I never thought I’d be a 50-year-old bachelor.

A classic Ask Jake. Plus, what I didn't say at the time…

Hey Jake,

I turn 50 next month, and so I’ve been doing a lot of reflecting. For the most part, I’m happy with my life and proud of the choices I’ve made. Except for one thing. I’ve never been in a serious relationship. My longest one lasted about two years, and that was over a decade ago. I date and occasionally hook up (when I’m lucky), but I’ve never landed on “the one”, and I don’t know why. It’s certainly not for lack of trying. All my friends assume I’m happy being single since I never talk about my love life with them (mainly because I DON’T HAVE ONE!), but the truth is I never thought I’d be a 50-year-old bachelor, and I feel like I’ve missed out on something special. Everyone always says “50 is the new 40,” and I know there’s still time, but part of me regrets that I haven’t found anyone yet and that if/when I do, we will have missed out on so many great years together. Thoughts?

Fifty and Forsaken

Dear Fifty and Forsaken,

Milestones are often a time to reflect, so it makes sense that you’re taking stock of your life. A lot of people say turning the big “Five-O” is one of the harder birthdays to grapple with. Even though I believe there’s truth to the cliche that “age is just a number”, I understand that 50 may feel a little different. Some might feel their carefree days of youth are over, and they’re looking at what’s next, what’s truly important, and how they want to spend the last few decades of their life (and who they want to spend them with).