Rebuilding Rob

As WordPress continues to recycle old prompts, I pulled another prompt from The Coffee Monsterz Co to respond to today

Would teenage-you be proud of you today?

I think that overall, Teenage Rob would be proud of 2025 Rob. Of course, I’m sure there would be some things that Teenage Rob would be disappointed to see Rob 2025 doing, or not doing.

Teenage Rob might be a little bit surprised that I am divorced, I do think that Teenage Rob would just be excited to hear that 2025 me has dated women, been in relationships, been married, had kids. My divorce would probably surprise Teenage Rob though.

I think the Teenage Rob would be a little bit disappointed to see that 2025 me does not own his own home. Of course, Teenage Rob would have to understand that the economics of the world have change considerably in the last 35 years. Graduating from high school going to college and earning a college degree, do not necessarily equate lead to financial success. I do think that Teenage Rob would be happy to see that 2025 me is doing OK though, financially speaking.

Teenage Rob would be extremely proud to see that 2025 me became a teacher. Teaching was one of the first, realistic, and feasible goals that I had for a career. It’s what I went to school for. And through all the ups and downs of my academic career, I never lost sight of this goal. I’m proud to say that I made it happen. I think the Teenage Rob would be proud too.

The wisdom that Middle-aged Rob has accumulated through life’s experiences would certainly impress Teenage Rob. Also, he would be would be absolutely floored to see how confident 2025 Rob is. Teenage Rob would be confused as to what happened to the quiet, insecure Rob, who looked at his feet as he walked through the halls in high school. The younger me didn’t ask girls out – not because he feared rejection, but rather he feared being laughed at.

Finally, and I’m not saying this is going to sound chauvinistic and shallow, but Teenage Rob would be absolutely ecstatic to learn that Middle-Age Rob went out with Boss Lady a couple times and ended up sleeping with her. It didn’t go the way I would have liked, but it happened. I slept with a woman whom I was literally fantasizing about in high school. And she still looked great!

I’ve tried to imagine this scene in my head. I travel back in time and walk into my old high school. I see Teenage Me leaving my 5th hour journalism class – and timing it just so I see teenage Boss Lady in the hall.

2025 ROB sees TEENAGE ROB looking across the hall at teenage Boss Lady. I pull Teenage Rob aside:

2025 ROB: Hey, that girl you were just looking at…

TEENAGE ROB: I don’t know what you’re talking about.

2025 ROB: Yeah you do. I see the way you’re looking at her. (PAUSES) You’re going to sleep with her one day.

TEENAGE ROB: Yeah, right?

2025 ROB: it’s going to happen. It will be about 30 years before it does but it will happen. And she’s still gonna look great then too!

(TEENAGE ME tries to hold back a smile)

2025 ROB: You’re gonna be okay, kid. I promise you things will only get better after high school.

AI art courtesy of artist.ai

Thanks for stopping by Rebuilding Rob. Be sure to like, 👍 comment and subscribe to my blog below. It’s greatly appreciated! Also, feel free to follow me on social media as well! Check out my most recent posts as well as some earlier, related posts

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The article “Middle-Aged Rob Meets Teenage Rob” first appeared on Rebuilding Rob.