From ex-con to ex-lover

From the end of 2021 to November of 2022, I was in a relationship with an ex-convict. While I know that sounds crazy, he told me he was wrongfully convicted. Despite his innocence, he spent 15 years in prison. And the cherry on top of it all was I knew all of this before deciding to enter a relationship with him. I wanted to write my story in order to share what I learned from dating an ex-con.

When I first found out he spent 15 years in prison, my stomach dropped. My first thought was how hard it must be for him to adjust to society after spending so long locked away. I also started worrying about what or who happened to him while in prison. And then the thought of he hasn’t had the same life experiences that I have had came to me. But what I didn’t expect was how this would play out in our relationship.

The first few weeks were like the honeymoon phase. I couldn’t get enough of him. I was trying to see him every other day when I was off work and kid-free, and spending the entire weekend with him on my kid-free weekends. We would text often along with plenty of video and phone calls. Honestly, I thought I won the lottery. And despite his past, he was a successful professor about to get his Master’s in theology. The man spent Sundays preaching as a guest preacher at churches as well as grading and lesson planning. It didn’t even seem like he spent any time in prison.

Then things started to shift. First, he started comparing me to the person he created in his mind from reading this blog. Then he started comparing the first few weeks to the current time we were in. See, he didn’t have a car (yet), so I was the one driving to him 3 out of the 4 weekends in a month. Then, on the 4th weekend, he would complain about the long train ride he had to take to see me. I found it a little annoying but I continued to do my part and push on since I was starting to really like him.

Then in April, he got a car and broke up with me over text message while I was at work. He blindsided me, and I ended up crying in the staff lunchroom at work. I told him to send me the ticket to my graduation back in the mail. Hours later, he was calling and begging to let me talk to him in person. He came over, despite me not wanting him to since I had Aria. So, he met Aria and then explained to me how he took some bad advice from his ex. She had told him to break up to see if I would fight for the relationship. Since I didn’t “fight” the plan backfired and he regretted his decisions. Also, why he didn’t just talk to me rather than asking an ex for advice flabbergasted me. Unfortunately, this was just the beginning of our demise.

I can’t explain to you why I gave him another chance after the text message breakup. The only explanation I have is that I had fallen in love with him. And with the thought of our future together. And this wasn’t the only time we broke up. As time went on, he became harder to communicate with. Our phone conversations became very one-sided. It felt like I had to carry every conversation. He wouldn’t tell me much, and often it felt like I was trying to pry information out of him. As I became more vulnerable, he became more clammed up. He started giving me unsolicited advice on my life, lifestyle, and career/education goals. He didn’t like how much I socialized with my friends. He didn’t like how I prioritized things in my life. And he didn’t like that he wasn’t my top priority.

Things started to fall apart once he claimed that he was doing all of the work in the relationship and I wasn’t nearly close to putting as much into it as him. He felt like he was doing most of the driving, kinda like how we started the relationship. And he was right. I felt like a nuisance to him. He would tell me that he felt he was doing everything right and as much as he could for the relationship, but that I just wasn’t. And then my marathon happened. He knew about it, and I had invited him to go with me. I even paid for a hotel room and took Southwest all in hopes that he would join me. But when the time came, he never even tried to go. When I got back, he finally told me that he had never wanted to go to cheer me on. He felt he had shown up enough in my life. But for me, it wasn’t enough.

So I broke up with him. I had high hopes that we could be friends, so I asked for him to give me time to process and heal. Time away from him. I told him I needed a break in communication. But unfortunately he couldn’t respect my wishes. He kept reaching out. First through text, then email, then Facebook messenger. I had to block him on every platform just for it to “stop.”

It’s unfortunate, but in hindsight I should’ve seen it coming. I should have thought more about how his time in prison affected not just his lack of social skills but also his ability to mature naturally. I think his career and educational successes lured me in. Then, when he bought a car and a condo, I really thought he had it all together. But when he didn’t trust me enough to hang out with my running friends, I started to see that he didn’t have it all together. When he didn’t respect me enough to listen to me and my wishes, I knew I wasn’t dealing with someone on the same level as me. My only regret is not leaving sooner.

I guess this is what I get for giving the underdog a chance. I’m wondering from my readers, have you ever dated an ex-con? And how did it go? Or would you? Am I crazy for even giving him a chance?

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Technology is the death of romance

As some of you may or may not know, I have been on the struggle bus of romance for most of my adult life. The past year I’ve spent pursuing someone I kept telling myself was worth it. But in reality, I should have ran away when he dumped me via text message the first time.

Technology has led to many issues in the world of dating and romance. First of all, there’s countless dating websites and apps that promise you they will find THE match of YOUR dreams. The endless swiping makes it seem like there is a bottomless pool of applicants, and with that idea comes the idea that if the guy in front of you doesn’t work out, there’s another potential match behind him. But the reality is that I have matched with the same 3 guys countless times, and they are still just as single as I am with no more potential than the last guy I gave a chance.

And maybe it isn’t technology, maybe it is just my cold, wearisome heart that has been to hell and back. Married, divorced, had a kid with someone who never saw me, been on countless first dates, even tried my hardest to see the best in people only to crash and burn. It might be me, but technology has killed what little romance was left in my life.

Email or text message break ups are a cop-out. They are the cowards way out of a hard situation. I know because I’ve been that coward. It seems easier to just text. Easier than a phone call or face to face conversation. But even my first boyfriend who cheated on me had the decency to break up with me in person. And while that was uncomfortable and awkward, it was still 100 times better than a text message break up.

Despite my struggles, I am still pushing forward and focusing on myself and my happiness. But I think it is important to look for both green flags and red flags when meeting people. So I will leave the top green and red flags I’ve seen in the world of dating and meeting people when it comes to technology

Red flags:

Always on their phone/can’t pry their eyes off of the their phone on a date

Is more concerned about their social media accounts than actually making connections (guys and girls who just want the insta followers and not to actually date)

Prefers to text/email over having an actual conversation via the phone or face-to-face

Green flags:

Puts away the phone and keeps it away unless using to show you videos or pictures

Makes you feel more important than any device

Prefers to talk via phone or face-to-face and makes an effort to create those conversations as much as you are

Breaking out of the cycle

I know I haven’t written in awhile. I have had so many things on my mind to write about, but I was stuck in this cycle. This cycle of dating people who were just there to fill the void. Time-wasters. I kept trying to date the same type of person. The person that wasn’t emotionally available. The person who wouldn’t open up and be vulnerable so that I wouldn’t have to be either. Win-win. I kept telling myself that I wasn’t ready for a real person who would be good for me. I wasn’t ready for that person that God told me He has for me. I just kept pushing anything real away, and also anything too fake. I was in a cycle of going on 1-3 dates then dumping whoever it was that didn’t meet my expectations of a placeholder in my life.

I was dating two people a few weeks back, and realized that neither of them were anything close to what I wanted – what I deserved from a partner. I ended things with both of them and was nearly done with dating completely. I met a cute guy who rescheduled our first date 3 times, someone who I could tell upon meeting wasn’t looking for a serious relationship. A part of me thought he’d make a great placeholder. But something in my heart knew it was all wrong. Then I won the lottery.

See, I think dating is like playing the lottery. You will often bet your money but most of the time not be a winner. You might get lucky, win a few bucks, only to bet more and lose. But I am a hopeless romantic and I end up betting over and over again, in hopes that one day I strike it big. And have a reason to stop betting on all the wrong horses. Every time I’m on a dating app, I am hoping to find a reason to delete the app for good.

While I was giving time to emotionally-unavailable placeholders, I lost sight of what I really was searching for: a partner who would add to my life in a positive way. Someone who would be an asset to me as I would be to them. Someone to push me to be better than yesterday. Like I said, I told myself I wasn’t ready for this. Or started believing that maybe that person just didn’t exist for me. Because trust me when I say there are a lot of bottom-feeders in the sea. But what I was doing was looking in all the wrong places. I was looking down when I should have been looking up. I was in the wrong lane, the one full of the wrong people.

Now I feel my mindset and actions making a shift. No longer do I have time to waste with time-wasters. No longer am I interested in the emotionally unavailable. Now is time for Jen to be real and demand the same from her partner. Now is my time to seek companionship that brings even more joy and positivity to my life. Someone that puts God first just like I do. Someone who will not only support me and my dreams, but also push me to be a better version of myself. Someone who will grow with me spiritually, emotionally, and physically. I am ready for the person God told me about back in late 2016.

Healing is a journey

I wanted to write another post about partnership and what it is I’m looking for in life, but then I realized my last post was kind of a cliff hanger, so I am here to update you all.

First of all, I started therapy. Honestly, I am not sure why I ever stopped therapy and am I so glad to be back on my healing journey. Secondly, I was able to navigate and create boundaries that were necessary with the person I mentioned in my previous post. While there have been more tears and hard days since, they are getting more manageable as I focus more on myself and my healing.

While I know healing is a journey and I am just now re-starting it, I am already feeling less triggered and more centered on my wellbeing. I’ve been taking time to pray, meditate, and manifest what I want out of life. And, honestly, my social life has been exploding. I have been growing my network in and around Oak Park. I started a single moms and dads social group that has expanded to local singles. It went from once a month thing to a weekly meetup (but not on the meetup app haha). I have been coaching a running camp with my students at the school where I teach, in addition to teaching summer school. I have been training for the Chicago marathon and meeting new friends through different local running groups. I have been tutoring about 4-5 students a week for ACT or SAT. I’m about to travel to visit one of my best friends and get some much girl time with her. I’ve been living my best life with my daughter Aria as well. She tends to join at least half of my runs, and has been even enjoying the after-run beer with us! Just kidding, she just sips on her juice or water and eats all of the cheese sticks haha.

All of this to say, I am feeling fulfilled and full of joy these days. I am in a career I love. I am working towards that 2nd Master’s degree and more than halfway there. The only thing that I would love is a healthy and beneficial partnership.

That’s where I’ve been manifesting and I saw this post the other day on Facebook that one of my awesome friends shared. A healthy partnership is something I’ve never had, but it is something I both desire and deserve. This is something I will be working towards preparing myself to be a good partner who both receives and gives the love I deserve.

What is one thing you’re manifesting?

Waiting for my unicorn

A lot of people ask me why I’m single. Why, despite everything going for me, I can’t land me a husband. Or boyfriend. Or a guy that makes it past one date if I’m being honest. It’s because I’m waiting for my unicorn.

My unicorn is basically a male version of myself. I want someone who’s just as ambitious as me. Someone who’s bettering himself everyday. Someone who has as much faith and hope in Jesus as me. Someone who is as active as me, both physically and within their community. Someone who’s supportive of me as much as I am of them. Someone who can keep up with my humor and make me laugh just as much. Someone who’s vulnerable and real with me.

Someone who communicates well, or at least as well as I do with them. Someone who is trustworthy and transparent. Someone who listens when I need them to. Someone who is full of joy in their life but would like the cherry on top (that’s me haha). Someone who is passionate about their calling in life and pursuing it (whether that’s their career, business, or something else).

Someone who rolls with the punches and doesn’t let situations out of their control drag them down. Someone who falls 8 times but gets back up 9. Someone who sees the glass as half full rather than half empty.

Someone who wakes up everyday and prays. Someone who chooses me and keeps choosing me. Someone who loves me as much as I love them. Someone who pursues God and His unconditional love. Someone who puts Jesus at the center of our relationship and life together. Someone God has prepared just for me.

Until I find my unicorn, I will happily be single. I’ve found everything else I want in life. And like previously mentioned, even if I don’t find my unicorn, I will continue to grow in the joy and love surrounding me. Thank you for reading about my unicorn. 🙂

The longer that I wait, the more selfish that I get

Lately, I have been taking some time to meditate and reflect on everything I have. The other day, I broke down crying because I am so tired of waiting. Let me backtrack. It was the year 2013. I got married to the person who I thought was THE person. You know, the one God had for me. I got married thinking this was it. Happily ever after. The marriage that lasted until one of us passed away. And hopefully continued in Heaven. Fast forward to three years later and I was proven oh so wrong. My husband got bored and decided to sleep around then leave me when he found some greener grass. Ever since, I have been on a roller coaster of healing. Add in a surprise baby with someone who has no interest in being with me and I am about 4 years single.

As I took the time to meditate on everything I have and how far I’ve come in 4 years, I am full of joy and pride. I know God has helped me to grow into who I am today. Everything in my life isn’t perfect but fulfills me. I love my daughter, I love my family, I love my friends, I love my career, I love my community, I love my life. I love myself. And I love God. He has been calling me and I have been answering His call in my life. I feel like I have purpose in life. One that I don’t fully understand or see, but I am working towards it daily.

What made me cry then? I am so focused on this idea that I married the wrong guy and I KNOW there’s the right guy out there for me. I just don’t know why he hasn’t found me yet. I word it that way because I know I can’t force my way into this. I just so so badly want to marry again and have another kid or two or three. BUT I don’t want to marry the wrong guy again. So I just have to tell myself to be patient, slow down, and chill.

To my single friends, what helps you stay focused and grounded? I want to focus on all the positive in my life and not keep stressing over the one tiny missing piece in my life.

Pic of me at work for effect:

2021: Not that 2020 won, but that we be growing

In my last post, I went over the highlights of 2020. For the record, I got that upgraded car on the last day of 2020, a Subaru Forester which has been a great addition to my single mom life with Aria. I also unexpectedly met another great addition to my life.

I started texting this guy during the first week of December, at the same time of him leaving Chicago for the holidays to spend time with his family in Texas. At first swipe, I expected absolutely nothing much like all of the other matches and conversations that were going nowhere. But this guy did something unexpected. He was vulnerable from the first conversation. I found myself finding a lot in common with him, and demanding video calls to make sure he wasn’t a catfish. Fast-forward three weeks later, he’s in Chicago and agrees to walk around Oak Park with me. 6 miles later, I find myself just more comfortable with him.

Here’s the thing, I didn’t expect this guy to enter my life. I didn’t expect him to be vulnerable and real with me. And while it’s been a little less than two months from our random text message conversation, it feels like we’ve known each other longer since we have been our real selves with each other.

I waited until recently to have him meet Aria. To be honest, I thought he would meet her then change his mind and leave. As a single mom with a growing toddler, I know kids can be overwhelming for someone who is kid-free. Surprisingly, he has gone above and beyond my expectations of him. He went out of his way to make a great impression on Aria. And on the flip side of that token, he has been very careful and reserved as to how to react to Aria when she is showing him affection.

While I have come very far in my healing process, there’s still thoughts that creep into my mind that I battle daily. I recently reached out to a close friend who said “Love (or relationships) is scary” and they were completely right. But I also feel that if you don’t give relationships and love 100% chance than you’re missing out.

Until next time, here’s a cute photo of Aria being goofy.

Sifting through the garbage

Back by popular demand. I am here to update you all on the dating life of Jen. A few weeks ago, in a moment of weakness, I downloaded the dating apps again. After finally letting go of St. Louis (sorry Cal), I found myself a mixture of bored and buzzed. So what better solution other than swiping through other bored people in the middle of a pandemic?

The reality of it all? I had to deny and reject several offers before finally, weeks later, meeting someone. But up until that moment, I really thought I was literally sifting through a landfill. See, there were guys asking me if I’d give them a blowjob on the first date (true story). And there were guys sending me unwanted dick pics with no warning.

There was also this guy who never called me despite me telling him I wouldn’t meet him without a phone call first. He was so mad when he finally realized he was going kayaking alone.

Up until this past week, I really thought I was wasting my time. It felt wrong. All this swiping and texting for what? And with what pretend free time that I don’t really have? I was feeling overwhelmed and once again just wanted to run away from it all. But then there he was.

He seemed so simple and normal at first. The conversation was easy. Then we spent 5 hours on the phone and it felt natural. We met this past week for sushi, and once again it felt normal. Have I known him for a week or longer?

It’s all new but I’ve been praying daily for God to guide my footsteps. He told me, back in November of 2016, that He has “someone better” for me. I am really hoping and praying for my someone better.

Why I’m not afraid of being single

First of all, before I dive into the topic of my dating life, I must pre-cursor with: I am completely and utterly full of joy in every aspect of my life. My career, my education (on-going), my family, my friends, and my faith. Everything literally feels like a dream. Needless to say, I have zero complaints. Except for one. My singleness. But not enough to lower my standards. Or settle for less.

See, recently someone told me I can’t afford to be picky. Maybe because I have a daughter and want another kid. Maybe because I’m not getting any younger. Maybe because it would be really nice to have someone to help me grow in all aspects of life: financially, physically, and mentally. But no where in any of that is what God wants for my life. See, it’s easy to give excuses as to why I could just settle for the next guy who swipes right on me (if I ever go back on the apps lol). Or I could start building a case to go backwards and just accept someone who doesn’t value me as much as I should be valued. But in doing any of these things, I lose myself and what brings me joy.

Why should I walk away from my joy-filled life only to check a box? And while a good, healthy partnership is way more than a box, right now without that good, healthy relationship waiting on my doorstep it is just a box to check off. And at the end of the day, I have to focus on the most important things in my life. My daughter is important, my faith is important, my well-being is important. See, I love myself and I love Jesus. And I love others. I have so much love sometimes it’s overwhelming. But no where did God say it’s ok to love those who don’t love you back. Or, rather, you can love but with boundaries.

I think these past four years since my husband left me in late 2016 I’ve struggled with my self-worth and value. See, I believed the lies the devil told me that I wasn’t worth it. I still battle these lies daily, but I know that I am beyond worth it. I know that I am powerful but not powerful enough to ruin God’s plan for my life. And so far, from what I’ve seen, it’s a glorious plan. Even if it includes me being single. I have all the love and joy I need.

I’ll leave you all with this piece of wisdom:

Three strikes, you’re out

After my last post, things took a drastic turn for the worse. I won’t lie, I was totally smitten with this Doctor moving to Boston. I am not sure if it was Harvard, or all the punny jokes, but he swept me off my feet. Unfortunately, as I was developing feelings for someone who was about to move away from me, he turned into a 14 year old over night. All of a sudden, his mom wouldn’t let him out of the house (I could see why he was moving away lol). I tried to see him, but all of the excuses came up and it made me realize I was not as important to him as he was to me.

Moral of the story: don’t fall for a guy who’s moving away and knows he’s moving away and doesn’t tell you right away. Ugh, Boston, you got me!

I literally paused my dating apps, but once he refused to hang out with me again I went back. I met the third guy, who was cool until he told me he was legally married. Three years separated and supposedly hasn’t talked to his wife in three years, but I couldn’t see past the word married. See, I dated a married guy before and you know how that ended. In total utter heartbreak. I told him there was no way I could see past this. Also what the hell was he waiting for? Aaron Burr, if you stand for nothing, what will you fall for? Like if 3 years of no communication didn’t warrant a divorce, what would? AND why the FUCK are you on a dating app if you’re married?

To be a little nice, I agreed to be friends with him. But even that is iffy. He supposedly is calling a lawyer tomorrow, but I am still confused as to why he didn’t call them yesterday, or better yet three years ago.

Amidst all of this, another guy started talking to me. His profile stuck out because he used foreign words such as: He is dedicated, loyal, and loving. He was really cute and worked in a hospital. It was almost too perfect. He video called me and I agreed to meet him three days later. Right before we meet, I look up his dating profile and I realize he deactivated it. I’ve never seen this before, and it sticks out to me. We meet, and we talk, and I realize we have a lot in common. We have been through similar situations, and we have similar goals in life. He’s a year away from his PhD about to be a doctor/director of a hospital. To say he’s smart is an understatement. I won’t lie, this guy seems foreign to me. He legit wants to be with me after two dates. I deactivated my dating accounts and I’m giving him a shot. So I guess, wish us luck. I’m weary after Bright to be honest.

And the craziest part is I have two guys from a dating app who slipped through the cracks right before I met new guy who are quite upset I didn’t even give them a chance. But I am not able to date around. I am a girl who gives each guy a fair and even shot. So to the new guy and to us. Hopefully we survive Covid (I told him I want him to meet my church fam but obviously that’s not possible). I’ve been praying daily as I really do want what God wants for me. Whether it’s this guy or someone else, I am looking towards Him to guide my footsteps.

Stay tuned for more adventures in my dating life and beyond.