Cheers! Halfway Point

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 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.

What follows are the reviews and summaries of dates 20-25.

Kicking Fear’s Ass

A friend recently asked me why in the world would I would willingly subject myself to the discomforts of 50 first dates. To not only answer that question, but also help my friend really understand a component of my motivation, I had to ask him a question. “Have you ever been completely overwhelmed by fear? As in so consumed with feelings of anxiety that you would rather live a life that is absolutely inauthentic, rather than take a risk?” I asked.

I have. I was so afraid to leave my marriage; to raise my children alone; to manage on one income; and to admit that I had failed in love; that it was slowly debilitating me. I had made so many concessions to keep my marriage intact, that I started to forget which me was the real one, and which was the imposter.

Why had I wasted so much energy trying to hide myself, make myself smaller, be less passionate, ask fewer questions, and conform to values that I didn’t believe in? Easy, I was absolutely terrified of being authentic, vulnerable, honest, and ultimately rejected.

Until I wasn’t.

I woke up one day and knew that it was time to stop playing small, start the journey back to being me and to not only tell fear to fuck off, but to also make it my bitch. I was going to use fear as my fuel, and get so damn comfortable with it that it no longer had power over me.

Here is a fun fact about me! When I find an area of weakness within myself, I am willing to do whatever it takes to heal and grow, no matter how difficult and uncomfortable it may be. What I have learned is that growth happens when I am forced outside of my comfort zone, and when I’m pushed and stretched and forced to overcome challenges and self-doubts.

There are people who are perfectly content upon achieving a goal, and feel good with where they are at in life. And then there are people like me who upon achieving something, immediately start the search for the next challenge. In order to ensure that I didn’t fall back into old habits, I decided to challenge myself to do something that scares me every single day for 365 days.

I am finding my limits and blowing them up. I am putting myself “out their” over and over again on each of my 50 first dates, with the very real possibility of rejection and judgment. I am desensitizing myself to the hold that fear had over me and am looking it in the eyes and saying “fuck off”.

By facing my fears that live inside, I am slowly changing my reality outside.

If only becoming immune to social fears could also make me immune to shitty dates, I would totally be set!

50 First Dates

50 First Dates: Dates 21-25

Date 21. Dirk the Alphabet Boy

Dirk is a handsome man with sharp features and a very calm demeanor. With a deep baritone voice that I could listen to all day, I’m pretty sure that if he ever decides he wants to leave his position within the FBI, he could totally be a phone sex operator. A single dad to a beautiful little girl, he really is a great guy!

Yelp Review:
We met for drinks at a trendy little bar where we spent hours chatting. Dirk was extremely charming and had me laughing most of the time. He was easy to talk to and his naturally flirty personality made for easy banter and lingering looks. I enjoyed how he always kept his body turned towards mine and would find very subtle ways to casually touch my arm or bump my leg, turning the whole night into a slow-building of sexual tension. I was all too happy to accept his invitation to come back to his place. Overall I would give Dirk:

4 Stars ⭐️⭐️⭐️⭐️

What I learned about myself:
I have really enjoyed exploring chemistry and sexual attraction. It’s so funny to me how incredibly complex human sexuality really is, and yet how it is instinctual at the same time. Closely paying attention to my body’s physical response to other people has been really interesting, and I never noticed just how sensitive my sensory system is when it comes to building a sexual response. It’s so much easier to find myself turned on when my date smells nice, is aesthetically pleasing, has a nice sounding voice, and when we are consuming something tasty. I have had a kiss where someone had bad breath and it was a total mood killer for me, which I thought was so strange. How could one kiss totally make or break an entire three hours spent together? Luckily Dirk’s breath was fresh and minty, and I was all too happy to see where our attraction led.

Date 22. Taylor the Tourist

I don’t think Taylor is the kind of guy that many women would take a second look at, and not because he is ugly, but because he is very plain and just kind of blends in. A closet nerd with every known Star Wars collectible, Taylor has brown hair, brown eyes, and a bright white smile. He’s a man who pays meticulous attention to details and has a whole album dedicated just to his 3 cats.

Yelp Review:
Taylor decided that we would meet at the video arcade and play pinball, which I thought was kind of cute. The place serves beer and I think that perhaps my sweet friend had one too many, and unfortunately, he isn’t a fun drunk. He became extremely obnoxious and so I faked a headache and excused myself. Overall I would give Taylor:

1 Star ⭐️

What I learned about myself:
This was a rough date for me. The arcade was really loud and not my scene. I have taken my kids to the place many times, and although I can certainly appreciate and value of an adult who enjoys play, as a single mom, when I am going out the last thing I really want to do is hang out at a kid venue. However, I still could have enjoyed myself and my date had he not gotten sloppy drunk.

Now I will admit that I was torn about how to handle the situation. On one hand I have felt like an important part of my process is being authentic and honoring my truth by speaking up and communicating honestly and fairly, and on the other hand, I was dealing with a drunk guy who I don’t know and I wasn’t sure how he would respond to me. Deciding to be dishonest and make up an excuse felt shitty and like I wasn’t honoring my truth, but at the end of the day I decided that it’s ok to pick and choose who I have authentic interactions with based on whether or not I feel safe to do so. I think finding a balance of sticking to a commitment I make with myself, with being flexible when a situation arises and following what I feel in the moment, is just as valuable.

Date 23. Mike the Former Marine

What I first noticed about Mike was how bright his eyes are and how they held a glint of mischief. He’s an interesting combination of a type A personality and a great sense of humor. Average height and muscular build, he was easy on the eyes. I’m not sure where he got his fashion sense from, but his style was absolutely on-point and not what I would expect from a man who spends his day in a military uniform. He was previously a marine and now serves as a sergeant in the National Guard.

Yelp Review:
We met at my favorite Thai restaurant where my favorite jokester wait staff sat us at “my table” with knowing smiles. Our conversation vacillated between fascinating topics, and lewd stories of what it is like being in the military, both of which were equally interesting to me. I really appreciated and enjoyed the lightness that encompassed the whole interaction. Overall I would give Mike:

4 Stars ⭐️⭐️⭐️⭐️

What I learned about myself:
After having spent weeks communicating, I was a little bit nervous to see if we would like each other as much in person as we had over talk and text. It is so weird how I can develop a relationship with someone without ever meeting them, and yet how meeting in person can make or break whatever connection existed. It makes me wonder then if the connection was ever real. Can we synthetically create a bond just in our minds? How do we explain when only one person feels the connection and the other doesn’t? What is the difference between someone we do and don’t connect with? Fortunately, the connection that we had spent weeks creating made the whole evening feel comfortable and validated that the connection and familiarity was indeed real.

Date 24. Not so Nice Nick

In possession of a near permanent frown, it was hard to determine if his strong masculine features could be considered handsome or not. Dark hair and dark eyes, standing at 6 foot something, he gave off a vibe of formidability.

Yelp Review:
Nick invited me to a nice restaurant downtown so he could spend two hours of my life that I will never get back, telling me every single thing that his ex-wife had ever done wrong. I’m not exaggerating here folks. I literally know shit from this woman’s childhood, like the one time she threw a rock through the picture window of her dining room when she was 7. It was my first date where I was not asked even one, single question. On a side note, the Tom Kha Gai was absolutely stellar! Overall I would give Not so Nice Nick:

0 stars

What I learned about myself:
I learned that it is a lot easier to tune someone out after a strong Thai sunset from the bar. And I learned that being new to drinking, 2 drinks is really my limit. I have also learned that the wait staff at this particular restaurant purposely sits me at the same table every time I come in with a new date, as a joke. Well, the joke is on them. I actually love sitting right next to the window where every single person walking by can watch me eat my dinner.

Date 25. All Mark-ed Up

A 40-ish-year-old recently divorced, father of two who spends his days providing marriage and family counseling. He has an average height and build, with a classically handsome face and engaging personality. He gives off a vibe of being both bold and shy.

Yelp Review:
We met at a restaurant to have a few drinks and my initial impression was that he was very nervous. A good balance of giving his backstory, without bad mouthing his ex earned him extra points in my book. Our conversations were all over the place and we discovered that we had many shared interests. The restaurant was soon closing, and I happily accepted an invitation back to his house to watch a movie. We spent some time messing around on his couch, and I was put off by his very rough nature. Now don’t get me wrong, I enjoy a man who is passionate, but being left with bruises and marks without having agreed upon that up front was a major turn off for me. Overall I would give All Mark-ed Up:

1 Star ⭐️

What I learned about myself:
I will admit to being hesitant to go on a date with someone who works as a mental health provider, wondering if he would be analyzing me the whole time. I quickly remembered that we all analyze one another during a first date regardless of our professions and that I was being silly. It was an interesting opportunity, however, to take a look at ways in which I make preconceived judgments about other people still.

I really do try to give each and every new person I meet a fair opportunity to show me who they are without judgemental. I also try to factor in that nerves can be strong on a first date and that just because we didn’t have instant chemistry, doesn’t necessarily mean that the person isn’t still a viable dating option. However there are a few things that I consider to be fast and hard deal breakers that include, someone who is extremely negative, rude to wait staff, a smoker, disingenuous, or makes me feel unsafe at any point. Thanks to my new friend All Mark-ed Up, I can also add a new item to the list: someone who is so rough that they leave bruises on my body.

Thanks a lot, asshole!

On a side note:

Yippee! I am officially halfway done with my 50 first dates and have really learned so much about myself and dating after divorce! I have had some really great and positive experiences, some really fucking awkward ones, and some that I am simply happy I don’t have to repeat.

I love that I no longer feel the same gripping fear that I initially felt each time meeting someone new. I am pushing myself outside of my comfort zone, and am finally starting to really feel the growth each time I am able to confidently walk into a first date with my head held high truly knowing that I have so much to offer!

Dating is now an arena that I am a skilled player in and I can’t wait to see how this new found sense of competence will impact the last half of my 50 first dates.

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