Difficult Conversations

Your feelings are valid and it is time to have that difficult conversation.

No Spouse. No Kids. No Respect!  Does that sound familiar?

Welcome to Day In The Life Of Happily Single. I am your Happily Single host, Brooke Bevan.  Today’s topic is having those difficult conversations with family, friends and work. Your feelings on how you are treated are valid and it is about prepping so that you can get your point across without having to walk on eggshells for the rest of your life.

I was very fortunate, I did not have to walk on eggshells with my family. My parents are really open, your life is your life, is how they put it. When I told them that I wanted to stay single and not have kids, I was super fortunate to have their support wholeheartedly. I know there are a lot of people out there who do not get that support.

Today’s whole episode is about having those difficult conversations. How to have them go the way you want them to go because people do not know unless you talk about it. The first one I want to talk about is the family. How do you have that conversation? Your Mom is excited that you are going to have grandkids, or that big wedding and you just do not want it.


That is okay, but you are going to crush maybe your Mom and Dad, or whoever is in your circle. You are going to end up crushing some of those dreams, but we are going to lessen the blow by being prepared, and being prepared saves a lot of heartache in the long run. Before you sit down and start this conversation with whoever it is if that is your Mom or your Dad, your grandparents, or whoever raised you. You need to have a goal in mind, what do you want that outcome to be?  Then we are going to work backwards from there.

Broken Dreams


You have the right to not be miserable all the time, to set your boundaries.

Keep calm and stay positive

Try to keep as much in a positive mindset as possible. I know it can be difficult. We are going to try to keep this super, super positive. The first thing you want to do is figure out how you are going to talk about it. This is going to be a lot of ‘I feel’ moments, I see myself, I, I; you are going to see a lot of that in this conversation.

Map out how you want this conversation to go. Once you have those talking points, feel free to practice. It does make it easier when you come off with confidence. Nervousness is okay, but being confident about who you are is going to be the selling point to whoever you are speaking to.

You are also going to want to set the time and place. It sets the importance of the conversation that you are about to have and sets a time limit. I am going to talk to this person for 30 minutes at max. That way it gives you a timeframe to work in, because some conversations can take a long time, and then you end up talking yourself into a circle.

If you give yourself a time limit, then you are not going to talk yourself into that circle by accident and set ground rules. When you sit down with this person in the place, time, that you want to do it, ask them. Remember, watch your language because we are trying to get people on board, and not push them away.


Language is really powerful here. Just be very mature, and say, “I need to have a very serious conversation with you and I am going to need you to let me talk.  In the end, I am going to give you an opportunity to talk, but you need to not interrupt me, please.” If the person you are talking to respects and loves you, they are going to give you that. If they do not respect and love you, this conversation is going to be a lot harder to have just because they are not going to give you the opportunity to talk.

That is really difficult when you have that person who does not respect you, or see you, or give you that time and space that you need. That is a whole different conversation. Do you really need this person in your daily life? I know that can be really hard, especially with a family member.

You have the right to not be miserable all the time, to set your boundaries, and for them to follow that.  If they cannot follow, that is really on them.  You need to put your health ahead of their rudeness, is the word I am going to use.  We are going to set some ground rules. Let me talk, please do not interrupt, let me go through this.  Then you are going to really watch your language. Again, we are trying to convince somebody, who has a different idea than us, to be on board, what is best for us. 

You say, “Hey Mom, I have made the decision in my life. I do not want to get married. I do not want to have kids. I am planning my life around staying single. I know that you were looking forward to having grandkids, and me getting married, but that is not what I want out of my life.”  Have a goal of where you want your life to go. That really helps too. This is what I want out of my life, and this is what I am doing to achieve it.

Now you have given them something else to think about because now it shows that you have planned your life in a certain way that did not include being married or having kids.  When you are done talking, give them an opportunity to talk as well. You need to stay silent, not interrupt them as well.

Let them have their moment. They have given you that moment. Now give them their moment, and you just want to listen to their concerns. Some of the concerns are that I am scared that you are going to be lonely. I am scared that you are not going to have anyone to take care of you. I am scared that something bad is going to happen and have pre answers for these in your head already.

You have already thought out the objections to your wanting to stay single and not have kids. It allows you to let them speak and then allows you to respond.  You are worried that I am going to be lonely. That is okay. I have a really good group of friends. They support me. We do activities together. I am part of these clubs that I am getting my social interactions through. I am planning my finances in such a way, as I age that I am taking care of. I will be here and here, so you do not have to worry about me being alone.  That is just a way to alleviate their fears. There might be some anger from that person that you are speaking to.

I am talking parents here, because maybe they were hoping for grandchildren, and you do not want to have kids. That is a really difficult conversation on its own, just because our society wants us to procreate and for some parents, the label of ‘grandparent’ is very important. If you are lucky you get siblings who have traditional views. They get married, they have kids, your parents will be fine.

But, if you are the only one, that is you are an only child and they are expecting grandkids, that can be a really devastating thing for a person who wants to be a grandparent. You have to be really respectful of that feeling, even though you say, “This is my life. I am going to do what I want.” Those feelings go very deep in people who want grandkids. So be very respectful and listen to them, but stand your ground, and just keep having that dialogue.

This Is My Life

At some point, they will come around and accept that this is not going to be part of your life. What if they say something to you that angers or upsets you? This is a really hard one. We are all emotional beings, but sometimes we have to detach just a tiny bit. Take a step back from what you just heard, and actually analyze it.

Are they saying it to be mean? Are they saying it out of anger, or are they just upset about the situation? You are going to use that ‘I’ statement a lot, ‘I feel’, ‘I think’, and you are going to own that moment. I understand that you are really upset about this, or this upsets you, but I feel that this is best for me.

Sometimes it is just, it is not going to happen. The cross-communication is just not working. A good one to say is I am having a hard time understanding it from your viewpoint, but I do need you to respect my choice. It is difficult, especially if you are not someone who likes confrontation. It can be very difficult.

I am fortunate that I can have difficult conversations because I am one of those, let’s just rip the band-aid off for people. Honestly, I would rather get it over with and deal with it than let it stew.  Do not let it stew, because that is taking time and energy from your life, putting it somewhere, that is negative, weighing on your body. Wrap it up. You gave yourself a 30-minute time limit, wrap it up and move on.

It might take some time for the situation to digest on the other side. Give them that, but remember to set your boundaries, and stick to them, because boundaries are really healthy to have.  If the other person is not going to respect those boundaries whatsoever, then that is a relationship you really need to think about.

That is why it makes it a difficult conversation. The other side of having a difficult conversation, especially with family, is talking about moving out of your house into a retirement home or having to move somebody who is single, that you love, into a retirement home.

You are going to have to be really super respectful about that. Again, watch your language. It is that person’s life, and it can be really difficult to know that you have the best interests at heart, but it is their choice. You have to respect that choice, even if you think it is wrong because they are probably thinking you are wrong.

Don't fight Talk

It is all about respecting each other. You want them to move into a home for retirement, you are going to have to see what their objections are, and then find counters to those objections in a respectful enough way that you are not getting them to fight you. Being open and being very watchful, your language and how you are speaking to them. The tone is really important. Sometimes we can be tone-deaf, where we are trying to get our purpose across, but we do not know how the other person is actually perceiving us. 

Just keep having those conversations, and maybe chip it away a little by little, but that is a really good conversation to have fairly early, especially for moving people out of their homes. Have that conversation early, and have a plan in place, because plans take all the stress off things that happen later.

The next one we are going to go to is having those difficult conversations with friends. For the most part, I am hoping you are comfortable with your friends saying, “Hey, time out. Can you stop trying to set me up on dates? I am very happily single. This is the life I want to live.” It is almost identical to having that conversation with your family because your friends are kind of your family if you think about it.


These are your chosen people. These are the people that you brought into your life to better yourself. If they are not respecting your boundaries, this is something you think. Is this person actually a good friend? Do I really need them in my life? When you set boundaries, you will lose friends.

Your real friends will accept the boundary and be happy for you. A fake friend will get really upset with you, and you will have to make a decision if you want to keep them in your life, or not. When you start having true friends, these conversations become really easy, because there are really no barriers between you. That is just really nice.

The hardest one, we are going to talk about here, is the work conversation. I wish I had actually done this in a respectful manner when I was an employee. If you have listened to my previous episodes, I was a horrible employee. I will put that out there, I really was! Thinking back on it, now, these are things I should have done.

Especially at work, when I had worked with partners who were married with kids.  I was single. There was a lot of stress to be a team player, and pick up a lot of the slack. When you are doing it all the time, it gets to be too much. Having this difficult conversation with your coworker, your boss, your supervisor, whoever it is, is the toughest one because it is work.

The first thing you have to think about it, you actually have to plan the conversation just like we did for the family and friends. You have to plan out what you want to say. You have to have your main talking points. You have to think about what the objections are, and how to counter them. You need to be really direct, and very specific. When you are not specific, it just sounds like you are whining. That is the worst part, is that you have genuine feelings, but they see you as whining.  

Be very direct and very specific. “When so-and-so does not show up for work, because of a situation with her family, I am asked to pick up the slack like on Friday. When so-and-so’s kid was sick, I had to do not only my job; which was this, this and this, but I had to do their job as well; which was this, this, this, this, and I could not do both.  I did not have enough time. Then you were upset with me because I did not have enough time. But, here is a solution I think would better suit, is to have somebody, who is on call, to come in and fill in for that person, or I do not do their work, I just do my work. Then they can do their work when they come in. But you need to have a solution. You know what I mean?” 

If you have a problem, you need to have a solution to work with, or you do not get taken seriously. Comes off as whining in the workplace. You have to watch your language. I know some days that can be hard. I get it, I totally get it. But you are trying to get this person on board with your ideas.

You have to work with them in a  positive non-confrontational language. It is not “You have to do this, but I am feeling this. This is my situation. I need help.” You need to make it non-confrontational and not blaming. The blame is a really hard one, because, “It is not my fault you keep piling me with extra work when my coworker does not show up. Please stop!” 

You cannot be confrontational. It just gets everybody fighting it and nothing gets situated. Then you get seen as a troublemaker. It is horrible, but it works. The next hardest one is because we are emotional beings. Managing your emotions. For a lot of people, this is really hard, but you need to step back and look at it from a logical point of view.

What is going to win you this argument is the logic, not the emotions because a lot of bosses out there do not give a shit about your feelings. If you can break it down in a logical manner for them, and make it so it makes sense, it is hard to say no to. I hate this word, it is being empathetic. No one is being empathetic for your situation, but you are expected to be empathetic for others.

Work Overload

If you have to play the card, it is, “Oh, I understand that their kids need them, blah, blah, blah.” Whatever it is, fake it until you make it, because honestly, especially when kids are involved, if you are negative towards kids, you are the bad guy at any workplace. So, ‘fake it until you make it’ kind of thing.

Say what you need to say and try to be even fake empathetic. Even if you are in your head going, “I fucking hate kids. Why do I have to deal with the shit, when you are having issues with your kids, or your spouse? Why do I have to deal with your crap?” Even if you are saying that in your head, don’t say it out loud.

There are a lot of things I say in my head that I do not say out loud, but I really, really want to. It is all strategic. Then at the end allow for questions, be ready,  prep your answers a little bit. 

Expect some pushback, especially in the questions. Stop. Do not automatically respond to the question. Stop, and actually think about it. They said this. How am I going to counter it? So that they have to see it from my point of view. Take your time in the conversation, ask for it as a legit meeting. Just do not knock on your boss’s door and say, “Hey, we need to chat.”

I want to sit down and have a meeting with you. Can we do that? Do it in the most professional way you can, because the more professional you are, the harder it is for them to blame you for things. Especially, in a situation, where family and kids are involved.

Difficult conversations, are difficult, no matter which way you look at them. You have to think, would you rather just rip the band-aid off, and deal with it and move on. Just have that relief that it has been dealt with. Or, if you put it off too long, are you making yourself worried and sick, anxious and just miserable for a longer period of time?

Why would you do that to yourself? It takes a little bit of courage. Courage does not mean that you are not scared to do it, or nervous to do it. It means that even though you are scared or nervous, you are doing it anyway. You are going to find that when you find that little bit of courage to stand up for yourself and to have those difficult conversations and say, “These are my boundaries.”

You are going to feel better. Stick to your boundaries, people. Stick to your boundaries! You are going to feel better. That is taking control of your life. That is the best we can do. You are going to find people who do not respect your boundaries. They are everywhere, and they do not care about you, but you need to care about yourself.

Have those difficult conversations. Watch your language. Be positive. Take control of your life. 

I will see you guys in the next episode of Day In The Life Of Happily Single!


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