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Alright /adv/, help me figure this out: Me and my best friend

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Alright /adv/, help me figure this out:

Me and my best friend started working for her (single) mother's company almost a year ago. She's the executive of this company, and while she's a ruthless boss she can be pretty nice and I have no complaints about her, even though she and my best friend have a really complicated relationship.

There's this guy, he's basically her assistant, and we are constantly playing/going at each other and it usually ends up in friendly flirting. My boss noticed this and she playfully asks about him and if we're dating already, stuff like that. During the Company's Christmas dinner we went to this balcony-like room for a smoke and we were having a good time until our boss walked in on us. That's when it got really weird:
>Well(dramatic pause), I can see you two are having fun (imagine this in the most conceited tone possible)
>Yea. We are.
They both stared at each other for too long and that's when I realized something was off. She asked him to come help her with something and he apologized and left.

Today I had to back to work and I avoided him like the plague. My best friend noticed this and I told her I didn't want to talk about it (mainly because I'd have to imply I suspect her mom's fucking him) but she vented to me instead about how her mom had done nothing but complain about him after the Christmas dinner and how she should get a new assistant all of a sudden.

He texted me twice today, one asking if I was ok and the second asking if I was mad at him.
Should I even bother replying? I really fucking like him but this is such an awkward situation

You absolutely should reply. You have no reason to believe he did anything wrong, at most you can reasonably believe your boss is a jealous bitch.
But what if he did? Looking back there were so many flags anyone could have easily ignored. I just have that gut feeling telling me they have a thing going on.

I don't know what these flags really are, though. Could you give examples?

If he didn't, you're just punishing him for nothing.
A few months back we talked about relationships. I vented about breaking up with my ex and getting off a long relationship with a really manipulative/jealous person and basically he said something like he knew what it was like to feel stuck with a person you don't love anymore and how hard it is to leave everything behind.

My boss's weird interest in us, how she liked to humiliate him in front of me (basically busting his balls. Pun intended).

Also I remember my best friend complaining how she'd pay him way more attention to him than her own daughter, but this was even earlier like in February.

Man, it seems like he was in a relationship with her and she's being a bitch ex butting into his business. If he IS in a relationship with her, which it seems like he's not, he may feel stuck.

Personally I'd reassure him that things are cool between you two and say something about her being weird towards him.
That's the thing, things are not ok between us. Don't I have the right to feel a little cheated on if he is fucking her?
Should I just ask him now via text?

Not /really/. You guys aren't dating and some people flirt without meaning to lead someone on. It's not SUPER common, but it happens.

If you ask him out of the blue you're probably going to come across as paranoid and jealous.
I agree with you but I have no idea how to bring it up. I really want to ask him and I know we weren't in a relationship but I feel mad about the whole thing, almost disgusted because it's her.
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My advice for clearing the air with someone you consider a friend is to advance as if you aren't questioning their motives. I know it sounds naive, but you are supposed to trust a friend.

Simply put: just ask if he's seeing/dating/fucking someone. Accept his answer. If you can't do that, you're just pretending to be friends anyway.

Just sort of point out that your boss is being weird towards both you guys and ask if he knows why.
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I want to ask him directly so badly

Repress that urge, because you asked well.
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UH. Am I reading this right. Avoiding me "TOO"?

It certainly looks like it. At least he isn't following what she's saying, if she really did tell him to avoid you.
Wow ok. He basically confirmed it. They are a thing. I don't even feel like replying to him anymore.
Advice from a guy:

If you want to date this guy, you need to stop dancing around the subject and get some goddamn closure.

Tell him you're interested in him, but he needs to explain what's going on with your boss before you'll follow through. Someone did something. If he continues to give you vague answers, walk away from him. He's dishonest.

Alrighty, just tell him good night and stop replying. It's non-bitchy but final. Sorry man.
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I don't even know
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Now it's time for you to get over yourself. He was enjoying your attention; that's human. Everyone has done this and everyone has been on the other end of it. There's no reason you cannot be friends, and, if he resolves the situation, pursue something more in the future.
Yea I guess. Just feeling heart broken. We're still talking and he's saying he likes me etc but I'm too hurt right now. Sucks I have to see these people on a daily basis.
Have you fucking asked him direvtly if they fucked and where in that kind of relationship? Aaaaw you are hurt uh? Poor little thing, whag are you going to do now? Your world is literally ending.
Jesus. Fucking. Christ.
The guy is literally telling you he almost ended up homeless and he has a fucking scar probably from his teenage years.

You know what? He will be better without you. I'm not saying you shouldn't be mad because you don't know if they actually had something deep going on and he flirted with you but it's not like the guy is your bf man. What is wrong with you? Have some decency and if you want to feel bad then ask him for space for a while to think.
And fucking ask directly if he and your boss had something. Directly OP directly
>Aaaaw you are hurt uh?
Calm down dude. I'm not saying I'm going to be mad at him for being used like this, I'm just thrown back by the whole situation.

And yea they've basically been having a relationship, though he's been trying to get out of it from what he's telling me.
It'll be fine. I had something similar happen recently. New co-worker seemed to show a lot of interest in me, but circumstances kept me from pursuing immediately. We start hanging out more a few weeks later, enough for people to start asking questions. She tells me she's uncomfortable with that because she started dating someone on a different shift. I was disappointed that she hadn't mentioned it sooner since I believed I was being very obvious about my interest, but she's consistently had my back so I didn't let it get in the way of our friendship.
Sounds like he's in a really bad situation to be honest, but I guess your fee fees are the important thing here.
Well then if he has actually said that then you can be offended. Thing is thia guy is in trouble and it would be on his best interests to quit the job and you should also understand why he did what he did. Doesn't mean you have to do anything.

You just got bad luck but the guy's had it worse than anyone in this situation. Just don't make it harder for him. I'd recommend not to get involved with him if he is going to keep working there. At least. Until he has his shit straight but I wouldn't.

The thing is, don't be harsh on him. That's what creates bitter persons
Just don't make a new bitter person for the world
The world thanks you
Such is life
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I'm not harsh, it's not his fault. I'm trying to tell him I'm going to help him but he's kind of freaking out

I agree. This guy is in a bad situation and if what he says is true, he's being blackmailed. HR handles a lot of stuff that isn't its business, but this is ONE THING THAT IS HR'S BUSINESS. He would be wise to go to the police and ask for advice on the situation.
He says he doesn't want HR involved. That it's his fault too. He says he'll quit his job at best. So fucked up.
Even if I leave my own job I'll still have to see our boss because of my best friend.

He's being coerced. He either needs to stand up for himself or consult HR.
We'll work on it. He's being all sappy now about how he feels about me, I think he's trying to change the subject because it's hard for him to talk about it. And probably because he's scared I'll bolt or something.

Or because he DOES care about you and he feels shitty about the situation.
Well, YEA, that too. Even though this is whole situation is horrible he's being so sweet.

I'd recommend not getting into anything romantic/dating right now at least. This guy seems to need a bit of help.
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Ye that's what I told him but we're being disgustingly cheesy right now.

Cute. Enjoy that.
Tell your boss you want to be her other sex-slave.
How old are all of you? The boss perhaps found your juvenile drama amusing and invigorating at first but has come to find it annoying and unprofessional.

You've gotten a job effectively out of nepotism and this woman's good grace, playing romeo & juliet in the workplace is stepping on her toes.
Lol this is probably the most accurate post. /adv/ tends to victimize the people in whatever story the OP is about, because they are used to victimizing their selves.
Thread posts: 41
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