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50 First Dates: Dates 36-40

No Always Means No

I 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. 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, which involves embarking on 50 First Dates! You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list) and has progressed up until now here.

Why Consent Matters: The Aftermath

Dear Reader,

This was by far the most difficult article for me to write thus far. I have shared very raw and vulnerable pieces from my divorce, dating, and sexual journey of exploration. I have shared funny, awkward, ugly, and sexy moments. I have, for the most part, tried to keep this sharing process somewhat light-hearted in content. Today, I am going to share the next five dates in my crazy, fucked up journey, one of which was extremely traumatic for me. I have gone back and forth about whether or not to share what happened, how much to share, or if I should just skip over it entirely.

When I started this journey, I vowed to do it on my terms, and in my own way. I wanted to be bold, brave, fierce, and authentic. I wanted to not only find my voice but also honor it by speaking up and unapologetically being true to myself. I wanted to find a way in which to document the process of learning to integrate all of the new experiences I was having, and find a balance between who I am and who I am becoming. My fear of skipping over something because it was traumatic, is that I’d be invalidating the realness of how messy life can be, and pretending like this process is something it’s not.

Getting Real & Fighting Fear

When we silence ourselves because we are afraid of the consequences, we perpetuate an abuse cycle that feeds on silence and fear. God forbid should my closest friends perhaps discover that I am not infallible, don’t always know what I am doing, and don’t always have my shit together. *Gasp…*  

We often feel like we have to present ourselves and our stories in a refined and polished manner that only showcases the things that are polite enough to discuss. I’m learning that there is so much value in being real, raw, and messy. And that when I stop trying to control the outcomes and the way things look, I am then able to free my mind and experience things that I in no way could have otherwise.

It’s been amazing to free myself of social constructs and live outside of the box in a hedonistic playground of debauchery. However, it is not without risk, and I have had to pay the price a time or two. I am working hard to not get lost on my journey, and one way in which I’ve been able to maintain my center has been through writing and sharing my story. Forcing myself to reflect on what I’m learning after each experience has allowed me to keep my focus where I intended it to be, and therefore it feels important to include everything.

One of the next 50 first dates (#38) is going to be a little different, and I would encourage you to skip this one if you’re triggered by sexually aggressive material.

50 First Dates

50 First Dates: Dates 36-40

Date 36 Dr. Dave the Delusional

Synopsis: Oh boy. Extremely tall. Extremely awkward. Extremely intelligent. Extremely weird. Like such a weird dude that he is comically the closest person, I’ve seen that resembles a real-life cartoon character. Think a mix of Goofy, Dr. Doofenshmirtz, Pinky, and Anton Ego. Dave insists on putting Dr. in front of his name as he is incredibly proud of his doctorate in chemistry. What pray tell does a man with a doctorate in chemistry do with such a prestigious title? Grows and breeds marijuana of course! Not just any kind of marijuana, but a hybrid breed that is taking the industry by storm….

Yelp review: Dr. Dave humorously responded to my tinder bio with an opening joke about how he would let me buy him dinner in exchange for being a subject in my social experiment. At least I thought he was joking… he wasn’t!

He sat down at the table 15 minutes late to our date and proceeded to tell me how he was going to order the most expensive drink and meal on the menu since I was treating him. To say that I was less than impressed with his rude and socially inappropriate behavior is an understatement. He really wowed me with his next conversation subject of ex-bashing, which is such a turn-off for me.

Dr. Dave ended strong by dropping the bomb that he had recently been diagnosed with aggressive cancer and would happily accept pity sex. I happily listened to him babble for an hour and a half, paid for his meal, and felt like more than a humanitarian for how gracefully I endured his company, without granting his concluding request. Overall I would give Dr. Dave the delusional:

0 stars

What I learned about myself: I have canceled dates, walked out of dates, made up excuses to leave early, endured dates, enjoyed dates, and treasured dates on my 50 first dates journey. Each date and each person has provided such unique experiences, and I really have tried hard to treat each as something special. I didn’t want to become disenchanted or disingenuous from just the sheer repetition of what I’m doing. I don’t compare my dates to one another; I walk in each time with an open mind and open heart. Sure there are some dates I look forward to more than others, but ultimately the moment I’m not willing to give another human being a fair shake at connection is the moment I stop dating and walk away for good.

I really tried to find a way to connect with this guy and to hold space and compassion for someone who is clearly struggling, but in the end, I really just couldn’t do it. Even though I couldn’t connect, I did feel like I could stay, share a meal, and listen without it causing any harm to me. I learned that sometimes that’s good enough.

Date 37. Electric Trevor

Synopsis: When Looking into Trevor’s striking blue eyes, it is apparent what a kind, gentle, good man he is. He is a lovely soul who comes across as a little shy at first, but upon warming up, is quick with an inappropriate, well-timed joke. Never one to seek out attention, ET is the epitome of humble. Delightful and unassuming, the man is blazing (and occasional stumbling down) his own unique trail in the world of nonmonogamous dating.

Yelp review: We met for late-night drinks at a restaurant that was in between our houses. I had absolutely no idea what to expect as our communication had been sparse and hit or miss in frequency. I was pleasantly surprised by how comfortable I felt with Trevor almost immediately. The restaurant was soon closing, and we had only had time for one drink as I had been running late. When he suggested that we continue our date at his place I gladly accepted the invitation. I could tell that he was very nervous, which I found both endearing and charming with him. Our flirtatious talking lead to kissing, our kissing lead to touching, and our touching lead to a delightful time in his comfy bed. Overall I would give Electric Trevor:

4 ⭐️ ⭐️⭐️⭐️

What I learned about myself: it’s funny how oftentimes I seem to learn the same lessons over and over again, and even though they are not new lessons, typically they are learned each time with a bit more depth. I know better than to ever judge a book by its cover, however, I am still human. Trevor comes across as a very average dude and does an amazing job of containing an immensely deep curiosity and passion for life.

Never would I look at Trevor and think many of the things that came out of his mouth would. I absolutely adore a good surprise, and he has proven to be one over and over again. Not only is he a hidden gem, but he is also as stable and steady as the mountains he loves. There is something about this man that calms the swift and ever-moving current of my soul. I love that I have been able to learn how to connect and appreciate another’s soul without any feelings of ownership, jealousy, or permanency. Trevor has taught me that a genuine connection without attachment is absolutely possible.

50 First Dates

Date. 38 Cuff Her Jimmy  (Trigger Warning)

Synopsis: He was a delightfully handsome and jovial police officer who was quick-witted and had a killer smile. Nearly 6 feet tall and broad in all the right places, with cool blue eyes and sandy blond hair, Jimmy had it going on! He was playful and cocky, with an underlying tone of competence derived from life experiences where he was the one to come out on top. His ability to fill in blanks with a relevant story to share made our time pass quickly and enjoyably.

Yelp review: We had dinner at a cool spot downtown that I really like. We filled our time sharing pretty personal information and building a cool connection. I’m not going to lie, alcohol was definitely a factor in my freely sharing about my fuck it list. Jimmy and I clicked and decided that we were going to move the party back to his house. When he pulled out a pair of handcuffs and asked if he could help me check something off of the list, I agreed.

After some great foreplay, I found myself naked, face down, and handcuffed to his bed, feeling very anxious/excited at this opportunity to explore yet another facet of my sexuality in relinquishing control. He asked if I was interested in exploring anal and I politely said, “No thank you.” He assured me that if I just gave it a try that I would totally enjoy it, and even though I had said no, he decided that he knew better than I did as he was very sure of his skill set. I freaked out and was screaming at him, and the next thing I know, his roommate was barging in, flipping the lights on, and asking what the fuck is going on.

It was humiliating and my only non-consensual experience on my 50 First Dates journey. Overall I Give Cuff her Jimmy:  

0 stars

What I learned about myself:

Honestly, I have spent the last two months really beating myself up over this experience. I felt so much responsibility for putting myself in such a fucked up position. How could I be so careless with my own safety and well-being? How could I think it was ok to explore this kind of boundary with someone that I didn’t even know? Why would I drink to the point that I did and then leave with a stranger? Who cares if he is a police officer, that doesn’t make him infallible, and I knew better!!

I was so incredibly disgusted with myself.

In his mind, I think he felt like he could help me enjoy something, even though I said, “No thank you.” Did he respect my boundaries? NO. Did he take the time to listen and really make sure he had consent? NO. He is responsible and accountable for his actions.

I am accountable for my actions and am aware that my well-being is always My responsibility, and I have vowed to not make this mistake again. From here on out I will only cross items off of my list that explores potential safety/or relinquishing control, with people that I trust and have built a relationship with.

I’m taking a stand and deciding how I want to engage in my experiences instead of trying to control the way another person chooses to treat me. This was a very traumatic experience for me. After this night, I honestly considered putting a stop to what I was doing. I struggled with locating that fearless badass chick who was so committed to her journey of self-discovery and exploration.

Ultimately I refused to roll over or to pretend this experience didn’t happen because it’s now part of my story, and there is value in it. It wasn’t happy, fun, or sexy, but it was real, messy, and vulnerable.  

50 first dates

Date 39. The Baker Bob

Synopsis: This man is an introverted, cat-owning, square glasses-wearing, bike riding, real letter writing, hardcover book toting, retro throwback who belongs in a different time period. An artisan baker by trade, a gentle soul by birth, and a delightful man in person, Bob is slow to speak, with carefully crafted words, and a voice that I could listen to for hours. Tall, heavyset, with extremely handsome dark features, and a uniquely vintage style, he is a classy dude. He may not turn heads, but anyone with half a brain can quickly assess that he’s a man worth taking a second look at.

Yelp review: After my previously traumatic date, I took a little break and decided that the best way to get back into my process would be with a day date at a coffee shop. We met at one of my favorite coffee shops/bookstores where we talked about philosophy, anthropology, religion, politics, culture, and how magically, browned butter can change any pastry from good to fan-fucking-tasking.

Bob was delightful, charming, and real. He openly shared that he is definitely looking for love and something serious, and in no way held it against me that I wasn’t ready for anything serious. We both agreed that our date would be a one-time thing and that if at the end of my journey, my heart was open to love, monogamy, and commitment, that I should look him up and see if he is still single. I love that I walked away without feeling judged or condemned, and instead, I felt heard and respected. Overall I would give The Baker Bob:

4 ⭐️⭐️⭐️⭐️

What I learned about myself: I felt confused and torn about how to proceed with dating after my handcuff debacle. On one hand, I felt a need to protect myself and honor my feelings, on another, I felt like changing anything I was doing was in some way giving my fears and trauma power over me.

It’s so hard to know when to push and when to support, or how to do both simultaneously. I have felt immense value and growth from this journey and wasn’t about to give it up, however, to continue to do things in the same manner also seemed unwise.

I made a decision to allow myself to slow down and catch my breath. I took a step back from many things in my life for several weeks to process, journal, reflect and fall apart. I cried. I was angry. I shut people out. I went through a whole spectrum of emotions on my own terms and in my own way.

I made the decision that I wouldn’t allow my experience to taint what I had already accomplished, nor would I allow it to make me close myself off to possibilities. I learned that I’m stronger than I knew, and I took that confidence with me into my next date. I loved that Bob and I were able to connect in such an authentic cool way and that I didn’t hold a bad experience against someone who wasn’t involved by being closed off.

I purposely picked someone who seemed very calm, kind, and docile, and it was the best decision I could have made. I learned that connection is always worth the risk and that pain is truly inevitable but that suffering is optional. I’m choosing not to suffer through divorce, dating, and searching for myself, through the power of acceptance. I’m learning to lean into the hard stuff over and over again because it is so fucking rewarding and empowering to be able to accept myself and my experiences.

Date 40. Jenna

Synopsis: With a bio that simply reads “Anything is possible”, Jenna is an open soul. She’s an extremely smart, funny, kind-natured gal who was looking for love in all the wrong places. She has bright blue eyes full of flirty fun, is tall, athletic, feminine, and beautiful. A dog lover who is happiest at the river with a beer in hand and sunglasses on her face, Jenna has a laid-back and cool demeanor, with an intrinsic need for adventure.

Yelp review: Jenna was only in town for a few weeks to help her sister who had just had a baby. She was so funny about giving me permission to write about her, but only if I also gave a promise not to talk about her with other people. A strange request that I was happy to honor.

We met for drinks downtown where we quickly hit it off. I was super attracted to her physically as well as mentally. I loved her quirky humor and gentle kindness. She was very open and honest about how little experience she had with being with women, and her desire to explore and know more about that side of herself.

Normally my rule has been that I stick with women with much more experience than me as I am so new to being intimate with women, but she felt like a compelling reason to break that rule. We went back to her Airbnb and spent the rest of the night exploring boundaries and bodies. Overall I would give Jenna:

4 ⭐️⭐️⭐️⭐️

What I learned about myself: I learned that Jenna’s reason for asking me to not discuss our experiences together is because she has really struggled with coming to terms with her sexuality. She has kept this side of her life very private and hasn’t even discussed it with her closest friends or family.

It was so interesting to see such a beautiful, confident woman struggle so hard with accepting herself. It caused me to really reflect on how open and transparent I have been in my own life. My mom, several close friends, and a few select family members know of my exploits and that I have explored with men, women, and both. I most certainly haven’t told my kids that I have dated women, however, that’s because I feel like I’m already asking a lot of them just to navigate through the divorce and having their parents start dating. I think that when the time is right, I will certainly openly discuss things with both of them, and hope that by doing so I will give them permission to be bold, brave, and authentic.


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Kelli Davis
Kelli Davis
She Explores Life Co-Managing Editor, newly single mother of two, educator by trade, lover of words, and self discovering junkie on a mission to find a new normal.
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