My (F30) best friend (M25) is secretly living a double life, and I'm also his boss. Where do I draw the line?
My best friend Mike dated a woman for 7 years. Let's call her Kay. During that relationship, he had a female best friend Jill. Kay always believed there were feelings between them, but Mike denied it. He would also come to work miserable, always, and always upset about his relationship. He confided separately in Jill and I about his relationship, and we both advised him to break up, though Jill was pushier about it.
During this time we needed to hire a new employee, and Mike suggested Jill, as she had a lot of experience in the field. I agreed to give her a shot, with the understanding that their relationship remain professional. They both agreed.
Eventually Kay and Mike broke up, and he started dating Jill shortly after. Within a month or 2 of dating Jill, things went south. Jill went from the fun "best friend" to a complete negative nancy, always complaining and upset/mad about everything and anything. Mike quickly realized the awesome "best friend type friendship" he had was gone and now he was more miserable than ever. Mike secretly sent his ex Kay, flowers, apologized, and continued talking to her behind Jills back. He told me all of this while drunk and I got very angry at him for 2 timing them and also dragging this dynamic into our workplace. I told him he needs to break up with Jill, and if he wants to get back together with Kay, he needs to tell her everything.
He eventually broke up with Jill, and got back together with Kay almost immediately. He did NOT, tell either woman, anything. Kay, has no idea that he EVER dated his best friend Jill, the woman she absolutely hated, and Jill has NO idea that he has been in any contact with Kay at ALL, since he broke up with her over a year ago (in her mind). He just celebrated his day "8 year anniversary" with Kay, despite dating and sleeping with Jill in between for over 5 months.
Now here's an even bigger issue. Jill, Mike, and I, all work together. EVERYONE at work has caught onto this dynamic, and it's affecting the workplace. Jill never stopped being bossy, negative, and getting upset about everything. Jill is always upset at Mike over something, and tries to hide it. They also have long private conversations during shifts, he always walks her out to her car where they will hug and cuddle on her car, they go out for food together after work and he pays for her, Jill will rub his back and hold his arm, and she is very possessive of him. He is always comforting her "moodiness" and his work ethic has become terrible. Jill is always distracting Mike at work, either in a good mood or bad mood, and he never sets any boundaries. Jill will STILL even come see Mike at work when she's not working, to spend time with him. ALL DAY. It makes everyone uncomfortable, especially because his girlfriend has no idea any of this is happening, but we all know the truth about the entire dynamic.
As their boss, this has become a workplace issue. Staff constantly notice the behaviour, ask questions, and feel uncomfortable. Multiple employees have confronted him and told him he needs to tell the truth and set boundaries, but he refuses. Morale is being affected because everyone feels like they're expected to keep a secret and watch inappropriate workplace dynamics play out, while also not knowing where to stand because no one wants to get involved in personal matters, yet it doesn't feel like this is just "personal" anymore.
From a workplace perspective, what would you do? / From a bestfriend perspective.. I just don't know.
Imo, you've been remiss as both a friend and a boss. As a friend, I'd be telling this pathetic jackass loser that I was disappointed in the lack of moral character he has continuously shown and stopped hanging out with him. Who would want to be friends with a jerk like this? He's not only ruining his own life, but literally everyone else around him as well.
I think it was also a bad call to consider hiring Jill at all. There was clearly drama there, and there was just no way that was ever going to work. It really doesn't sound like you've been proactive about managing the workplace either. At this point, due to your personal involvement in the situation, I think you need to loop in HR and legal and get their advice. At this point, HR might want to present a series of trainings to your entire team to avoid such a fuck up in the future.
Imo, Jill has created a toxic work environment from day 1. I have no idea what the quality of her work is, but sounds like she's slacking off during work hours and pressuring others do to the same when she doesn't even work there (any why hasn't she been kicked out when she's not on???). That feels like at least three good reasons to fire her right there.
As for Mike, even if he's a repugnant human being, he appears to have a good work history. It is probably most appropriate to put him on a performance improvement plan and see if he can prove that he can stop fucking shagging in the car like a teenager when he's supposed to be working and actually work during work hours instead of grab assing all the time.
But double check with your higher ups to make sure the company is covered and what the preferred set of actions is here. As well, maybe they'll realize you need more support and training and be proactive about setting that up. You are going to want to face this sooner rather than later because shit like this has a habit of blowing up pretty explosively, and you want to go to HR and your supervisor before things meltdown and become a crisis.
Also, depending on your place of work, if there's a uniform, if it's clear that he or Jill are employees there - upper management would probably be pissed to hear about their public facing behavior and how it could damage the company's reputation if people could potentially see employees slacking off in that manner during the workday. Whether fair or not, cuddling in your car parked on work property could 100% draw eyes. They're probably lucky nobody inclined to has complained to management for unprofessional behavior.
If work offers any sort of leadership or management classes: enroll. I get that it's not your job to babysit your employees emotionally, but holy shit. I hope there's a lot you've left out in correcting these two on their behavior because, yeah, that is 100% part of your job, as what they are doing is impacting everyone's work.
Finally, I'd suggest checking out Ask A Manager rather than relationship advice because what you have here is primarily a managerial issue, regardless of where you land on your relationship with Mike.
