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Dating is hard. I don’t think it really matters your gender, orientation, age, or where you are in life.

It sucks.

I’ve never been much of a dater. I’ve touched on this before. I’ve only had a handful of beaux in my day.

When you are a teen, and you have LOW self-esteem (Yes, I am aware that is redundant), dating is intimidating. I don’t know how a boy EVER approaches a girl (or a boy. Or a girl approaches a boy, or a girl - love is love). I’ve only ever asked out 2 men in my life and I married one of them. But the anxiety I had leading up to it? No thank you.

For the record, I’m not sure the first boy was even aware I was asking him on an actual date. But at least he said yes. And this was when I was in college.

So, my hat is off to any boy or girl, man or woman that takes that first leap and asks a person of interest out.

But at least when you are young and in school, you are meeting new people all the time. And your friends have friends to introduce you to. So it’s at least easier, and honestly less pressure, in that respect.

Because meeting people can be the hardest part of being single.

I met Dean in college. Our meet cute was doing a play together. He’s the second one I asked out – just in case that wasn’t obvious.

But it was pretty instant with him. I’m not saying I would have married him after the first date or anything, but we were practically living together after about the third date. We maintained separate addresses for a couple of years, but I think we spent every night together – my place or his – after about our third date. And even though it didn’t last the way I always thought it would, I have no regrets.

I mean, maybe I should have told him how unhappy I was much sooner. And I wish he had taken me seriously when I said I was unhappy instead of calling me a foolish teen-age girl (I was 34. And yes, I still remember. It stung.)

And obviously I regret breaking up our family, but I knew if I stayed, I would be miserable and eventually I would have made every one else miserable. I do think I made the right decision. But it was hard. And awful.

And then I was 35 and single. And most of my friends were married and didn’t know any available single men. So, I did what any other modern woman would do. I turned to

Susie sent me this as I was writing this post. I think it's a sign.

And I met a few men. Some sleazier than others. I went on a few repeat dates and one was nice enough we dated a few months.

We dated long enough to make Daniel jealous and determine he didn’t want to be just friends anymore. So eventually we became a couple. And just a month after making it official, we moved in together.

It was definitely fast. But there were circumstances…there’s no point in going into the details now.

And you know that story. I fell hard and fast and I thought it was mutual. And I didn’t worry about how fast we were moving because we had known each other for a good year and a half first so he wasn’t a stranger.

Oh. If only I knew.

And I figured we both were coming from failed marriages and we knew what we wanted this time. And we were on the same page. We had an open and honest policy.

At least I did. I thought he did too. I think he did. At least for a while. I’m not sure when it stopped. Not that it matters anymore.

And not that I would change anything. Except how it ended. Not even that it ended though obviously I would have preferred it didn’t.

People fall out of love. It sucks but it happens. And yeah, it sucks more when only one person falls out of love but that happens too. It is nice when both parties are honest about their feelings though. Even when it sucks.

But just like I can’t regret my marriage to Dean (he gave me my boys and that alone would have made it worth it), I can’t regret my marriage to Daniel.

I don’t know how to properly express all he did for me.

He loved a divorced mother with 2 boys. With a strained relationship with her ex (and that’s putting it nicely). He embraced my boys like they were his own. I had loads of debt. He gave me the courage to pursue wedding planning – and encouraged me to do whatever it took to follow my dream. He supported me when I tried to go full time and he didn’t once make me feel bad when I couldn’t do it.

That part was REALLY important.

If you have known me for a long time, like when I was married to Dean, you probably thought I was insane. Outwardly we were a perfect couple. But he did not like me spending time (or money) on anything that wasn’t about him or the boys. Including myself. Now to be fair, I did not discover wedding planning until I was with Daniel, but I do not think Dean would have supported that pursuit. He didn’t even want me to have a 401k because why would I need my own money?

Trust me that is one mistake I won’t ever repeat.

But Daniel never gave me a hard time about doing things without him. Or spending money on myself (until I spent too much). Or just pursuing my own interests that had nothing to do with him. And maybe he was faking it all along, but he treated me like I was my own person.

And I don’t know if I am saying it right but that was really important to me.

Daniel never let me feel like my identity was wrapped up in him.

And you know what else? Daniel was the first to support me when I said I could not deal with my mom anymore. He never once suggested that she was my mother and that should dismiss all transgressions or sins and I should love her anyway. That was HUGE for me this last decade. Cutting toxic people out of your life is the norm now, even if you are related to them. But it wasn’t 13 years ago.

Anyway, how can I regret a relationship that brought me so much?

But now here I am, in my forties…barely…and single again.

And once again, dating is different. But dating in your forties is a whole new level of intimidation. Especially when most of your friends are happily married with happily married friends. And you work from home.

But I did it. I put myself out there. I just wanted to get my feet wet. I was looking for a rebound. Or two.

But no. I found Rob.

And I knew he was trouble almost instantly. He was MADE of boyfriend material. He’s everything I didn’t want – at least not at that point in time.

Things are obviously progressing well. If I have any complaints, its that I don’t get to spend as much time with him as I’d like. Which is good I guess, right?

I don’t want to jump the shark or anything, but I don’t see this ending anytime soon.

And that’s both scary and reassuring. I believe him when he tells me he loves me and will never hurt me. I believe him when he says he will always be open and honest with me.

That’s why it’s scary. Because I believe him.

And I am so afraid of getting my heart broken again. I didn’t know I could hurt that bad. I don’t want to go through that again.

But I’ll risk it.

Because there is always going to be more good to make the pain worth it.

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