Dating with Children: Hope & Expectations

Dating is hard.  Dating with young children is harder.  Dating with older children in nerve wracking.  My son is 16 and now has opinions about who I date.  He wants me to be happy and is very protective of my heart.  He has seen it get broken and so he wants to make sure I date someone decent and kind, who treats us both well.

My son does not meet the men I date until it is something serious.  I have always felt a man needs to earn the pleasure of knowing my child, and few have qualified as being good enough.  Unless I am in a relationship with a man, he does not meet him, and that has been my rule.

“Daniel” has complicated that rule a little bit.  We spend a lot of time together, talk daily, and have begun to intertwine our lives.  I have sent my clients to his business and he has become my sounding board in terms of not only work, but a man’s perspective on things I deal with as a mother.

I was recently faced with a work opportunity that had me panicked for a minute and he was my first call.  He is smart and wise, with a brilliant mind for business and unnerving clarity about who I am as a human being.  We have different worldviews, but he is helping to redefine mine.

We have not known each other long but our connection is undeniable.  It is also unexpected which makes it scary.  I have been looking for someone for a long time and when that person might actually be real, it knocks you on your ass.  I have now officially been knocked on my ass.

Daniel and I are dating. We have not had any discussions about being exclusive, or removing our profiles from JDate.  We are simply having a good time together, getting to know each other, and enjoying the company of one another.  It’s all very grown up and civilized, which feels good.

Sidebar:  The truth is I want him to be my boyfriend, I want us off of JDate, and I want to think of him as mine.  I would never say that of course because I am cool and playing the dating game.  That said, I suck at the dating game as you all know, so I’m more pathetic than cool.

I’m not sure if I want him to be my boyfriend because I’m there with him, or because it will make me feel better about having introduced my son to a boyfriend over a man I am simply dating.  I suppose that is the real struggle when dating with children.  It’s quite complicated.

Making it worse is the fact that I write a blog about my life.  He will read this and either think I am passive aggressively asking him to be my boyfriend, overstepping boundaries in terms of his family, or simply a brave and lovely girl who likes him. Dating sucks.

Daniel called me on Friday to say that he’d like me to meet his kids.  His oldest daughter is in town for a visit from university, so it was very sweet that he wanted to share his limited time with her.  It was nice, and that he wanted me to meet them this early was quite surprising.

Daniel is not like anyone I have ever dated.  I am thinking outside the box on this one and so rather than think about it too much and talk myself out of it, I agreed to dinner and we planned for me and my son to meet up with him and the girls.  Everyone would like each other, and it would be fine.

Meeting kids, particularly when they are older, is really hard.  They are old enough to form opinions about you, and you of them.  Everyone loves a little kid because you can teach them to like you, but with an older child, you are on your own.  They like you or they don’t, and if not, it’s over.

If my son met someone I dated and told me he did not like him, I would be done.  That’s just how I role.  Because of that feeling, I felt sick all day Saturday.  My stomach was upset and I felt nervous.  I was certain everyone would love my kid, but would they like me too?

They are daughters, close with their dad, and I’m sure protective of their mother as my son is of me.  I wanted them to like me because I like their dad so much, and while I know I am fabulous, I was worried all day.  I changed my outfit 5 times.  I was absolutely ridiculous.

At dinner I was greeted with a hug by both girls and it took all my strength to not cry.  I cry at everything, but this was special.  I really like these girls.  They are interesting human beings and seeing young people develop their own worldviews is fascinating to me.

The older daughter is very open.  She thinks about things, has a generous spirit, and an inquisitive mind.  She is finding her way and to hear her talk about her future is exciting.  She is the type of person I gravitate to because she can teach me things.  Her future is very bright.

The younger one is an observer and I found myself wanting to get up during dinner to hug her.  She sits back and takes everything in.  She looks at her sister with adoring eyes, and tolerates her father’s jokes with a smile that is heartfelt.  The are both artistic, kind, warm, and very pretty.

To sit with Daniel and watch our kids talking and laughing made me happy. You can tell a lot about someone by how they are with their children and from that perspective, this is a wonderful man.  Seeing him with my son makes my heart flutter.  Daniel is good, and I have a crush on him.

We had a lovely time together.  It was comfortable and safe, so in the end my nervousness was unfounded.  There was never any need to stress out about dinner.  We both have mature and wonderful children, we are grown ups, and this was a natural step in dating at our ages.

I’m not one to plan out the future, but I am a dreamer.  I dream about how I will spend my lottery winnings.  I dream about the next stage of my career. I dream about dancing at my son’s wedding.  I dream about a world where there is no hate.  I don’t plan for these things, just dream about them.

My relationship with Daniel will now be something I dream about.  I am invested in a new way.  Our families have connected and so it changes how we date.  There is a level of intimacy that comes with involving children into your dating life that I was not sure I wanted, but I welcome.

I do not live my life with expectations.  I do however live my life with hope. I hope things continue with Daniel, and to be honest, I do have some expectations.  I expect his choice in taking this step was genuine and he will protect my heart now that we have taken this leap.

There are no guarantees in life, but there is hope, and that feels good.  Love is possible today.  Not only for me, but for all of you who are searching for it.  I have hope for us all.  I am happy. I am nervous.  I am skeptical.  I am hopeful. I am keeping the faith.