The Anguish of Dating as a Single Mom

It took my therapist several times to tell my about step families before it sunk in. She said even if you find a man, fall in love with him and become a family, it will always be you and your son: a relationship that he can’t join and you and him: a relationship your son can’t join. Of course we would be able to form me, him, and my son as a separate relationship with it’s own culture but it won’t ever be the primary dynamic of the household. and no one is ever going to be able to come in and become the parent for my child. That responsibility is mine to carry alone. The more I date the more I see this. Sir is an outsider to my son and I’s bond. My son is the outsider to Sir and I’s bond. Only rarely do we all bond as one unit.

My son and I have been a 2-person family since the day he was born. I have decided the culture of our family and home. Together we have developed the rhythms, methods, and tone of our family. When my son was younger and I would seriously date a guy, it was a bit easier, but even at a young age, my son showed signs of possessiveness, jealousy, and being intimidated by someone new seeking Mommy’s affection and attention.  Over the years all the men have had opinions about how I parent, especially in regards to bedtime since that affected them the most.

I breastfed my son for the first two years. I was really into attachment parenting so we co-slept. It was easier anyways; if he woke up in the middle of the night hungry, all I had to do was roll over, stick it in his mouth, and go back to sleep. When he was a toddler, I would lay with him for nearly an hour every night to get him to sleep. He was so in sync with me that even if he seemed sound asleep, no matter how quietly I rolled off the bed, many times he would awake instantly if I tried to leave the room. By the time he was ready to go to school I had tried every trick in the book besides the cry it out method. I wanted him to form a secure attachment style from knowing he would have his every need met, yet despite my efforts he still ended up with an adjustment disorder by the time he was in preschool.

My son is almost 8 now and the only purpose his bed has is something to jump on while he watches tv. He either sleeps on the couch or in my bed and he always wants me in the room with him while he falls asleep. This works fine for me mostly, even when Sir is over we both go on our phones until he falls asleep then creep to my room. But lately he has been taking longer to fall asleep and it makes me a little aggravated. Saturday night Sir was there and I got even more upset with my son’s inability to fall asleep. I really wanted to talk to Sir and his time was limited.

I told my son we would be in my room and left him on the couch.  He started wailing about how afraid he was, crying, and breathing like he was going to have a panic attack. I looked at Sir and he smiled. He said that my son just wants to get attention and it works with me, that’s why he is like this. This is so frustrating for me to hear. I love Sir and respect him but when it comes to parenting I reserve the right to be in charge. I have heard this trope countless times from too many people.  In fact, I don’t complain about my parenting griefs to anyone but therapists anymore, because I am so sick of mainstream parenting and discipline advice. It doesn’t work with my son. He has oppositional defiant disorder: my living hell.

Of course there is the argument that my lack of boundaries is what caused him to have this disorder.  Which would make Sir right. There is also the argument that kids who have it just don’t respond to traditional methods and it isn’t the parent’s fault. My therapist says it’s a circular argument like the chicken and the egg. Were the parents lacking consistency and strong discipline first or was the child oppositional first? Regardless, of the answer most people have no idea what kind of child I am up against when they judge my parenting choices. Sir has seen my dynamic with my son more than most, but he still doesn’t get it.

Sir said my son will still be doing this at 16 if I keep letting him. He said this is how kids end up living in their mom’s basement when they are adults. So I stayed in the room talking to Sir and ignored my son’s cries and pleas. We did get to talk and Sir went out and consoled my son some which was nice, but in the end my son won. Sir left and he went to my bed while I watched tv in the living room.

Even the strongest willed, most dominant personalities are no match for an ODD child. I have learned that getting in a power struggle with him is pointless. it’s actually giving him what he wants: an opportunity to be defiant.

Last night, I got a message from Sir, saying, “You may have visitors”. When I asked him what he meant he said that was for him to know and me to find out. I had no idea what he had up his sleeve but I had been trying to get my son back on his routine and had made sure he had gotten exercise. So, at bedtime I sent him to my bed with a book, teddy, and kisses. Shortly after Sir showed up with one of his friends, an old friend of mine I hadn’t seen in years. We visited a few minutes and then he left Sir with me. I soon found out that Sir was going to spend the night! I was so excited. Unfortunately, my son was already falling asleep in my bed. After all the years of dating, I still haven’t come up with a good method for having boyfriends over night.

As much as I want Sir to be my life partner and for us to continue to grow as a couple, I am also very much afraid. Being a single mom, I have been forced to be in charge, make all the decisions, and make things work. It toughened me. It made me stubbornly independent. No boyfriend ever stuck around for long. As lonely as it is being single, I have gotten used to it. Having a boyfriend spending time in my home, however, is awkward. There was the guy I dated for a few months who wanted to see me every night. I didn’t know how to tell him I wanted to be alone without upsetting him. And when I wanted him to leave, there was no nice way to say that either. My present other boyfriend (BF #2) and I started off at a hot and heavy pace and he would spend quite a bit of time in my home. At first I loved it, he was my addiction. It felt like I just wanted him to stay and never leave, but I am sure if we hadn’t started fighting all the time, it would have worn off anyways.

Sir got to my house at 8 pm. I was watching the Bachelor. I asked him what he wanted to watch and he wanted to watch a car show. I was just happy to lay in his arms, be caressed and squeezed by him, and tell him about my day. Though in the back of my mind I wondered if we would always watch what he wanted. We had sex on the floor. During foreplay, my son popped out of my room to use the bathroom. Luckily I don’t think he saw us. Foreplay for us is very focused on power dynamic which is not something I want my son to see. We paused foreplay until I was sure he was asleep again.

After we fucked, I took my meds and Sir offered to go lay down with me. I wasn’t going to fall asleep for awhile and I knew he stayed up much later than I, so I told him I would tell him when I was sleepy. These working out the details of how we can coexist together comfortably for one evening is, again, awkward. It is definitely not like a fairy tale or a romantic comedy anymore. If it ever was. He finally sent me to bed, but we had to move my son to his room. Sir said he would join me later. I was a little relieved, because I still get anxious sleeping with someone besides my son and I had to get up early to go to the gym in the morning.

Before I went to bed, Sir said if the point comes where we are living together my son sleeping with me is going to have to stop. I nodded my head and agreed, but inside I wondered how I was going to make that happen. I comforted myself with the thought that Sir wants to live alone for another year before we even consider that. Maybe my son will grow out of it by then. Despite what Sir says, the professionals assure me he won’t still be sleeping with me when he is a teen.

It was so nice waking up next to Sir this morning and cuddling him before I got up to make coffee. Before I left I asked Sir how he slept and he said I still snore really loud, but he survived the night. Sigh. I guess I can’t blame that on my son or single parenting. I got to give him kisses though, before I left the house. That made all the awkwardness worth it. And Sir said he won’t break up with me just because I snore.


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