He Slept With His Best Friend


Hey Meredith,

Longtime reader here. I’m in a rather messy predicament right now. I’ve been best friends with this guy, let’s call him Jason, for about seven years. We’re inseparable and we know each other inside and out. About three years ago Jason met his now husband, let’s call him Michael. Jason was just out of a long-term relationship when they met so I figured it was just a rebound, but things started to progress really quickly between them. Five months later, they were engaged. I like Michael, but it was evident from the very start of their relationship that they were going to have a lot of trouble.

As Jason’s best friend, I voiced my concern but I told him that I would support whatever decision he made as long as it would make him happy. Now that they’re married, everything has gone so far downhill that I can’t even properly explain it in this letter. They fight constantly because they rarely see eye to eye on anything. It’s gotten physical quite a few times, but Jason keeps going back for more. He doesn’t see how toxic and unhealthy this relationship is and he always ends up blaming himself in the end.

So now my main reason for writing this letter. Jason and I have always been unusually close,  so much so that almost everyone thinks we’re dating. We never once thought of each other sexually until very recently when a drunken night turned into us having sex. It didn’t stop there either. It happened again a couple of other times as well. It was very clear that the massive friendzone wall we’d built over the years was rapidly crumbling down. Feelings have now developed on both sides and it’s killing me a little. Before you guys get all judgmental, I fully realize what I did and I know that it’s not right, but I don’t care. I also realize that the odds of this working out in my favor are slim to none, so no need to reiterate that point. I just find myself thinking of him constantly.

My question is this: Over the seven years we’ve know each other, we’ve developed such a deep and personal relationship that this evolution seems natural. How do I even begin to go about dealing with this situation? I’ve tried to put some distance between us but it doesn’t work because we’re too close. I’ve also tried talking to him about it but we can never come up with a solution. I do know one thing for sure – no matter the outcome of this situation, his happiness comes before my own. I will make sure he’s happy one way or another.

Any constructive advice would be most welcome. Thanks, guys.

– Lost in Love


If you want a solid relationship – friendship or otherwise – you can’t put Jason’s happiness before your own. It’s impossible to be a good friend to him if you’re stuck in an unhealthy place because of him.

You say that you tried to keep your distance from Jason but that it didn’t work because you’re so close. My advice? Try again. I’m not saying that you have to end the friendship, but for now you need space to consider your own needs. You’re trying to help him navigate an abusive relationship while pining for him and imagining a future together. It’s time to get some perspective.

Let him know that you love him but that you need to take a break. Set some boundaries together so it’s clear this isn’t a punishment. Make sure he knows that he can call on other friends for help.

The thing is, even if the sex hadn’t happened and your relationship remained platonic, I’d probably suggest some space. It’s great to have a best friend who knows you inside and out, but if you’re truly inseparable, it’s hard for anyone else to get your attention.

Readers? Should he take space from Jason and if so, how much? What’s the goal here?

– Meredith

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