HomeDating50 First Dates: Dates 31-35

50 First Dates: Dates 31-35

Operation Rob the Cradle

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.

Connection, Attachment & Dating Younger Men.

The whole purpose behind my 50 first dates was always self-growth and learning. On my mission to really understand how dating and relationships work, I’ve striven to date a wide spectrum of characters. However, I recently realized that I’ve always dated or been attracted to people who are older than me and felt it would be remiss to allow a whole demographic to be left out. It occurred to me that I should try dating younger men. So without further ado, I give you 50 First Dates, Operation Rob the Cradle!

In one of the previous 50 First Dates articles, I make mention of the difference between connection and attachment. I have been clear from the beginning that this process wasn’t about getting attached to someone else, but rather about forming connections with lots of different people in an attempt to figure out how relationships, dating, and sex work best for me. A hugely appealing aspect of dating younger men was a theory that they would be less prone to seek out attachments with an older, single mother of two, allowing me to explore in the way I wanted while being fully present in the moment.

If I treat every date as “catch-and-release”, then I can allow myself to be completely transparent, authentic, open, and honest. Dating can be stress-free and enjoyable when I am fully present. I don’t need to waste energy or time worrying about whether or not the relationship is going to go somewhere, or if I am doing or saying all of the right things. Without that pressure, I have been able to really enjoy my time with each person, getting to know each other and allowing things to flow and unfold organically.

Older Women Dating Younger Men & Outdated Stereotypes

There are lots of stereotypes surrounding older women dating younger men. There is the whole “mommy issue” thing, and the “desperate older woman who can’t capture the attention of a man her own age” thing. All of that bullshit is outdated and overplayed.

Some younger men simply crave spending time with a woman who is confident, doesn’t play games, and knows what she wants. Some older women simply enjoy dating a younger man who hasn’t yet been jaded by horrific dating/marriage trauma, still wants to explore, and maintains the joy embedded within youthfulness.

This experience taught me that guys in their early twenties who haven’t been divorced, don’t have children or sexual performance issues actually have a lot to offer.

Because I adore lists, I  made one to encompass all of the pros that these young studs brought to the table.

The Pros of Dating Younger Men

  • They make you feel young
  • They love to experiment
  • They are less jaded
  • They are energetic
  • Less baggage
  • They’re physically more appealing
  • It’s empowering
  • It’s more about you
  • They step it up for you
  • They appreciate you
  • The sex
  • They are SO fun to date
  • They keep you up to speed with youth culture
  • They love your experience
  • Their attitude and energy are (joyfully) infectious
  • If you know what you want, they are likely up to the task

Feeling adored by an attractive, hot, young guy is tremendously exciting and good for the soul. I’m sure even reading this now you can imagine the fun you could have dating younger men. And boy oh boy did I have some fun with my 5, 20-something year-olds. But I’m not going to lie, there were moments when I had to really talk myself through trying not to feel like a pervert (and not offering them a fruit snack or juice box).

50 First Dates: Dates 31-35

50 First Dates

Date 31. Precious Pauly

Sometimes I really wish I could include pictures of my dates because they communicate so much more effectively than my words ever could. This 22-year-old, full-time student was absolutely adorable. Huge cheesy grin, black scuffed-up chucks on his feet, and a messy-hair-don’t-care vibe are just a few of the amusing first impression takeaways.

His almost six-foot-tall stature, broad shoulders, dark hair, dark eyes, olive skin tone, straight white teeth, and an Abercrombie wardrobe act as billboard advertising for Pauly as an all-American boy just starting out in the adult world. His personal hygiene was impeccable and he smelled absolutely delicious. He had an infectious laugh, easy demeanor, and outgoing personality, and he spent most of the night laughing, making jokes, and pulling others into our surface conversations.

Yelp review: After deciding that we were both looking for something casual and fun, Pauly invited me to a local brewery that was close to his apartment by the college to see if we had any chemistry in person. I was immediately attracted to his carefree easy smile and couldn’t believe how easily he shared it. Many of the men I had dated up to this point required quite a bit of effort in order pull that kind of a smile out of them, so I was of course intrigued. What did this kid have to be so happy about? It turned out that it was me!

Pauly was super excited to see me, and the first thing out of his mouth was, “Wow, you’re so much prettier in real life than in your pictures. I love a good surprise!” I was a little disarmed by his blatant honesty but quickly realized that it might just end up being one of the most delightful things about him. He was real and didn’t care about playing it cool. He was attracted to me, so he said so. It was mind-blowing! One drink turned into two, and two drinks turned into making out, and making out turned into deciding that we would get together again, but at his apartment next time. Overall I would give Precious Pauly:

4 stars ⭐️ ⭐️ ⭐️ ⭐️

What I learned about myself:
I learned that when it comes to dating younger men, there is a whole new level of casual dating that exists and that I totally dig it! Normally, I joke about being a small talk survivor. I gravitate towards more serious, deep connections and conversations. So imagine my surprise when I discovered that I loved that he didn’t ask me about my kids, or my job, or my divorce and instead wanted to find out what our shared interests might be.

We went through each other’s current playlists on our phones and laughed our asses off by the similarities and differences. It was super funny when his favorite playlist of mine was one that my son made titled “strictly for my homies,” and we both had a good laugh about the fact that he was closer in age to my son (8 years)  than to me (13 years). It was so fun to have this quick and easy connection, without feeling self-conscious about how I might be perceived—I mean, he’s just a kid, so who cares?! He was impressed by my wisdom and wanted to hear stories about the places I have traveled to or lived in. For the first time in a long while, I didn’t feel like a mother, or an ex-wife, or a professional, or a therapist; I felt like a new friend who had lots of exciting things to share.

Date 32. Wild Ryan

Every once in a while I meet someone who really takes their hobbies and passions in life and finds a way to have it encapsulate who they are as a person. Ryan eats, sleeps, and lives dirt bikes. He is extremely passionate about his dream to become the top Motocross racer in the world. In case you were at all confused about his priorities, his dining room contains not a table, but two dirt bikes in various stages of assembly. His average height and muscular build, scruffy facial hair, relaxed low-hung jeans, hoodie, and hair long enough to curl at the ends around his neck and hairline, give him an unkempt, roguish quality. He looks like a man who doesn’t give a damn what others think. He is not one to carefully pick or filter the words that come out of his mouth, making it a delight to discover just what may be said next. And, his 25 years of life have been spent being exactly himself.

Yelp review: Ryan invited me to the arcade downtown to play pinball and share some beers. This wasn’t my first date at the arcade, and although it isn’t my most favorite place to hang, it is something to do that doesn’t include sitting and sharing a meal (which I find overrated). So we met at the arcade and proceeded to chat while engaging in fierce competition for dirt bike racing domination (arcade-style). In which, I’m happy to report, I kicked his ass (in all four games)!

We were able to find some common ground in conversation because I grew up with dirt bikes and happen to love racing. I realized pretty quickly that, although Ryan was cute, fun, driven, and passionate, he was not my cup of tea. Outside of dirt bikes and video games, it was a struggle to get him on board with discussing much else. I knew pretty quickly that this would be a one-and-done date for me. Overall, I would give Ryan:

2 stars ⭐️ ⭐️

What I learned about myself:
Professional motocross riders usually compete in big national and international races, where they can win prize money throughout their careers. Having a paid sponsorship means someone pays them to use their products in competitions and wear their company logos. Ryan’s greatest accomplishment thus far in life is his recent dirt bike sponsorship, as he is one step closer to becoming a professional Motocross rider.

Professional motocross riders are athletes who have advanced to the highest level of competition in the riskiest sport. They are considered amazing athletes with exceptional physical abilities, endurance, and competitive instincts, among other talents; all according to Ryan. I love it when I meet people who will happily tell me how great they are if I ask. I’m not even being sarcastic. In a world full of people who lack self-esteem, originality, purpose, and confidence, it really is amusing to meet someone who has it in spades—regardless of whether or not I feel they have merit to warrant such esteem. When I grow up, I want to be unfuckwithable, and Wild Ryan has absolutely nailed that quality. I secretly admire that.

I’m sure that at some point he really will be a famous Motocross racer that I will see on TV, but unfortunately, that just wasn’t enough substance to make me want to either continue dating him or take off my clothes and hit the sheets with him.

50 First Dates

Date 33. Sean the Snowboard Bum

Despite looking and smelling a lot like a tramp (I suspect he actually is a tramp), snowboard bums like Sean will always be a hit with the opposite sex. This is usually because guys like him have learned that they need to live on their charm if they want to eat, and they’ve gotten rather good at it-the dreamy bastards.

Sean lives in a great house that he and eight other snowboard/ski bums all rent together and have completely trashed. Thankfully, his best friend’s dad is the owner, and his best friend is a trust fund baby. Sean is a rafting guide in the summer and snowboard instructor in the winter. He drives a Subaru that is held together with duct tape and dreams and drinks Pabst Blue Ribbon exclusively. He has an amazing afro, which he often sports a pick in, and an impressive collection of neon sunglasses.

As much as it is easy to look at him and dismiss him as someone with little ambition, who smokes way too much pot, he actually is a super kind and genuinely fun guy. Capable of conversing with anyone and laying the charm on so thick that it’s impossible not to get roped into his tangled web—he is ultimately harmless. He just wants to live and let others live. A gentle soul, with a huge appetite for what makes him happy; snowboarding, cheap beer, sex, smoking blunts, and women with dark hair and fast hands.

Yelp review:
Sean messaged me and told me immediately that he was intrigued by my 50 first dates idea and absolutely wanted to be a character in my story, on one condition… he wanted to be a sexy character. I knew right away that I was going to enjoy him for being funny, direct, and bold. I really like people who ask for what they want upfront without being crass and obnoxious.

I of course put this young guy through the paces, and he kept up just fine with my banter. We met at a shitty dive bar and spent time laughing and making fun of how different we are. He really was super charming and I adored the way he smirked; never smiled, always smirked. He kept a hand on my thigh or lower back most of the night, and made it clear where he thought the night was headed. By the time we reached his house, we were both feeling pretty excited about how the date would end. I have to admit that I don’t really understand how someone as young as Sean is as talented in bed as he is. It’s a great mystery.  But what wasn’t mysterious was the number of times he made me cum. Overall, I would give Sean:

4 stars ⭐️ ⭐️ ⭐️ ⭐️

What I learned about myself: I feel like I have really mastered the art of enjoying people for who they are, and celebrating the ways in which we experience life differently. I think it is so easy to fall into a habit of quickly assessing a person when we first meet and making quick judgments about whether or not they are someone we could be friends with, laugh with, learn from, be attracted to, converse with, care for, etc.

How often do we meet someone and simply listen? When is the last time you engaged with someone without any expectation of the outcome? Simply to learn more about another human being, not determine if they fit into a mold you’ve created for what’s valuable?  I’ve learned that joy can be found in the most unexpected places, sources, and moments, and it has renewed my love affair with life. Pretty deep shit can come out of cheap beers in a dive bar with a trampy snowboard instructor, if and when I’m actively engaged in listening and connecting.

Date 34. Baby Face Brandon

The sweet cherub-like cheeks and twinkle in his eye are a stark contrast to the words that come out of his fast-talking mouth. Being clean-shaven and well-dressed, but sporting a backward cap, makes no sense at first. He is youthful in appearance, yet has perhaps the deepest voice I have heard in real life. Brandon is a mechanic apprentice who barely graduated high school, yet has a robust and extensive vocabulary. While he was awkward in his ability to look me in the eyes when speaking, he had no problem telling me he wanted nothing more than to memorize every line of my body with his tongue. The man-child was a walking contradiction.

Yelp review:
I am admittedly a sucker for a good paradox and love it when things don’t easily fall into any one way to be classified or categorized. I love meeting someone who is difficult to understand, as it presents me with a delightful puzzle to unscramble, and the joy of exercising a muscle I love to use. In case you haven’t yet put this together, I’m absolutely fascinated by human nature, behavior, and social nuances—and my date with Brandon provided lots of opportunities to explore all of them.

Brandon invited me for dinner, and we enjoyed casual conversation. He was super cute in his intense focus and flattering with his endless questions. We talked for hours and eventually decided that we would both really like to see each other again. Overall I would give Baby Face Brandon:

4 stars ⭐️ ⭐️ ⭐️ ⭐️

What I learned about myself:  
I learned that I have been missing out by limiting myself to only dating older people or people close to my age, and not dating younger men. I have been pleasantly surprised at how much easier it was than I expected, to date outside my comfort zone. I thought for sure that I was going to need to buy the “Complete Idiot’s Guide to Understanding Millennials” in order to accomplish these 5 dates, but it turns out that all I had to do was show up with a good attitude and an open mind. Millennials are real people just like us ?. Anyway, it was so flattering how he hung on every word, asked a million questions, and seemed so genuine in his admiration for everything I shared. He was quick to compliment and praise me for things that, to me, seemed inconsequential, and it was refreshing and gratifying.

Date 35.  Country Clark

A 24-year-old party boy by night and personal trainer by day. Clark is a country boy at heart who recently moved to the city and is stumbling his way through navigating traffic circles. He is tall, broad and muscular, with light brown hair, bright blue eyes, and a permanent mischievous gleam in his eye. Though he has a man’s body, he also has the curiosity and unassuming nature of someone not yet jaded by life. His quirky sense of humor made it hard to tell if he was serious or not, causing others to pause just a little too long to comfortably still laugh.   

Yelp review:
When Clark suggested bowling, I had to chuckle a bit to myself, as that is something I would take my kids to do. I hate bowling and am absolutely awful at it, but decided when in Rome, fuck some Romans…or bowl? We actually had a fairly decent time, since there was alcohol. (Thank god for alcohol.) There were so many gaps in conversation, and he was really hard to read. By the end of the date, I realized he was just a little slow on the uptake. Good thing Clark is pretty! Overall I would give Country Clark:

2 stars  ⭐️ ⭐️

What I learned about myself:  
At this stage in the game it is really nice to be able to allow my dates to unfold as they will, knowing that each one is simply an experience that I’m sharing with another human. I’ve spent a lot of time with nice, attractive guys that I simply didn’t have any kind of chemistry with, and have gotten really comfortable with doing whatever I want with that.

At first, when I started dating, I felt like I owed the men I went out with something. If they took me on a nice date, I thought it was my responsibility to fill the silence with questions about them. If he bought me a drink, I should offer to buy him a drink a different time. If he really went to a lot of effort to think of a fun creative date idea, well, I’m sort of leading him on if I don’t really try to like him, right?

Bullshit! I don’t owe anybody anything. EVER. Once I really took a hard look at these crazy ideas and began releasing them, I started having fun, better sex, and began feeling so much better about the decisions I was making, because they were all based on what was in my own best interest.

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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.