How dating reminded me of my (embarrassing) past

Last week my longtime friend, Sammy B, married a wonderful girl named Ashley. 








It was a fun night filled with food, dancing, and a bunch of wonderful people I don’t get to see nearly as often as I like. Our group of friends growing up was a good one. It warms my heart that most of us are still in touch. 

Since we don’t see each other often, we go through the usual interrogation process when we catch up…. 


“So, still living in the same place?”

“Where are you working these days?”

“Are you seeing anyone?”


That last one has always been my favorite. (And by favorite, I mean least favorite.) 

I usually was the single one in our group of friends, and that didn’t change as I got older. I watched in envy as the rest of my friends fell in love, went on dates, and had lots of sex. (Seriously. I wasn’t even cuddling with anyone. It was so unfair.) Which is why I was thrilled to report to them that, “Yup! I am seeing someone! Wanna see a picture?!” 

Don’t get me wrong. I haven’t discovered any “secrets to dating.” But the whole night made me discover something: I used to be pretty unhappy with myself because of my dating story. And that night – none of it mattered. Hell, some of my friends I used to envy were currently single themselves!  

We waste far too much time and energy beating ourselves up, don’t we? 


We aren’t making a certain amount of money.

We aren’t married with kids. 

We haven’t reached a certain point in our careers where our dream job is paying the bills. 


But here’s the thing: Unless we’ve reached a point where it’s literally impossible to achieve our goals (Too old to have kids, etc), we can still get there. It just might take longer than we hoped….Oh, and it usually does. And the deadlines we place on ourselves are so unfair and silly. But that’s for another blog.

And here’s the best part – once we get there, that “embarrassing” past – which is really nothing to be ashamed of in the first place – isn’t going to matter. The point isn’t that you took longer than you thought. The point is that you got there. 

Friends. I have no idea when I’ll get married. All I know is that I will someday. (Not sure about the kids part….but if I do, we can cut go back and edit this part out, yeah?) And as long as that happens, I don’t need to be embarrassed about things that did or didn’t happen before getting there. 



We clean up alright 🙂 

Let’s go get ‘em, friends. 


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Thanks for reading!

By the way, I’m Tony. I live in Chicago. (Duh.) I’m an actor and blogger living right up the street from Wrigley Field. 

My blog is here to help others take control and live a more authentically positive life on their terms. Since working with a coach and learning more about personal development, I’ve started sharing my learnings with others. (I have a lot…)

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