Dating Best Friend's Boss

[Lamartine]

I recently started dating my best friend's boss. He's older, but he is a perfect personality fit for me.

 

Before accepting his invitation for our first date, I checked with my friend to make sure that she was not uncomfortable with it. I told her (and I meant it) that I would not go out with him if it made her at all uncomfortable. He apparently had a very similar conversation with her before asking me out. She gave her blessing to each of us individually.

 

Now, she will not accept any invitations to spend time with me (we used to send time together every day). My impression is that she is, in fact, angry at the situation. I am heartbroken. I miss my best friend desperately and don't even know for what to apologize. I don't want to have to choose between a man for whom I have very strong feelings and a friend.

 

What would you do in such a situation?

 

Thank you.

[Versacehottie]

Tough one. I'm not sure I have the exact answer. However, both you and your guy handled it perfectly and you shouldn't let her manipulate the situation. If she puts her needs above yours as this has played out so far IMO she is not a friend where things are balanced. She should be happy for you and even if it is awkward where she is worried that she can't be candid with you because you might run back to your bf aka her professional boss, there are ways to cope with that from both ends. Such as keep the conversations to more neutral subjects, like you wouldn't want to go too deep into discussing your romantic life with her bc that's her boss and she may want to be less candid about things that show her as irresponsible or potentially moving onto another job or venting about the one she has. Idk, it's time to move into a more mature friendship if she spent a lot of time venting about work and now feels like she cannot.

 

I would just keep trying to set up innocent lunches or low-key time to spend with her. If she doesn't voice her issue soon, you could bring it up. And say what you said here: you care about her and don't want to lose your friend and then ask her to express what is going on. I wonder if she could just be envious that you have a bf (rather than annoyed bc it's her boss)? Some girls do that. They want you to stay single while they are single. Sometimes it just time to evolve on from friendships that are not really balanced OR when put to the test (not that this really should be so major!) but the friends true colors come out. In other words, her friendship seems conditional. I'm tending to take your side because you can tell in your post that you handled it well & I remember from your other threads and posts that you are not really drama. In some cases, of course if the person that is you in this situation mishandled things, your friend could be in the right. But i don't get the sense that is what is going on here. Don't let her manipulate you. Good luck

[Lamartine]

Thank you so much! I hadn't thought o the jealously angle. She's quite desperate to find a boyfriend an its upset when random guys from Tindr she invites over for drinks don't want to date her. That is a distinct probability.

[Versacehottie]

Thank you so much! I hadn't thought o the jealously angle. She's quite desperate to find a boyfriend an its upset when random guys from Tindr she invites over for drinks don't want to date her. That is a distinct probability.

 

This is super common. I have seen it many times (i have a huge group of friends and while they are great people i've seen it happen over bf situation like yours, better clothes, lifestyle, body, job opportunities, other possessions, successful relationships with mutual gfs that seem to like you better or come easier to you; i know I have a good friend group but bc it's so common that i've seen it in many other groups of friends). It's just the kind of person who doesn't want to see you move onto your dreams if they are left behind or didn't get there first. Or they like to be the "best" or included and caught up with every milestone that other people reach. Instead of seeing it as they are probably close to reaching it as well and should be happy for their friend. And they worry that they will be left behind as the only single one if you are coupled up.

 

It's still concerning because unless it's minor blip of adjustment time, these are the kind of people who like you around only if you are kind of "less" than them and they get to shine at your expense always. If she is your real friend, she should hang in there with you as a friend and be happy for you, even if your relationship changes some & she needs to find new single friends to hang out with for that part of friendship. I just guessing this is the other possibility and now that you've given more info about her dating failures that makes sense. It might be a combination with a little jealousy about the boss because that implies he has some status/more financial means than another guy closer to maybe both your ages, level. Plus if she really can't get her own dating sh*t together it probably really hurts her (irrational but it's how she perceives it). She sounds just bitter. I don't think it will go away anytime soon (unless you break up with the bf). Anyway sometimes the ultimate conclusion of these kind of situations is that you are forced to realize you probably needed some distance from this person anyway if you really look at your friendship history. I hope I'm wrong or that she is not on the extreme end of it. Good luck

[lovephule]

If she hasn't distanced herself every time you've dated someone new I'd lean more towards her being weirded out / feeling like the situation is too close for comfort.

[preraph]

I hope you and the boss aren't talking about her and then he's commenting on it, because that's what I suspect. But it could just be that she no way wants to get in the middle of listening to either one of you talk about each other.

[Versacehottie]

I hope you and the boss aren't talking about her and then he's commenting on it, because that's what I suspect. But it could just be that she no way wants to get in the middle of listening to either one of you talk about each other.

 

I don't necessarily suspect that's what's happening, though, it could be. I do think it's what the friend is worried about though if it is strictly about the new relationship pertaining to it being with her boss.

 

If it's just envy in general, then the friend just wants to be "winning" or perceives herself with kind of low self esteem as left behind and pathetic a bit and is throwing a tantrum of sorts

[d0nnivain]

Do you want her friendship back enough to dump her boss? If not, try to realize that this is more about her that you. You took the high road & asked for her permission. She said it was OK. Now she's pouting. So she lied to you about being OK with you dating her boss & now she's acting out. That's not fair to you. She should have just told you up front she was against it.

 

On the one hand she may have been trying to be a good friend by keeping quiet about her objections . . . sort of being politically correct because she felt like she had to.

 

Give her some more time. Maybe when she realized your dates don't effect her work life she will come around. It may have less to do with you then some desire on her part to avoid mixing work & pleasure. She kinda had worlds collide here.

[BaileyB]

I understand your frustration because you both asked for her approval and she did not say anything to indicate that it would be a problem. It's not exactly fair for her to be upset when she had the opportunity to voice her concern, and she failed to do that.

 

However, if I'm being completely honest, I would never consider dating my best friend's boss. It's just not going to happen... It breaks the girlfriend code - just as I would never consider dating her ex-boyfriend, I would never date her boss. It's too high risk for things to go wrong, and I wouldn't want to loose either the job, or the friendship.

[2much4]

I'd leave her alone for a few weeks. If my best friend started dating my boss it would creep me out quite a bit and I guess I'd need some time to wrap my head around it. She'll come around.

[Popsicle]

It's too close for comfort for her.

[Keats]

Yes you are posing as a future possible threat and complication to her career and professional life.

 

If things go horribly wrong with you and this man, both you and this man should keep her out of it and treat her like a stranger in the matter.

 

That is how you will have to treat her, regards your relationship issues, to ensure her work environment isn't affected.

 

Looks like she already knows that, and is making herself a stranger rather than relying on you to treat her that way, when things go wrong. She knows when things go wrong, you won't be thinking about her, you'll be thinking about yourselves.

 

Besides, the friendship might be void now, if you can't even talk about relationships no more.

Edited March 22, 2018 by Keats

[act00]

Of course she didn't tell either of you not to pursue a relationship. Especially not her boss. I think it's too close for comfort and I wouldn't want my friend to date my boss, but I wouldn't stand in the way of it either. I wouldn't say that she's not allowed to pursue a relationship. I would, however, distance myself. She doesn't need you talking about her to her boss, if she complains about work issues, boss issues, coworker issues, and of course her personal life. She doesn't want her boss in on it. She has no control over what you might say and how he might interpret or perceive it. She doesn't want to know things about her boss outside of the work place either.

 

To me, it sounds like she's creating a boundary - keep her personal life and professional life separate. She doesn't want to be involved. She doesn't want to hear how he's being a jerk or that you bumped uglies with her boss or any of those things...this is her job and her boss.

 

It's not always a good idea to date a coworker or a superior for that matter, and this extends to personal relationships...her best friend is banging the boss...and do other coworkers know about this? Will her best friend being involved with the boss be an issue among peers and superiors? Will her own job be affected because of a nasty breakup or that you talked with him about her some antics over the weekend you and your friend participated in?

 

To me, she's separating herself from this romance and keeping her professional life and personal life separate. Your friendship has shifted, and maybe down the line things can get back to normal, but right now, she needs this degree of separation.

[Lamartine]

Just to be clear, I would never discuss my friend with her boss. I can’t discuss him with her either, since she won’t see me.

 

And she certainly could have told me not to do it. She means quite a lot to me, and I would never have gone for that first drink with him if she told me it made her uncomfortable. It never occurred to me that she may have thought she couldn’t be honest with me one on one.

 

That said, I do understand where y’all are coming from.

 

I hope I don’t have to write her off completely. She’s one of the best I’ve ever had. She swears via text that she is not angry, but she refuses to see me.

 

I wish she had just told me the truth.

 

I found out something big last night: my boss thinks that my friend has a little crush on him. The two of them are very close friends. He, however, does not find her attractive.

[kgcolonel]

Here are a couple of other possibilities:

 

1. One doesn't always know how they'd feel in a situation until they're actually in the situation. This cold be the case for her.

 

2. She may feel that she needs to take a step back due to the relationship you have with your boss, she's not necessarily mad but feels that the friendship was either changed or compromised by the relationship.

 

Personally, I think the guy is full of himself by sharing that HE thinks she may have a crush on him....this is a major red flag and in no way helpful....just my opinion.

[Lamartine]

Good points all the way around. The three of us used to hang out as friends all the time. I didn’t really see why this should change. She, however, may have begun to feel awkward despite her belief otherwise. He wants me to make peace with her so that the social group doesn’t change. I don’t know how to do it, though.

[BaileyB]

You used to hang out with your boss as friends?

 

I don't know that their is much you can do. You can either end the relationship, or lay low for a while and give her some time - recognizing that she may never warm to the idea.

[lovephule]

Good points all the way around. The three of us used to hang out as friends all the time. I didn’t really see why this should change. She, however, may have begun to feel awkward despite her belief otherwise. He wants me to make peace with her so that the social group doesn’t change. I don’t know how to do it, though.

 

You're looking to unscramble an egg here. The more you write the more it looks like distance is the only sensible option for this woman.

[Versacehottie]

Just to be clear, I would never discuss my friend with her boss. I can’t discuss him with her either, since she won’t see me.

 

And she certainly could have told me not to do it. She means quite a lot to me, and I would never have gone for that first drink with him if she told me it made her uncomfortable. It never occurred to me that she may have thought she couldn’t be honest with me one on one.

 

That said, I do understand where y’all are coming from.

 

I hope I don’t have to write her off completely. She’s one of the best I’ve ever had. She swears via text that she is not angry, but she refuses to see me.

 

I wish she had just told me the truth.

 

I found out something big last night: my boss thinks that my friend has a little crush on him. The two of them are very close friends. He, however, does not find her attractive.

 

I thought that it was possible she may have a crush on him and that it's that you got what she wanted. It was a possibility. I do think that's very possible so she just feels like everyone else, or you, always get what they want (with guys, perhaps other things). That IS a common dynamic among women. Haha I didn't want to plant the seed though.

 

There's one thing too on your friend's side of the matter is that if other co-workers know her best friend is dating her boss, it changes her work dynamic too. Where the others may think she is getting favoritism, etc. In a way, it puts her in a position she wishes she was never dealt. So on that I feel her. As I understand it, you don't work at the same place, right? And you met the boss through her. Often when friend groups are overlapped this kind of stuff happens. Someone steals what used to be your girl friend or starts a relationship with someone that was in THEIR group that they introduced you too and they feel pushed out and wish they never introduced you. I have had that when i brought a girlfriend of mine into my large group of close friends & then she did it to me again with a crush of mine (a while ago; and she did know he was my crush). Basically no girl code!! I'm not saying that you are doing that but she may perceive it that way. This makes even more sense if the 3 of you used to hang out & she has a little crush.

 

Sometimes I'm careful mixing friend groups because a couple of the girlfriends let's say don't have the best discretion. It's entertaining listening to their drama and they are fun people otherwise as long as we are with the mutual friends we know---but do i want them to mix with other groups of mine and almost surely bring some drama on myself, um, no!! I don't think that's the case with you but maybe that's how she perceives it or is worried about what will happen down the line or maybe she is worried about her boss being the one that will cause drama. Anyway, I can understand that it is an awkward situation.

 

Funny story, a cute guy friend of mine was visiting from Australia a while ago with his guy friends and my one boy crazy, attention seeking friend caught wind of it (she did not know them at all) the very day on their tightly scheduled trip. I couldn't meet up with them that day but she offered to meet up & show them around. I KNEW it was a mistake, knew it, knew it. She was actually REALLY pushy about it. Against my better judgement, I was like it's a free world. I'm not sure what happened but think she did something over the top slutty or throwing herself at the guys which is embarrassing. I am not romantically interested in him/them but she wouldn't have cared even if i was. That's where you just wish you had never introduced people because it affects your world.

 

Anyway, if you want to keep things as pure as possible, do not attempt to keep the social group of the 3 of you together as your new bf wants you to.. It's a different dynamic now and the ball is in her court as to how she wants to proceed and if you care about her comfort level, you will let her do that. If she had a crush on him at all, it's just like a knife in the wound. Plus if he's older, he should be able to let this go; it's of minor importance and maybe he shouldn't be partying with him employees anyway to avoid these situations. The only thing you should be worried about preserving is your separate relationship with her and your separate one with him. She could be mourning the loss of you as a single person and this group stuff but hey that's life--it evolves. Hang in there.

Edited March 22, 2018 by Versacehottie

[introverted1]

I found out something big last night: my boss thinks that my friend has a little crush on him. The two of them are very close friends. He, however, does not find her attractive.

 

So the boss is already talking about her to you -- and letting you know that he thinks she is interested but he finds her unattractive, no less -- and you wonder why she doesn't want to get involved in this mess?

 

Your friend is pretty smart, imo.

[BaileyB]

I hope I don’t have to write her off completely. She’s one of the best I’ve ever had. She swears via text that she is not angry, but she refuses to see me.

 

I found out something big last night: my boss thinks that my friend has a little crush on him. The two of them are very close friends. He, however, does not find her attractive.

 

Well, that just makes the whole situation even worse. If I was her, I would be looking for another job and/or distancing myself from the two of you too...

 

Time will tell what will happen... Perhaps, you will discover if that old saying is true... Men will come and go, but girlfriends are forever. I think you made a bad choice. But, that's just my two cents...

[act00]

Just to be clear, I would never discuss my friend with her boss. I can’t discuss him with her either, since she won’t see me.

 

And she certainly could have told me not to do it. She means quite a lot to me, and I would never have gone for that first drink with him if she told me it made her uncomfortable. It never occurred to me that she may have thought she couldn’t be honest with me one on one.

 

That said, I do understand where y’all are coming from.

 

I hope I don’t have to write her off completely. She’s one of the best I’ve ever had. She swears via text that she is not angry, but she refuses to see me.

 

I wish she had just told me the truth.

 

I found out something big last night: my boss thinks that my friend has a little crush on him. The two of them are very close friends. He, however, does not find her attractive.

 

Do you really think she was in a position to say no? I mean let's be realistic here, this is her BOSS, and she's going to tell him she doesn't want him dating you? No, she's not. And she's not going to tell you either because that is also saying "no" to her boss, because you would say to him, "Janet is uncomfortable with it, so we can't pursue this." And what else could happen? Despite her saying "no," you could very well go and do it anyway, and I highly suspect you would, and there's only so long you could keep that little secret.

 

And you are talking about her with him...and he spilled the beans he thinks she has a crush on him. This is why she wants out of this love triangle.

 

Maybe she is a little jealous and she can't be around you right now. She has no choice but to be around the boss.

 

Your intentions were good in asking her, but she was in no position to squash her boss' desire to date you.

[Keats]

All I can think, is that, your friend is really - smart.

 

She's making the right moves.

 

And seems to know exactly what is going on.

 

Yet looks like she is still getting bitten by the both of you.

 

You should let her go.

 

You don't want to be the reason why your friend lost her job or had to look for another job. She probably learnt a lesson herself too. You should move on.

Edited March 23, 2018 by Keats