50 First Dates: Commence Operation Get Laid!

dating

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! You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list), and has pogressed up until now here.

dating

Dating & Connection

A friend said something to me about how she assumed that once a person decided to get divorced, it makes relationships, in general, seem less permanent and less valuable. I don’t agree.  I’ve been asking myself this question this last week: “How has going through a divorce changed the way I value relationships and dating?” Sure, I know I can be ok without a man in my life. It is true, I decided to divorce my husband, but if anything my divorce process has taught me the value of relationships.

I think online dating perpetuates the notion that people are disposable—just swipe away and find someone better than the last! I have learned that a real connection is rare, so if you do manage to find one, nurture it. No one understands this concept more fully than a woman who has experienced the connection with her spouse deteriorate, fracture or be ripped away.

Even though I am having fun and not necessarily looking for anything serious during this dating adventure of mine, I am still seeking connection. It’s been really cool to connect with several different people without adhering to attachment or relationship models that I am not interested in currently. This has is a new dating experience for me.

During these next 5 dates, I certainly managed to make at least a few new fun connections. 

Dates 11-15

Date 11. Lazy Eye Isaac

Synopsis:
Depending on which side you are standing on, Isaac is a good looking guy! Not only is he attractive, but he has an impressive resume. He has worked in 6 different countries and is an expert in his field of bioengineering. It’s really too bad that that doesn’t help him with dating. I wish I could tell you how tall he was, or what his other redeeming qualities were, but he was incredibly shy and awkward.

Yelp Review:
Holy rusted metal Batman! Pictures just don’t do the man justice. Now listen, I’m not a judgy superficial bitch by any means, but when it takes serious brain power just to determine which damn eye to look at all night, you know that chemistry is not going to pop. But here is the other thing, if Isaac had been rocking confidence and swaging out every other advantage that he did have, I think I could have gotten over the one little flaw. His lack of confidence and inability to be comfortable made the whole evening just drag. Overall I would give Isaac:

2 Stars ⭐️⭐️

What I learned about myself:

I learned that I am over dating and am really just interested in sex at this point. The whole dating thing seems great in theory, but is time-consuming, awkward AF, and requires a skill set that I am lacking in my current sex deprived state. Perhaps I will be able to attract better potential partners if I am feeling sexier. And, perhaps I will feel sexier IF I START HAVING SEX! I think that the only way to get over the initial nerves of sleeping with someone that I am not married to is to just do it and see how I feel. Operation get laid is now fully underway!

dating

Date 12. Clayton & the Magical Cock

Synopsis:
A cheeky, lovable favorite—Clayton exists somewhere in the time continuum and he is on the spectrum. A Capricorn empath, with a quiet wisdom, lack of formal education, and gigantic—you never see this guy coming until he’s already gotten under your skin…and into your pants. He’s an unassuming man of average height and weight with precise features, soft chocolate brown hair, deliciously kissable lips, thoughtful bright eyes, and hipster glasses. He has a look of quiet seriousness, which changes when he feels relaxed or happy, into a smile of amused friendliness and pleasure. This arouses feelings of warmth, and something more, in many women.

Yelp review:
To call what Clayton and I did together a date is a bit of a stretch. Although I suppose it was a date of sorts. The sort that occurs behind the closed door of his bedroom, no clothes necessary. I found out I could have multiple orgasms, and I was sore for days afterward. Deliciously sore! He was an incredibly attentive, connected, skilled and attuned lover. I couldn’t have picked a better person to help me navigate this experience, and patiently guide me through all of my fears, insecurities, and discomforts. Overall I give Clayton:

5 stars ⭐️⭐️⭐️⭐️⭐️

What I learned about myself:
I’m not going to lie, having sex with someone who wasn’t my husband, for the first time, was one of the most terrifying things I have done. It took me a full hour to talk myself into actually following through with it and walking inside. We messaged back and forth for a few days and I felt a spark with him that I had yet to feel with anyone else. I also felt a sense of comfort with him that put me at ease. Nonetheless, I knew that if I didn’t at some point just take the leap, I would continue to get stuck in my head analyzing and not doing. Thank God I took the leap. I not only learned that I’m much braver than I thought, but I also learned new things about my body AND was able to cross things off of the “fuck it” list! It was hard for me to let go of many of my self-judgments, but in the end, it was exactly what I needed to do.

Date 13. Rick the not cop

Synopsis:
Rick is a quiet man with mysterious eyes, sporting dark blonde hair styled with a messy flair. Standing at close to six feet tall with broad shoulders, he walks with a slight limp. Rick gives the impression of having secrets, with his sly smile which makes you wonder just exactly what is he thinking about.

Yelp Review:
This man absolutely deserves the “best sport” award for how he handled being the victim of an online dating fuck up. I can’t even come up with a decent excuse for how I managed to absolutely botch and mix up this guy for another guy I was chatting with. He showed up at the brewery as arranged and after sitting down, I playfully asked him to show me his police badge. Here is where shit gets dicey…Rick was NOT the police officer that I had been flirting with for the last day and a half! I wish the floor could have swallowed me up. But, it gets better, instead of graciously apologizing and handling the situation like an adult, I totally turned around and walked out. After leaving, I realized that I had left my beloved water bottle behind and decided it was going to have to be a casualty because no way was I walking back in there. It was not my finest moment. Over all I would give Rick:

Three stars ⭐️⭐️⭐️

What I learned about myself:
I learned that I can in fact reach a new level of low in my occasional social awkwardness. I’m not sure why there are times that I seem to be able to push myself and other times where my well just seems to dry up with nothing left to draw from? Where was the strong woman who piled on lip gloss and swaged out her nerves on her first date tonight? And why did she abandon me in my hour of need? How come I can show up for myself sometimes, but not at all times?

I really need to get clear on how to harness and gain consistent access to this inner bad ass that I know exists within me. I have a sneaking suspicion that my life is a bit out of balance currently. I think that I have been too focused on dating and need to work on my other list as well—the one that includes things like: take a dance class, go to a movie alone, start buying red clothes again, and build a tribe of bad ass women to be in community with!

Date 14. Jamison the Beautiful Lumberjack

Synopsis:
A 6 foot tall, beautiful, ginger who sports a hipster vibe and a perfectly groomed red beard, Jamison has a disarming smile with perfectly straight white teeth, keen dark brown eyes and a sharp wit. He is a retired Marine war vet, who experienced real life hell, only to have his ex-wife show him how matters of the heart can be just as destructive. Although he is a gentleman through and through, he has a rebellious streak, sharp tongue, and an affinity for rough, raw, sex.

Yelp Review:
Jamison and I connected with an easy fluid banter online. Very little fanfare was necessary before we arrived at the conclusion that we both were interested in a simple no-strings-attached sexual relationship based on communication and transparency. It was fantastic to not have to go through all of the bullshit of pretending to want to date or pick out matching towels when it was obvious that we were both looking to scratch a sexual itch in a practical manner. We decided that we would meet in a public space for an “audition” where we sized one and other up and decided if there was chemistry. We had a drink and decided that we both had something the other person wanted. Over all I would give Jamison:

4 stars ⭐️⭐️⭐️⭐️

What I learned about myself:
Now I know this may not sound very romantic, but that’s not what we were going for. I learned that there is something incredibly sexy about meeting a stranger with the intention of having a purely physical relationship. At no point did I need to wonder what could be, or if either of us were developing feelings, which allowed me to really focus on the experience in a new way. It was also interesting in experiencing sex with someone who was incredibly aggressive in bed. Now don’t get me wrong, he was in no way violent, disrespectful, nor did he make me feel unsafe at anytime—but it was definitely a virility that was foreign to me. Sex is such an intimate way to connect with and experience something with another, and it’s been pretty mind-blowing to actually experience just how unique each encounter can be. I had no idea!

dating

Date 15. Billy Boy

Synopsis:
A Kenny Chesney look alike with an ego to match and talents that failed to warrant. He was completely arrogant, slightly judgmental and perhaps a bit mentally unbalanced as well. A 48 year old, recently divorced, part-time single father of 4 incredibly brilliant and perfect children he is an entrepreneur who owned his own very successful company and could “never work for someone else”.

Yelp Review:
Holy shit, this guy felt a need to let me know about his prestigious address at least 5 times within the first 10 minutes of our date, as well as the fact that he drove a blue corvette to our disastrous dining experience. Not only was he comfortable showing his ass, but he also made it a point to let me know all about his “Christian Faith” which allowed him to pass judgement on sexual sinners who indulged in alcohol and drugs far too frequently. Bizarrely, he got very angry each time fellow diners walked behind him to make their way to the restrooms. Like, he got seriously pissed that people would dare to walk behind him while he was eating, EVEN though it was the ONLY walkway to get to the bathroom. He in fact became so enraged that at one point he actually took the salt shaker off of our table and put it behind him in the middle of the walkway in an attempt to discourage people from using the walkway. Absolutely ridiculous! Over all, I would give Billy Boy:

1 Star ⭐️

What I learned about myself:
I learned that I am growing, yippee me! Old me would have allowed him to kiss me when he walked me to my car and leaned in for a lip lock. New me gave him my check and let him know that I appreciated his time, but would not be interested in a second date. I have gotten really great at being completely honest and have let go of the old bullshit belief that as a woman, it was most important that I be kind and not hurt someone else’s feelings. I now understand that as an authentic woman committed to sovereignty, I am NOT responsible for a grown ass man’s feelings and that the kindest thing I can do, is let him know exactly how I feel while being fair and honest.

Leading someone on by being vague and unclear is neither kind nor polite, and furthermore is withholding a growing opportunity for someone who could benefit in reflecting on how he behaved throughout the night! Growing into a strong, authentic woman is so fucking freeing and fun!!

Catch Up With These Stories

50 FIRST DATES, THEIR YELP REVIEWS & RECLAIMING MY IDENTITY AFTER DIVORCE

50 FIRST DATES: THE END OF THE BEGINNING

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