Catching Feelings Again
recently decided that reentering the dating world, after the disintegration of my 15-year marriage, wasn’t humbling enough. I thought I could really step up my game by also writing and sharing a “tell-all memoir” documenting my process after committing to 50 First Dates. I’m sure it sounds odd to hear that I am on a journey of self-discovery through the most unlikely source—online dating—but I really truly am committed to finding myself during this adventure!
You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list), in my previous article. It also reveals how I came to the decision to write a character synopsis, a yelp review, and what I learned about myself after each of my 50 First Dates, along with all the gritty details from my first five dates.
50 First Dates &Falling in Love with Potential
It is amazing to me how one moment can completely change so many things. I’ve worked really hard to become unfuckwithable during my journey. Not an easy task to keep one’s self-open to connection, but I’m impenetrable in my resolution to see things through. I want to maintain a growth mindset, but also remain rooted in my intentions. It also turns out that I am human and completely susceptible to stupid hormones, lust, and romantic feelings.
I’m ashamed to admit that I caught some feelings and got momentarily twisted up in the game. I fell prey to the rush of amazing sex, great endorphins, a shit ton of fun, and well-practiced charm. When I say twisted up in the game, I mean that for the first time while on this 50 First Dates journey, I started looking at what my long-term game plan might be. I wasn’t fully focused on the present—I was worried about how long it would last.
I even found myself begrudgingly accepting dates with my heart only half in it. I stopped wanting to sleep with new people because I was so satisfied with the sex with the current person. And here is the kicker, I’m not even sure when or how it happened!
It didn’t matter that I knew he was not up to the task of being a partner to me. It didn’t matter that several people warned me not to develop feelings for someone who was only meant to be a good time. It didn’t matter that I knew he could never love me the way I deserve to be loved. It didn’t matter that I knew he didn’t have the courage necessary to face his own stuff without judgment and was instead stuck in his past. It didn’t matter how many times his actions and lack of thoughtfulness were the cause of my tears.
None of it mattered, for I had made one of the silliest mistakes a grown woman can make…I had fallen in love with potential.
The Real Deal, Dates & Discovering What I Deserve
A huge piece of my journey of self-discovery is a commitment to being honest with myself and to take a deep look at what comes up, no matter how hard it is. I have learned that I am so desperate to continue believing that the world is the wonderful place that I want it to be, that I’m willing to simply overlook the ugly reality from time to time.
This is a dangerous thing to do when it comes to relationships. When I am willing to overlook the truth in order to continue doing something that is fun but not in my best interest, I have a serious problem. When I am centered
Date 41. Bro-D
Synopsis: Bro-D, the boy who will never grow up, has beautiful brown eyes lined with thick dark lashes, that are the center point of his beautiful baby face. We’ve all run across men that are delightful in their ability to live in the moment and engage everyone around them: the life of the party, token frat boy that will regale you with his tales from the weekend and have you feeling as if your life is dull in comparison. Bro-D always has the perfect shoes for each outfit and believes that the way into a woman’s heart, or her panties, all start with the shoes he wears. CrossFit has given him a muscular and deliciously solid physique, and his sharp wit and quick tongue make him a perfect sparring partner for sexual banter. If ever you find yourself lacking self-confidence, hope he is your neighbor, for surely he has more than an extra cup he could lend you.
Yelp review: Have you ever met someone that you felt both drawn to immediately and intrinsically knew they were absolutely trouble and would cause you harm? Well, for me that would be Bro-D. Bro-D was so incredibly engaging and the attraction and chemistry I felt straight out of the gate with him were intense. We met at a fun trendy bar downtown where we quickly entered into comfortable banter. He was handsome, but more than that, he had a keen intellect that was constantly stoking the simmering attraction and curiosity building between us. I adored his ability to make jokes and reply in a sarcastic yet relevant way to the things I said, and I couldn’t help but wonder if his sharp tongue would be as arousing in other ways.
When he asked me if I’d like to go back to his place, I found myself not hesitating for even a moment to question my loose morals and gladly accepted the invitation. Upon arriving at his house, as soon as we got inside, we stumbled into walls as we passionately kissed and groped one another in a mad dash to remove clothing. I loved the way he forcefully tossed me on his bed and ripped my pants off like he was a starving man, and I was his last meal. To say the sex was explosive and passionate would be an understatement. Overall I would give Bro-D:
5 stars ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
What I learned about myself: This is the first time I have ever been tempted to go back and change my initial yelp review. When I came home from my date with Bro-D, as I always do, I wrote my review and it was reflective of the time we had spent together just for that first date. As time has gone on and I’ve had more interactions, I’ve learned that there was more in play that first night than I was originally aware of.
I later found out that Bro-D had a bet with his roommate about whether he could fuck me within the first hour of meeting me. What I had interpreted as great chemistry had turned out to be nothing more than a bet. I felt foolish, used, and completely disposable. It’s so funny how just a tiny piece of information can completely change how we experience something. Just this one piece of information took what had felt like such a cool connection and turned it into a game.
For the first time in a long time, I didn’t feel like an empowered woman having an amazing journey of exploration, I felt like a silly naive little girl that stupidly bought something someone was selling, that I neither wanted nor needed. I had buyer’s remorse, felt like my heart had been run over, and seriously considered just calling the whole thing off.
But fear not, it only lasted for a minute, and after a solid night of drinking, several self-pep talks, and some really amazing orgasms, I came back to my senses. I concluded that I would simply see this as yet another life lesson and use it to get tougher, stronger, harder, smarter, and wiser. I wouldn’t build another wall around my heart, but I also would be more careful with allowing myself to be swept up in sexual chemistry moving forward.
Date 42. Don’t Touch Her Butt Roger
Synopsis: A quirky, bizarre individual with an interesting self-deprecating sense of humor. Roger is a recent transplant to the area who was still feeling his way around making friends and connections. A 30-year-old who acted much more like an old man, complete with statements like, “Wow this bar sure is a hip place that all the cool kids are at tonight”. Sporting a dad’s bod, a lack of self-confidence, and an inability to hold back on the things that he’s thinking, make Roger quite the character.
Yelp Review: After an award drink and an hour of a rather drab conversation, we decided to walk down the street to play some pool. The first time Roger spoke in the third person aloud, I really thought that he was just making a joke. He mumbled, “Don’t touch her butt Roger,” and at first I thought maybe I had misheard him, so I let it go.
The second time as I was leaning down to take a shot, and again I heard him mumble to himself “Don’t look down her shirt, Roger.” Now at this point, I realized that I had absolutely heard him correctly and that he was indeed speaking to himself in the third person aloud. I decided that although it was super weird, he was harmless enough and that I could order another drink and finish out the pool game.
The third time he let one slip, “Stop sniffing her Roger,” I finally lost it and burst into laughter, because come on! That shit is damn funny. He was taken a bit aback by my uproarious and unexpected laughter, and I didn’t have the heart to say a word, so we both just let it go. Overall I would give Don’t Touch Her Butt Roger:
2 Stars ⭐️ ⭐️
What I learned about myself: Ok, here’s the thing, everyone has little quirks and oddities and I am a very tolerant person. Working in Special Education has really allowed me to not only embrace odd but truly celebrate and adore it. Poor Roger was just a little too odd, even for my tastes. But, with that in mind, I was able to shelf that and have an enjoyable if not comical night.
I find that my tolerance for adults in social situations has grown immensely during this journey. Being on the other end, and starting out feeling super uncomfortable, has allowed me to have great amounts of empathy for others. Now, disrespect, rudeness, or negativity are a completely different matter than a person who is just super awkward in a dating situation.
I feel like there is value in holding space and staying engaged in a date through to the end of it and being one of many people who will hopefully give someone the opportunity they need to expand in their skills. Lord knows that there are those who endured me during my start.
Date 43. Honest Hector
Synopsis: An old soul through and through, Hector is a man who wears a newsy cap and tweed jackets with elbow patches that cover a broad and deliciously sculpted chest. He stands over six feet, with an incredible physique and an open, honest face. Hector is a gentleman who wears his heart on his sleeve, and the tally of every offense he has inflicted on his heart. A wilderness therapist for wayward teens, a second-time divorcee, and a single father of two, he is just stumbling through the process of coming to terms with failing at love.
Yelp Review: Hector had been very honest from the get-go with me, letting me know that he felt in no way ready to start dating again. He was however very curious about my 50 first dates and wanted to know what it was all about. After texting, messaging, and talking on the phone, he asked if he could read my articles, and I agreed. Upon reading the first one he decided that he wanted to make his own Fuck-it list but was still not sure whether or not he was ready for sex. It was almost painful to watch this poor man struggle with having biological needs unmet but warring with the notion of using another person.
He couldn’t imagine having sex with someone he wasn’t in love with. Eventually, we decided to meet for coffee just to talk. He was so sweet in his nervousness, and I absolutely adored his brutal honesty. We had wonderful conversations that were very personal and went deep straight out of the gate. We both acknowledged that we were attracted to one another, but would most likely not do anything about it. It was a very curious and interesting opportunity to engage differently. Overall I would give Honest Hector:
4 stars ⭐️ ⭐️ ⭐️ ⭐️
What I learned about myself: This was a lesson that I really enjoyed learning! I have loved having an opportunity to meet people where they are at during this crazy journey. It’s absolutely amazing to me how vastly different every single one of my 50 first dates has been. Some are based on intellect, some emotions, some sexual, some easy friendship, and others companionship.
I’ve been both a student and teacher in many of my experiences. I love that I have had so many opportunities to hold space for others and have allowed others to hold space for me. I’m learning about reciprocity in its most primal form and am finding that I adore the process of becoming more fluid and letting go of expectations.
If Hector needed someone that he could sext with and share with then I was happy to have that be the extent of what our relationship was. I have loved being able to engage with others, knowing that their journey isn’t mine and that I don’t have to take anything personally.
If I’m someone’s cup of tea—great! If not—great! There is no pressure to force things or attempt to control the flow. I’m learning to lean in and soak up all of the feels—and then lovingly release them. It’s such a liberating way to engage in life and I’m finding great joy in my ability to practice it!
Date 44. Making the World Smaller with Jeff
Synopsis: Adorable, sweet, funny, kind, and caring Jeff! A cutie 28-year-old personal trainer who hasn’t mastered the art of hiding his thoughts and feelings from his facial expressions, Jeff is athletic and handsome—and so brutally honest. He’s a breath of fresh air. An ambitious and bold man who doesn’t let fear drive him or keep him from going after what he wants, he is surprisingly deeper than what first meets the eye, with a fresh perspective on a lot of things. Jeff is a great conversationalist who kept things light and funny.
Yelp Review: Jeff showed up a few minutes late to our dinner date but was quick to apologize. I was upfront with him and immediately let him know that we had a mutual acquaintance and we laughed over that. When he inquired who our mutual acquaintance is, upon hearing the name he said, “Wait a minute, I know who you are!!! Your _blank_’s 75 dates chick! I heard all about you.”
I asked what exactly he had heard and he got very quiet and wouldn’t give any further information. I got a phone call, and while I was on the line he texted his brother letting him know that he would never guess who his date was, upon hearing who it was his brother texted back “Run bro, she’s gonna blog about you.” I realized in that moment that the dating world had gotten a whole hell of a lot smaller in my little town.
Pushing past that, we actually had a great time and spent much of the night drinking, making out, and laughing. Jeff was great fun, and overall I would give Making the World Smaller with Jeff:
4 Stars ⭐️ ⭐️ ⭐️ ⭐️
What I learned about myself: I definitely had a moment of feeling self-conscious, realizing that I now had a reputation. At that moment I understood that I had a decision to make. I could either allow other people’s judgments, opinions, thoughts, questions, comments, and concerns to infiltrate what I am doing, or I could swag it out and stay my course with my head held high remembering that I was doing what I’m doing with intent and purpose.
Who cares if other people think I’m making questionable decisions because damn it this is my life and I only get one chance to make of it what I will. Nobody else has to live my life or be me. Ultimately this whole damn thing is my very own choose your own adventure, and the only person I ever have to answer to is myself.
I am working towards saying goodbye to the old me that required validation and approval. I’m working on being authentic and following whatever experiences feel important and/ or relevant to my journey—Unapologetically. When I step into my own personal power and am able to love and validate myself, my experiences just become learning opportunities that need not be judged or critiqued, only valued and celebrated. They are mine, and for me to own.
Date 45. Todd Doesn’t Do One Night Stands
Synopsis: A strapping gent who strongly resembles the cavemen from the Geico commercials in both facial features as well as gravely tone, I’m sure Todd spends much of his free time in the gym as his bulging biceps would attest to. When he isn’t pumping iron or making commercials for Geico, he is a paramedic. At the age of 42, it seemed rare that he had never been married and doesn’t have any kids. He went on to share that he doesn’t believe in one-night stands or sleeping with someone on the first date.
Yelp Review: Todd and I had struggled with carving out a time that we could meet up. I’m not going to lie, my schedule has been fairly hectic with the amount of dating I have been doing. He texted me just as I was leaving a holiday party and inquired if I’d be interested in grabbing a drink. Since the night was still fairly young, and it had been a kid-free event, I found myself agreeing to just get one more date done.
We met at a bar that I hadn’t yet been to and found a cozy booth where we exchanged pleasant conversations for almost two hours. Todd had a great tapestry of life events to share and fascinating stories, and I found myself enjoying our time together. When he got to the part where he said that he was adamantly against one-night stands, he kind of lost me. I found myself initially engaging in the conversation and explaining my side when halfway through he told me he’d be willing to break his rule for me. I told him that I would never ask someone to go against their values. He attempted to backpedal and I found that very off-putting. Overall I would give Todd:
2 Stars ⭐️ ⭐️
What I learned about myself: Let me just start by saying that as someone who was in a very nearly sexless marriage for almost 15 years, I put a very strong value on physical compatibility in a potential partnership. I will never sacrifice a fulfilling sex life again. I repeat: NEVER again will I go any great length of time without a sexually compatible partner.
I have discovered that sex is very important and vital to my personal well-being. I am unapologetically a sexual being who adores intimacy and physical touch. I have loved exploring my sexuality and being a much more sensual being. I am actually a pretty big fan of first-date sex.
Now before you judge and condemn or slut shame me, hear me out people!
There is so much that can be learned by sleeping with someone that you have an interest in. Like, are they some weirdo who immediately gets up and has to shower three times in a row? Are they going to try to get you to budge on your mandatory condom pre-requisition? Will they hold you, or get up and get dressed afterward? Will they judge you or not respect you for doing the exact same thing that they just did: sleep with someone after a first date? Do they have weird hang-ups about what they will and won’t do? Are you compatible sexually?
Quite frankly, I have found it to be immensely valuable to get it out of the way and make a fast and hard decision about whether or not there is compatibility. I mean think about it…do you test drive a new car prior to purchasing it?