I 30f have been friends with Julie 31f for nearly 10 years. Would have never known it originally but her family is loaded. Mountain house, a beach house in CA, paid for her tuition and her car. Julie was always very quiet about her privileges.

Her husband Kevin 29m was raised very blue-collar. He worked very hard, got his degree and paid for it, helped his family out. We get along very well, he and my partner are friends and, ultimately, they became part of our larger group of friends too.

A few years ago, Kevin got laid off because of the pandemic. After this, Kevin changed. He started to freelance (said it’s because he never wants to work for “the man” again). FWIW, Julie has a stable job and makes okay money… enough to make sure their mortgage and bills are paid but that’s about it. Occasionally MIL/FIL will cut them a check and gave them the down payment for their house. With Julie working and free money rolling in, Kevin has little incentive to work.

More often than not, Kevin will text everyone in the group chat about how he isn’t “feeling it” and doesn’t want to work so ends up playing video games (meaning he isn’t working or getting paid). That would be okay, but all Kevin does is talk about how he doesn’t have money and whines about how he doesn’t want to work, and how pissed he is that he and Julie don’t have the money to travel more. More often than not, it’s not uncommon for Kevin to be at the bar at three o’clock on a Wednesday to “get out of the house.”

Kevin legit gets nasty to others when they have to be home more than two weeks in a row because he says he’s “cooped up” while his wife and friends are working and then his sour attitude gets directed at everyone around him. This attitude has gotten worse and worse. Also keeping in mind they travel to her family homes multiple times a year and are often gone at least one-two weekendsa a month. Sometimes I just want to scream at the guy over his lack of unchecked privilege.

The issue I’m here to work through is Kevin has been pretty passive aggressive and gets pissed that his other friends can afford to go on trips. He also refuses to share in or celebrate friends milestones, like promotions. It’s pretty evident he’s depressive and jealous. He makes snide comments about friends who have the capability (and do) go on weekend trips or bigger vacations. We (his friends) will ask him how he is, he will answer (usually about how he doesn’t want to work or “just a wants to travel”) and never asks others how they’re doing. At one point he said the only job and the only way he’d feel happy/fulfilled is to be Anthony Bourdain.

If people try to include Kevin in on their milestones, he’s passive aggressive and will talk crap about everyone behind their backs. If they don’t include him on big news, he gets nasty and demands to know why they didn’t tell him (like buying a house or getting a puppy).

It just feels like he doesn’t get it. It seems like he believes we magically have money, and Kevin deserves it and his friends don’t. He believes he’s entitled to know every detail about his friends but he’s nasty when they share and nastier when they don’t. Example: A friend bought a new car after he got a promotion (he was still driving his car from college) and Kevin talked behind his back for weeks saying this friend blew his money on a new (USED) car.
Example: Kevin is upset one of our friends bought a house with his longtime girlfriend and they’re having a baby.
Example: We moved into a new place after my partner and I both got promotions and Kevin pestered us about how much we were paying in rent (I refused to tell him, it’s none of his business) but he looked it up anyway. He has since made passive aggressive comments about being in a different socioeconomic group.

He’s whiney and all is does is bitch to and about his friends. He is miserable to be around and doesn’t celebrate anyone’s accomplishments. He’s nasty to his friends when things aren’t going his way. If he’s not the one traveling or making money or succeeding, all he’s doing is judging those that are.

Kevin is so integrated into our lives (married to my best friend, friends with my husband, friends with our larger group of friends) that I can’t just cut him out. But I am so over this dudes petty behavior – no one can do right in his eyes and all he does is whine.

I feel it’s not my place to say anything to Julie about their marriage so I keep my mouth shut. However, Kevin has been nasty to me, my husband, all our friends because life isnt going his way is weighing on ALL of us. It feels like we’ve watched him spiral hoping he’d snap out of it, because this isn’t the Kevin weve all known through high school/college, and no one knew what to say or if it was even our place.

If I cut Kevin, I know I’ll lose Julie. If I ignore Kevin, I won’t hear the end of it from Kevin. If I call Kevin out, he can be very bullish (I know this from past experience).

I genuinely don’t know what to do for my sanity. But I’m worried about depression. And alcoholism. And just being a big plain jerk to people who love him.

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