Relationship trust and tension. Are my boundaries reasonable?

[Carlo500]

I am 50/male/fit/professional. Girlfriend is 42 fit/entertainer. We both are attractive and have jealousy and insecurity issues. One issue that is tearing at us concerns her "boss" and close friend that she has known for two decades.

Background on her: she worked as a bartender in a strip club, but it was a deal breaker for me. She quit, saying our relationship was more important. She also has a social media following, and would post swimsuit pics and other sexy pics. I was uncomfortable and she stopped posting it since.

My gf is generally open and shared that her boss and close friend expressed his love for her eight years ago. He has what is supposedly an open marriage, but in reality it is an unspoken, unclear arrangement. He has slept with two other women in their working group, one of whom is married and not in an open situation. His wife does not know and it would create a mess if truly out in the open. My gf is far more attractive then him and these other women. She insists she rejected him and it caused tension. They worked to re-establish a working relationship over time. She insists that it is professional. She also provides access to her phone and puts him on speaker when he calls. I found a two year old conversation where he was pushing to work with her on a project. She eventually agreed, then SHE joked "bring a dildo." She has a crude sense of humor and has toned it down at my request. A couple weeks ago he stated he missed her but when laying in bed thinks of her as a blowup doll. On another occasion, he made a joke about the work semen. Needless to say, I find this unacceptable. I wanted to confront him. I wanted her to end this work relationship and friendship. This upset my gf as I can be controlling. She insisted that she talk to him that there be no more sexual jokes and that I simply trust her.

What is the right course of action? I want her to fade this relationship (she needs the work) and never do a private work session with him. She says that is too controlling and I should trust her to set boundaries.

[Rose Mosse]

If she disagrees with you, you cannot force someone to do something. Don't keep forcing someone to do your biding. This is the definition of controlling. You're trying to bend someone to your will.

It doesn't appear that you both share the same sense of humour or that you respect her humour in relation to her work. My husband works in an industry that some would call very crude and the way that they speak to each other is harsh and full of obscenities, dirty humour and probably includes a lot of racist, homophobic and extremely derogatory comments. If you haven't been dating for more than two years at least, you're not going to understand each others' humour. Hers seems to be tied to her work to relieve the day to day objectification and dehumanization of people at a strip club. Put the pieces together and do the math, whether you can accept her the way she is.

If you are interested in her as a person, you'll have to accept her as she is and be willing to accept her friendships and her humour. You may also be at a crossroads where you're finding that her personality is so indelibly changed by her work and she continues to be influenced by the same crowd that your differences are irreconcilable because you cannot accept her personality or the other influences in her life. I don't think her friendship with her previous boss is appropriate but that realization should come from her.

She's changed a lot for you or for the relationship. I would be very wary of resentment building. If you are continuing to impose rules and changes on her, you are creating your own perfect storm.

Be honest with yourself. I have a feeling you might have fallen in love with her for her looks without getting to know her too well or being too familiar with her as a person. Take a step back if this isn't working out for you.

[Leah33]

I think your boundaries are reasonable but this doesn’t sound like a typical nine to five job.
What type of “entertainer” is she? Because I’m guessing she’s not a balloon twister or mime.

[pippy longstocking]

she worked as a bartender in a strip club, but it was a deal breaker for me. She quit, saying our relationship was more important

She also has a social media following, and would post swimsuit pics and other sexy pics. I was uncomfortable and she stopped posting it since

She also provides access to her phone and puts him on speaker when he calls

I wanted her to end this work relationship and friendship. This upset my gf as I can be controlling.

I want her to fade this relationship

I found a two year old conversation

^^ All of that is absolute control and it rang so many bells with me it is like the opening of Big Ben in my living room .......I am not shooting you down because of my bad experiences but I know it will not end there , there will always be something else , then something else , on and on .

However

She isn't exactly making it an easy run for any man , she needs someone on the same page as her ..she needs someone who just accepts who she is , how she talks , what she does and can sleep at night knowing they trust her ...............that my friend will never be you .

I believe, I am sorry to say that this is like pouring oil on water . it will never work . Best wishes with it all , because it isn't good for either of you .

[Wiseman2]

How did you meet? How long have you been dating? Stop trying to fix, change or control her. What you see is what you get. If you feel she is not right for you simply move on. Why are you going through her phone, telling her to quit her job or making her put calls on speaker? If you can't handle dating strippers, entertainers etc date other types of women. Get a grip on the jealousy and possessiveness.

Girlfriend is 42 fit/entertainer. she worked as a bartender in a strip club, but it was a deal breaker for me.

[melancholy123]

How did you meet? How long have you been dating? Stop trying to fix, change or control her. What you see is what you get. If you feel she is not right for you simply move on. Why are you going through her phone, telling her to quit her job or making her put calls on speaker? If you can't handle dating strippers, entertainers etc date other types of women. Get a grip on the jealousy and possessiveness.

Exactly what I was going to say. You are a control freak.

[DancingFool]

Your boundaries are reasonable, your behavior and dating this woman in particular is anything but reasonable.

What on earth are you doing here? Make her change this, quit that, do that. For the love of, you do not treat anyone like that. If you date a woman and lifestyle/values/humor/language/behavior do not match up with yours, you simply part ways. You do NOT control, manage, demand change, etc, etc, etc. What a crazy toxic mess you are creating. Not to mention she is completely right to tell you no. She'd be even better off dumping you instead of making so many concessions.

Find a woman to date whose life you don't need to change. Since you are so hot and fit, that shouldn't be a problem.

[bluecastle]

While I understand the source of your nerves, you do sound quite controlling. I couldn't help but get the impression that control is a big part of your connection—control and insecurity, with you trying to temper your insecurities by controlling her. She, meanwhile, submits to that control here and there—her insecurities. Hard, in short, to build a secure relationship when the chief currency is insecurity, when heat is generated through jitters and disrespect.

I assume you didn't have a problem with her social media feed before you started dating her, and I assume you knew how she earned a living. Asking someone to change those things once they commit is a pretty big overstep, since the message is that you don't accept her for who she is, which is all anyone wants. If you want to put it in the context of boundaries, which are personal, it's a bit like this: you broke your own boundaries in getting serious with someone you can't respect or be secure with, then asked her to accommodate that self-deception by making drastic changes to her life and personhood (her boundaries) so you'd feel better—along with allowing you to monitor her phone and eavesdrop on conversations to be further soothed.

None of that works. It's possession, not affection. Control, not trust. And it probably puts both of you in an edgy place where neither of you much like who you are, alongside each other, rather than feeling accepted and cherished, as neither of you are behaving in respectful ways. Sounds like now she's starting to resist, which is inevitable, because no human being likes to be controlled. Humans are autonomous creatures. Pin them down and they'll push back, eventually, and the harder they're pushed the less graceful the means with which they'll push back.

Thing is, she is right: she gets to set whatever boundaries she wants, and your job is to trust her, and trust yourself to assess if those boundaries work for you. And vise versa. That's communication, connection, a dance in which two people build a world that respects both their individual natures and their connection. I get how her lifestyle, who she associates with, and how she associates with them is challenging—wouldn't be my cup of tea, though I'd have known that from a quick IG scroll. That's me, you're you, she's she. She needs someone for whom all that is a fine cup of tea, and the most caring step right now might be admitting that you can't handle this.

I wish I had better news. You dig her, she digs you. But she needs to earn a living and feel good in her skin, and if her choices on those fronts don't make you feel good in your own skin—well, that's what is called incompatibility.

[Honeycomb8]

Just break up. She sounds shifty and you don't trust her.
Why bother.

Find a woman in a professional field that doesn't joke about dildos with sleazy bosses.

[maew]

What is the right course of action? I want her to fade this relationship (she needs the work) and never do a private work session with him. She says that is too controlling and I should trust her to set boundaries.

She's right... she has literally bent over backwards to appease you so far... but everyone has their limits.

You knew who she was when you started dating her, why do you want to change her? This isn't Pretty Woman... and Pretty Woman isn't real life.