Bf (30M) has a difficult time setting boundaries and saying ‘no’ to people

TL;DR and questions at the end

Its escalated to the point where I (23F) have been the one having to do a lot of the talking and saying ‘no.’

I can understand he doesn’t want me to burn any bridges and stay friendly with people. Although I’ve warned him about the wrong people getting too close. I’ve also told him you can set boundaries and confront people and still remain friendly and calm.

For instance, we have this neighbor who kinda reminds me of his mom. She came over once to talk about our shared easement road construction we are all collectively paying for. Ever since I met her I knew she was a bit manipative, I can totally tell my bf acts somewhat like he does around his mom around her, almost protective and submissive at the same time. I think this is totally okay and I think its great he might want to be friends with her but I’m not okay with him just submitting to any of her demands because shes tapping into his childlike psyche from when he was little with his mom to manipulate him.

Our first conversation she was eyeing me down like crazy, and every conversation since pretty much goes with her trying to get us to do stuff for her, making demands, telling us what to do with our house and talking about herself likes shes a saint and bashing other people around her, almost likes shes venting to us. She barely asks about us or who we are.

A few days ago she and my bf were outside talking and she was making all sorts of demands from him to call this person and do that. I could stand to hear her talk to him, a very intelligent doctorate, like a child anymore about how to do construction on a road with her lack of know how on the subject.

I came outside to kinda monitor the conversation and clarify what my bf was afraid to and make it clear and ask if she was in fact making sure the payments were split evenly and to remind her to just leave the construction up to the road experts we hire. She originally wanted $35,000 for a $5,000 job for this easement road; the payment would be split four ways between the houses. My bf stands there just listening, I was still friendly but told her $35,000 is really a lot to ask for and we should search for other option, she made excuses like ‘I need this road done now.’ Since this conversation I typically do a lot of the talking with this neighbor and my bf just sits there. I’d rather have her feel like she has to talk to me and she can’t sit there and manipulate or pressure my bf like she wants.

We also have a bigger issue with the old neighbors son. He’s basically dealing drugs behind our property and trespassing. My bf has let it go on so long (about two weeks) although I’ve asked him to take action. He keeps saying he’ll talk to the guy. He wants to make sure its day light so he doesn’t pull a gun on him. I totally get that although I also feel this has gone on so long and because we haven’t confronted him its not helping any.

I feel if we both confront the neighbors son in the day time about not being allow to cross the property it might help, we can record the conversation. I’m almost just so tempted to just talk to the guy myself but I also feel thats not my place as my bf is the owner of the house. The police in our area basically say its our problem because they think its a shared easement even though he is trespassing on our property only granted to us and the state water company. What my bf didn’t tell the police or me is that its contract that the our property the neighbors son is crossing is in fact not permitted to anybody but us, but he just lets it go; its so frustrating idk why he doesn’t just clarify to law enforcement that he is indeed not allowed on the easement property and its on contract.

Part of me thinks a lot of this hesitancy surrounding saying ‘no’ and setting boundaries with people has to do with his mother. About two months ago his mom came to stay and wanted to stay for a whole month. I thought the month long visit was a bit much but I also thought it made since she wanted to spend time with her son and she came a long way. So long story short she had absolutely no respect for our household or our boundaries at all. I will be honest, some may disagree with this concept and thats fine because we have reasoning for it. I am still a gf, because we moved in together relatively quickly after dating only a few months and it was just financially the right move for both of us to save money and move in together. We were both very serious about each other, have talked about marriage someday and are slowly getting to know each other more and more each day. In fact, this issue I have with him saying ‘no’ and being hesitant to set boundaries with others is really the only issue we have.

The mom walked around and demanded things like she owned the place. Demanded we drop 10K on a car just for her stay that she didn’t even use, etc. After all the bs she caused over her visit I told my bf to stand up to her, he wouldn’t and made excuses for her, I told him I’m leaving while she is here because he as head of household or the man of the house is allowing such boundaries to be crossed and I didn’t know if I wanted to stay in this relationship.

He finally broke down and made me have a sit down discussion with her, he didn’t defend me at all, just sat there neutral. The mom said sorry and things were okay for a few days, then she started up again, I was the one that had to tell her no and then she went after my bf, her son, and when he said she couldn’t come over when ever she wanted like she demanded, she lost it and said the relationship was over and we haven’t heard from her in two months.

Confronting the mom and having to discuss boundaries with her was not something I really wanted to have to do, I wanted nothing but to get along and respect her although really had to be done. Plus, I have a hard time respecting anybody that act like as much of a child as she was during her visit. Of course I was civil and polite and can obtain basic human respect for her but to say she has earned my respect in the sense that I look up to her would be a lie.

I also know I’m not a wife yet and she certainly doesn’t see me as such because we are not married and I know that but I had to stand my ground and let her know she was crossing the line because my bf would do it was necessary to me. If we where to get married it certainly was not in my best interest to start off on the wrong foot and have her think its okay to cross boundaries and feel comfortable doing so.

My bf says he agrees with me but has gone back and forth on it. This ‘trial period’ is also why I am a big fan of moving in and getting to know each other completely before tying the knot. I don’t intend to stay too long without a proposal or just move in with anybody by any means although I do see value in making sure your happy and content before you commit for life. I really am not a fan of divorce or marrying the wrong person either as I have seen divorce and family disfunction destroy so many families.

I also come from a narcissistic family and would even label myself as the black sheep or scapegoat. I do somewhat understand what its like to go through living in a toxic family dynamic even if it seems normal on the outside or if my bf and I come from two different positions in a separate family dynamic.

My bf is a lot more goody two shoes, innocent, but I respect him and really look up to the fact that he really does try to do the right thing at the end of the day. I am a bit more of a rebel, or lone wolf even (cringe to say this I know), although its been a long lonely road and all I can say is that I am very pleased with who I have become on my own and only allow people close that reflect good in my eyes.

My bf and I have talked about these issues somewhat and we do think that I sometimes over react and he under reacts. He is always hesitant to pull the trigger and sometimes I wanna pull too soon.

I also think my intuition is a lot sharper than my bf’s. Sometimes he’ll be around people and think nothing is wrong when there is. I tell him what happens and he just simply blows me off until it blows up into a problem and I have to ‘nag’ him to handle it.

I feel I really should be the one to say ‘no’ for him, but he should be the one to do it. Although when I don’t do it nothing happens. I’m afraid I am enabling him to avoid having to confront or stand up for himself or us.

How should I handle this issue?

Should I sit back and wait for things to get bad for both of us before I do something?

Is it a red flag that he has a difficult time setting boundaries and saying ‘no’ to certain people?

Is it really right or my place to feel like I have to ‘nag’ to not just get what I want but what I deserve and expect to feel safe and cared for in a comfortable home?

Is there a way he can change and get better with this issue on his own?

TL;DR; My bf has trouble saying ‘no’ to people and its effected the relationship. He has a difficult times saying no to the neighbors demands with getting our shared easement road, to the neighbors son trespassing on our property and to his own mom. I feel it shouldn’t be my place to have to push or ‘nag’ him to take action with certain things and confront issues with people. I also don’t feel I should always have to be the one to say ‘no’ for him on our behalf just because it’s difficult. I don’t think its right for me to step in and say ‘no’ to him but sometimes I really feel like I have to do it so we don’t get walked all over as a couple because he will not step in.