfire. I feel like that’s precisely what he’s hoping for. But I also don’t want to sit back and watch someone slowly poison our relationship from the inside.

How do I protect what we have without looking like I’m trying to control her friendships? How do I handle a situation where I know someone’s intentions aren’t as innocent as they pretend to be?

Appreciate your help,
It’s Not Paranoia If They’re Out To Get You

I’m going to say something that I don’t say very often: I think you may be on to something, INPITOTGY. I think you may be a little jealous, but I don’t think it’s unfounded.

Because, back in my bad old days? I was that guy. And to be honest, I was good at this. To be clear: I’m not proud of the I used to be, and it never worked the way I ultimately hoped. In fact, it once nearly blew up in my face when the woman I was trying to get with called me out for it and (rightly) read me for filth over it. I was never a full-bore Iago or anything, but I was very good at being a habitual line-stepper, giving just enough to throw a little sand in the gears or drip enough poison in someone’s ear to make them have doubts.

To add to this: there’s an actual subset of the dating coach/PUA-redpill/manosphere industry that focuses on how to undermine women’s relationships and convince them to dump their boyfriends or cheat on them with you instead. Back in the long-long ago, when I was still part of the PUA community, people were trading what they called “boyfriend destroyers”, routines and strategies for how to handle women who already had partners.

Most of them didn’t work – I refer you to the “nearly blew up in my face” I mentioned earlier – but the desire was there and where there’s an opening in the market, there will be people who try to fill it.

So yes, I don’t think you’re crazy. I think you’re dealing with a self-declared Nice GuyTM who thinks that you’re the only thing standing between him and his Oneitis. Never mind that, y’know, she isn’t interested in him; he’s hoping that he can wear her down or eventually catch her in a moment of weakness.

So, the obvious question is: what do you do about this? As you point out, if he’s being a habitual line-stepper but he’s careful not to do anything overt enough to lose any plausible deniability, then you run the risk of coming off as jealous and possessive. That’s precisely what he’s hoping for; he wants you to be the irrational, jealous boyfriend. He wants to trade on the “I was her friend first” aspect of their relationship. It’s a point of pride to him, a “I’ve seen them come and go, and I’m still here”. That longevity doesn’t overcome everything, but it definitely counts for a lot.

Well, the most obvious answer is that you need to not take the bait. He’s hoping for a “it’s him or me” ultimatum, especially if he can pretend to be the victim. Even just calling him out on it privately is going to make it easier for him to play the “I’m just a little guy!” game. As frustrating as it is, you are in a position where you’re going to be perceived as having more social cachet and power than him, so even if you’re in the right, there’s the very real risk of looking like you’re punching down (metaphorically). As much as it sucks, you are stuck having to take his shit with a smile.

But please note that this isn’t the same thing as doing nothing. Yeah, he’s running a game on you. Yeah, knowing he’s running a game on you doesn’t make it easier. But nobody said you had to play according to his rules. In fact, you’re in a position where you can make it backfire on him.

Here’s the thing: his ultimate goal is to change how Amanda sees you and thinks about you – whether by undermining you in her eyes, or provoking a reaction out of you that would make her angry enough to dump you. As someone who’s run this game before, I can tell you exactly where the weak points are.

The first is that this requires that you feel threatened by him. The way he needles at you is intended to prick your ego, but also to make you worry that it’s working on Amanda. If he can’t manage either, this part of his plot fails.

So start by flipping the script on him. He needs you to be the brittle, jealous bro. Go the opposite direction: be the himbo instead. Rather than treating him like a threat, treat him like a buddy. Now I don’t mean that you need to really be friends with him; that would be preferable, but it seems like he’s determined to play the asshole.  By being friendly and helpful, you disarm any accusations of your being threatened or jealous of him. It’s hard to say “hey this guy’s a jealous, controlling loser” when you’re being friendly, inviting him to grab beers and generally being a human-shaped golden retriever when he’s around.  Playing along with the needling – the classic “agree and amplify”, where you functionally “yes and” whatever he starts with and take it to an absurd level – robs his put-downs and negs of power and makes you into someone who’s not just self-aware, but confident enough to joke about yourself. It also makes him look like a jerk if he keeps trying to pick a fight and you treat it like it’s all great fun. Doubly so if you don’t zing him back, or do so in a way that isn’t actually mean or insulting. It’s like trying to punch a sponge; when there’s no resistance or hard surfaces, everything just sinks in without real impact.

You can even do things like offer to help him meet some lovely ladies or – even better – say you’ll set him up. “Hey, have I told you about my friend $_NAME? She broke up with her asshole boyfriend last month and I think you and she would get along great! How about I get you two together and we see what happens?”

It’s going to be very hard for Hugo to refuse this without being obvious and it fucks with the narrative he’s trying to build. It also could lead to him meeting someone else and finally letting go of his attempt to monopolize Amanda, which means everyone‘s a winner.

The other weak point is that he wants to sew division between you and Amanda. This is a risky play, especially if you and Amanda are already pretty solid; the odds of it backfiring are high, especially if he ends up tipping his hand too much. So your play is to frustrate him until he makes a mistake.

There are a couple ways guys like him will try to bust up a relationship. One is to create jealousy plotlines, where he tries to imply that you’re not faithful to her. The other is to try undermine you by making you look stupid, uncool or otherwise work against your appeal to her. In both cases, this requires a level of emotional intelligence on his part, but it also requires that there be enough room or him to drive a wedge in. The way you beat it is actually simple: you behave the way you did at the start of the relationship. You don’t want to make a sudden 180 – that’s the sort of thing that can come across as “wait, are you trying to compensate for something?” – but you do want to start to ramp up the good-boyfriend behavior.

I’m a big believer in “the way you won them is the way you keep them”; that is, the behavior that helped you partner fall for you is precisely how you keep the relationship strong and vibrant. So returning to the behaviors from the start of your relationship with Amanda, when everything was fresh and new, is precisely what helps strengthen it. Remember the days when you would do little things out of the blue, simply because they made her smile? Or the level of effort you were making when planning dates and getting together with her? Remember the random flirting and compliments and affection? Bringing that back is the sort of thing that makes Amanda feel good without coming off as being performative or like you’re trying to distract her from a mistake you made. It reminds her of why you two fell for each other in the first place and it will just make her happy.

It’s hard to have doubts in a relationship when your partner is making you feel appreciated and desired. It’s hard to sell “he’s not good for you” or “I bet he’s trying to get someone on the side” when you’re showing up after she had a long day at work with take-out and a cozy movie queued up on Netflix so she can relax and de-stress.

Bringing that happy-boyfriend energy makes him look small and petty and strengthens your connection with Amanda. And, at some point, you can say “hey, can I something crazy? You know him better than I do, but I would swear  that Hugo’s got a crush on you.”  The important thing is that you treat this as being cute, not threatening or – and this is important – absurd. You do not want to talk Hugo down. You aren’t trying to imply that he’s sad, pathetic or delusional for thinking he has a chance, and you absolutely don’t want to imply that he’s Nice Guy-ing her. If anything, you’re a little worried that he’s going  to get hurt, because he doesn’t deserve that.  You play it as though you’re picking up on a faint vibe and let Amanda take it from there. You follow her lead – if she doubts it, then all you need to say is “I dunno, you’re pretty crush-able” and make it more about how awesome Amanda is. If she asks if you’re jealous, you go with the “agree and amplify” routine – you’re either about to go Big Moose on him (with appropriate levels of “daaaaaah, stay away from my goil” levels of oafishness) or “Hey, I’m never going to stand in the way of true love!” If she thinks you’re wrong, then you nod and say “…yeah, probably. I just assume everyone likes you the way I do because it seems absurd to me that they wouldn’t, because you’re pretty damn special.”

Remember that part of the point is that you are agreeing that Amanda knows him better than you do, so you ultimately agree with her. And then you drop it, while continuing to be the awesome boyfriend you are. And I do mean continuing; you don’t drop things once Hugo’s no longer an active problem. Yes, you’re trying to handle a guy who’s attempting to interfere with your relationship, but continuing to treat your girlfriend like you just started dating strengthens your relationship overall. This ends up creating a win-win situation for you. Not only does Hugo get to flail impotently, but your relationship with Amanda improves because of it.

It’s an annoying situation, to be sure, and I understand that you’re frustrated. By being the better man and boyfriend, you ultimately benefit and Hugo either gives up and grows up, or else he’ll fuck up big enough for Amanda to call him on it. Either way: you and Amanda win.

Good luck.

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Dear Dr. NerdLove:

I am a 31-year-old man from Australia who has had ADHD their entire life. I am what most people would consider a relatively handsome looking person. I moved to the capital city of my state about 6 years ago and started using dating apps. Coming from a small country town, I had never really approached woman and never had a long-term relationship. The only times I have been with women since moving to the capital city was when they initiated it with me through friends or something. Anyways, I found a fair amount of success on dating apps, basically dating and having sex with a new girl every month.

After about 3 years of this dating apps use on and off, I finally decided to settle down with one girl who I really like at the time. I was 29 and she was 19 (yeah yikes I know). While she was super young, she had been through a lot of life already and was very mature for her age. She had lived in 5 countries and her mother passed away when she was younger. She lives with her alcoholic father and two brothers.

Our relationship was great, everything flowed so effortlessly, she would come over whenever I was free and make all her free time in her schedule available for me. I really loved hanging out with her, we had the same taste in so many different types of music, same sense of humor, enjoyed the same food. She would be constantly be giggling to herself at all the stupid shit I would say and do and it would just brighten my day.

We were having sex consistently up until about the 1-year mark. After this point, I think both of us kind of let ourselves go a bit as she had put on a little bit of weight and I had lost a bit of muscle as I had stopped going to the gym as much. I was her first sexual partner so I pretty much had to initiate everything as she didn’t know how. Even after 1-2 years, I was still the initiator and she just never really learned how to be sexy and flirty and to create a vibe for sex. I found myself being attracted to other women more and watching porn more (I was still watching porn a little bit during our relationship but not as much as I was towards the end). After almost 2 years, I was flirting with the idea of being single again and longing for experiencing new women every month (grass is greener effect?)

I still thought she was very cute and we were basically each other’s best friend. But I started to see her be a bit more down and sadder as time went on and maybe that was her subconscious realization of me not being as attracted? A few months ago, she sent the first text to me about how I seemed distant and asking if we are okay. A couple of weeks ago she sent another text when I was away for work asking the same thing and saying that she loves me very much but she has started to feel like she is not enough for me and it’s made her feel very vulnerable. This final text lead me to send a text suggesting that we should break up. Once I got back from work, I invited her over one last time to discuss it in person and boy was I not prepared for these emotions. She basically sobbed in my arms all night, heart racing, trying to come with every idea why we should stay together and that she thought things were moving along and we were going to move in together soon and get a cat. She left me some letters that she had written when we had just begun our relationship and these made me tear up for several days. Even now, two weeks later and having initiated a no contact period, I’m still tearing up over it. I have started to see a therapist and he has given me some questions to consider about what I want in a relationship etc. honestly? I don’t know what I want. I know that I want something like what I just had that was nice! So nice…

Do you think I jumped the gun to quickly and maybe should have talked to her about things? My ADHD makes me super impulsive and I thought I was doing the right thing for both of us at the time. But man, the thought of never having her in my life again feels like something has been torn out of me.

Jumped Too Soon

Welp, sounds like it’s time for the Chair Leg of Truth.

Let me ask you something JTS: what were you hoping for when you decided to break up with her? Were you missing the early days of the relationship when everything was fresh and new and effortless? Were you thinking that you could do better and find someone who wasn’t going to be as passive a partner in bed? Or did you honestly think this relationship came to its natural conclusion and it was time to call it?

I ask because, quite frankly, I’m not really seeing a problem here that you didn’t create. It seems to me like, you fucked this one up for no good reason, super-chief.

I’m sympathetic to folks who maybe aren’t used to the ebb and flow of desire in long-term relationships, especially once the NRE stage is over and the desire for novelty starts to reassert itself. But there’s “relationships aren’t necessarily going to be as wild and crazy as the first six month to a year were AND THAT’S OK” and then there’s “Well, I’m finding myself attracted to other people so clearly it’s time to blow up this relationship.” And it seems like you went with the latter option.

And to be fair: there are people who need novelty and who lose interest in their partners after a certain amount of time. But those are people who are best served by leaning into that tendency and not expecting a lifelong, monogamous commitment; that way lies a lot of unnecessary heartbreak.

Being attracted to other women doesn’t mean anything other than that you’re a primate with a sex drive. Humans are a novelty-seeking species, and that desire for novelty includes sexual novelty. We get a burst of dopamine and oxytocin during sex, especially with a new partner. But humans are endlessly adaptable and what’s new and novel eventually becomes our status-quo, no matter what it is, and we don’t get the same happy-brain-juice burst from sleeping with the same person; if we sleep with someone new, then suddenly the pleasure chemical bursts ramp up again.

All of which is to say that the desire for novelty is always going to be A Thing; it’s part of being human and the way that no one person can be all things to us. Part of why people like porn is that it’s a way of getting that desire for novelty met without actually seeking out a new partner. Unless you were actively avoiding having sex with your girlfriend in order to jerk it to porn, that wasn’t a sign that anything was seriously wrong.

And to be perfectly honest, some of the issues you talked about were easily fixable; you just had to open your mouth and say what you needed. There was no reason you couldn’t say “hey, you know what I’d love? I’d love for you to take the lead in bed on occasion” or “You know what might be fun? I’d like you to seduce me…” That could then lead to a discussion about some of the things you’d like to try or that she could do – things that could lead to some new and interesting adventures for the two of you. You could even make a game of it, use this as a basis for exploring fantasies or taking a sort of service-sub approach where you coach her at first on the sort of behavior you wanted to see.

It’s not saying anything about it that was the problem. Your girlfriend wasn’t a mind-reader; if you don’t tell her what you’d like her to try or do differently, she’s not going to magically intuit it or divine it out of the used coffee grounds in the morning.

More to the point, her seeming sad and down probably had a lot to do with the way you were behaving. You were acting like you weren’t attracted to her anymore and you were being distant and it seems like you never actually tried to address any of these things. I’m not surprised that she was worried that something was wrong in a way she couldn’t put her finger on; that’s precisely how you were acting. She was picking up on the vibe you were putting out there, and she was getting upset.

When she was asking about it, what she was asking for was reassurance and for you to at least communicate with her about it. And you didn’t.

Could she have been a little more proactive in saying “hey, what’s wrong?” or “I’m getting a feeling from you and I want to talk about it?” Sure… but also she was 19 when you met and this was her first serious relationship. I’m not going to hit you too hard about the ages because I think a lot of the age-gap discourse has absolutely lost the plot, but you are older and presumably more mature than her. What’s understandable for someone in their late teens and early 20s is a hell of a lot less reasonable for someone who’s hit his 30s.

And quite frankly, I think the way you handled the break up made things worse. There’s not really a good way to end a relationship, but there’s such a thing as not causing unnecessary pain… which is precisely what you did. In an ideal world, a break up – especially where you aren’t living together and aren’t having to do things like untangle your finances – works best if you rip the bandage off; the longer the process takes, the worse it hurts. The short sharp pain is awful, but dragging it out is worse. And initiating the break up over text, while you were away and finalizing it later was just needlessly cruel. All that did was give her more time to soak in what was about to happen until you called her over to administer the final blow.

You sure as shit don’t sound like you were even sure you wanted this. I’m not surprised that you were shocked at how things went, but I honestly wonder how you thought it was going to go. Did you think this was going to be a simple and unemotional discussion, ending with her saying “yeah, you’re right, welp, be seeing you”? Because if that’s the case, then way to misread the room dude. Like I said: she already was signaling that she was feeling you pulling away and was worried. This was always going to hurt her. The way you did it just made it worse.

To drag this back to the question you asked: it doesn’t matter if I think you made a mistake. It sounds to me like you think you made a mistake; I’m just not sure if you’re hoping I’m going to tell you that you made the right choice or not. And I’m not going to tell you, in this case. I think you’re the one who has to decide that.

To be clear: I don’t think this relationship was going to last the ages. First relationships often don’t, but then again, all relationships end until one doesn’t. But the fact that this may not have been your last relationship ever doesn’t make blowing it up for stupid reasons hurt less.

So now, you have to be the one to decide what happens next. You clearly have regrets. You are going to have to decide whether you miss your ex specifically, or if you miss the way having a girlfriend made you feel. If you’re going to let this go, then congratulations: this is a learning experience for you. The regret and pain you’re feeling should teach you to be more mindful of what you’re doing next time.

If you’re going to try to walk this back, then you better be ready to do some serious groveling and apologizing for being an idiot. And you’d better be ready for things to be strained while you both try to reconnect and find a new equilibrium – something that may take a damned long time, considering.

And here’s the other thing: you’re going to have to ask yourself whether those “problems” you had were problems and if they’re fixable. Because unless you can get to the bottom of what you thought went wrong and decide whether they’re fixable – if they were problems at all – then calling her up, telling her you made a mistake and begging her forgiveness and a second chance is just going to lead to the 12” dance remix of your first break up – just faster and more intense.

But whatever you decide, you better be very sure about it. Because, quite frankly, if you try to get back with her and you just make the same mistakes over again? You’re going to cause even more unnecessary pain, and you’re going to deserve every moment of guilt and remorse you get from it.