I used to not have a problem putting myself out there,” my friend Randi said. “I’d go out, date guys, no problem. But then I got in to the more geeky side of things and when I’d flirt with guys they’d get this deer in the headlights look and I’d get self-conscious and now it’s been a while since I’ve been out on a date. I guess I’ve just forgotten how to flirt.

I’ve had conversations like this with many of my friends in their forties and fifties. They used to date, they want to date, but somehow they just stopped dating. And they aren’t sure why or if they are really ready to do something about it.

“Where do you ideally see yourself in 10 years?” I recently asked my friend Dave. “Do you picture yourself with someone? Or do you see yourself alone? What would make you happy?”

It depends,” he confessed. “Some days I see it one way, other times I see it the other.

I’ve never pictured myself alone. I’m not afraid to be alone; I would just prefer not to be. Yet the older we get, the more often I see my friends operating on a solo flight through life. Some choose that path; others just accept it as their fate. Like many things, I think the opportunities to find that someone change as we get older. In high school or college you had parties and activities and a seemingly endless pool of candidates. As an adult, you have smaller pools with more complicated consequences – you don’t want to date where you work, make things awkward amongst your friends, run in to them at your favorite hangouts, or be the creepy person in the grocery store trolling the produce aisle for melons and a phone number.

Plus, there is the rejection. There is always someone prettier, younger, richer, more successful, thinner. We feel broken compared to them. And then there is the fear: why does this person like me? What’s wrong with them? Why are they still single? They must be broken, too.

We are all broken,” Rocker points out to me a lot. “When you get to be our age, you are going to have a few nicks and dings and cracks. What you have to see is if both your broken bits work together or just make each of you worse.”

I kind of like that. In my head, I picture a wheel of four hands, each one holding together the broken bits of the other person’s spoke. I’ll have strength to cover you here, you have strength to cover me there. Together, holding hands, we’ll get through this journey.

I fail a lot. I look back at the past year and the men I’ve dated and the reasons why things didn’t work out. I’ve been lied to, cheated on, stolen from, and sugar momma’ed (is that a word?). I’ve flirted with men who patted me on the head and walked away. I’ve had others not even respond. But I’ve also made some great friends, had some fond memories, and told some funny stories. I’m not a natural at this dating thing – I’m sometimes worse than a noob. But I keep trying.

It’s worth it, y’know. Putting yourself out there. I know I’m in a good place right now, so it’s easier for me to say that. But this blog proves I’ve been in bad places too. You have to keep trying – working at it – failing at it – and trying again. May we all find someone else to hold hands with.