Finally free!!! And failing miserably

 Dating After the Big House: Turns Out 'Experienced in Conflict Resolution' Doesn't Cut It

Dating in your 30s is like navigating a minefield of questionable bios and even more questionable fashion choices. We've all been there, right? The awkward small talk, the wondering if your outfit makes you look like you're trying too hard (or not hard enough), the silent prayer that you don't have spinach stuck in your teeth. Now, imagine that minefield is located in, say, a dimly lit sports bar in suburban Denver, and you feel like you're carrying a ticking time bomb, a secret you know is going to blow up your chances at any moment. That secret? My recent two-year stay at the Federal Correctional Institution in Fremont. Yeah, that's my life. Finding a connection with a regular person over 33 is harder than finding a date in Colorado who doesn't want to either go on a 14-mile hike up a mountain at 5 AM or Netflix and chill (and by "Netflix and chill," we all know what they really mean). Like, are there no other options? Can we just grab a coffee and talk about our feelings like normal people? Apparently not. But try throwing "former bank robber and addict" into the mix, and suddenly, your dating pool shrinks faster than your hairline right before your 24th birthday, even though everyone always told you that you got your hairline from your grandfather, and supposedly he had a huge head of hair. Well, maybe his real grandson got his hair, but it wasn't me.

At first, if I did manage to get a date (which was a feat in itself – seriously, I should write a self-help book: "How to Get a Date After You've Been on Dateline"), I would just rip off the band-aid. “Hey, what’s up? What kind of music do you like? Oh yeah, I just got out of prison.” I figured honesty was the best policy, right? Wrong. So, so wrong. Like clockwork, I would watch their eyes widen like I’d just confessed to showing up to the date with a six-pack of Keystone Light instead of the microbrewed Aspen-infused lager they were probably expecting. In Colorado, that’s practically a felony. Then the slow-motion jaw drop, followed by the “Oh, that’s…nice” with the same enthusiasm as someone describing a root canal. You know that look? That "I'm trying to be polite but I'm also calculating the nearest exit" look. Yeah, I saw that look a lot.

Then always followed by the frantic search in the purse for their cell phone (because, of course, it was definitely vibrating). And always some terrible accident or work emergency arose to save them from the nightmare they had seen too often on Dateline or, even worse and definitely accurate, Lifetime specials. You know, the ones where the guy has five secret families that he has to hide from his one new family because he just got out of prison, so he starts murdering people and running around with old acquaintances trying to pull him back into his old life… Yah, okay. I could practically hear the dramatic music swelling in the background. I half expected Chris Hansen to jump out from behind the Coors Light tap with a microphone. Or maybe he'd be behind a six-pack of Keystone Light – because, let's be real, that's what everyone in Denver is actually drinking. I mean, my mom used to be on the news, so I know how these things work. (Yes, that mom. The one who used to anchor the 6 o'clock news. Try explaining that on a first date, especially after you've already dropped the "prison" bomb. It's like a one-two punch of awkwardness. It's like saying, "Hi, I'm John. I'm a recovering bank robber. Also, my mom's kind of a big deal. No, really.") Speaking of which, you'd think someone would have mentioned my mom's local celebrity status while I was inside. Turns out, my "ride or die" friends were more "ride away and die of embarrassment" types. I got out, and it was crickets. Well, almost crickets. There was one person who kept in touch. My ex. The one who, during my incarceration, decided to dedicate her life to telling me, via very creatively worded letters, what a monumental screw-up I was. Think less "Dear John" and more "Dear You Are the Reason My Therapist Has a Boat Payment." So, naturally, when I got out, I thought, "Hey, maybe she's changed! Maybe she misses me!" I messaged her. She blocked me. Then, because the universe is a cruel but hilarious mistress, I found out she created a secret Reddit account dedicated to catching me in my "old ways." Which, to be fair, she did. And it totally made her look awesome. I'm not even mad. I'm impressed. And slightly terrified.

And while horribly terrible and terrifying that is, and maybe completely on point with some people, I had a great childhood, a really amazing upbringing. Seriously, it was all soccer games and family vacations. I went to college and worked at a few Fortune 500 companies doing marketing and B2B relations and lead prospecting before being in a string of car accidents. The last one? I was hit head-on by an SUV leaving a mini mall. The driver yelled out the window while I was on the ground gasping in pain, “Oh my God, hold on, I gotta pull over!” Which, in Colorado, can mean anything from “I just hit someone” to “I just saw a mountain lion wearing skis.” Turns out, it was the former. And they definitely weren't pulling over. They peeled out like they’d just robbed a bank, which, ironically, I would later do myself. (Just kidding…mostly. Okay, maybe not entirely kidding.)

But don’t worry, I got the license plate, and yeah, they definitely didn’t have insurance at all or a license. So even though you see all the lawyers on TV promising millions of dollars for your injuries, I got left with hundreds of thousands of dollars of medical debt, back pain, PTSD, anxiety, among other things, and a growing opiate habit to deal with all the pain I experienced. Goodbye corporate America and hello crime spree.

It's funny now, sort of. But at the time, it was just another reminder that starting over wasn't going to be easy. That the world saw me as a "former bank robber" and not as a person who made mistakes and was trying to move forward. It's a lonely feeling, you know? Like everyone's got their lives together, and you're just… trying to figure out which way is up. And that's just the dating scene. You should see what happened when I tried to get a job… (To be continued…)

And if you know of any really funny blogs about getting out of prison and failing miserably, please, for the love of all that is holy, let me know where I can find one. I'm thinking of "borrowing" their format. Okay, fine, stealing their format. Look, I'm a former bank robber, okay? Stealing is kind of my thing. Just kidding…mostly. (Unless the blog is really good. Then all bets are off.) Seriously though, hit me up in the comments. I need inspiration. And maybe a drink. Or ten.