How I Fumbled The Girl Of My Dreams, Part 1

She was easy to talk to, funny, whip smart, accomplished, and successful, yet humble and down to earth.

Three weeks ago, I downloaded a dating app. After over a year of not dating, not even trying, I craved connection, companionship, and closeness.

I uploaded a few of my favorite photos, and punched out a quick summary of who I am:

“Trail runner, skier, dog dad…

Captivated by nature, spirituality, writing, motorcycles, and chasing adventure”

I entered my age, height, education level, job title, and other relevant facts.

The next step was swiping. I was disciplined, only swiping right on the profiles of women where I felt a genuine attraction or interest.

Dating apps show you the type of women you are most likely to swipe right on.

When men complain that their apps are filled with undesirable women, such as bigger, or undesirable girls, that’s because those are the types of women they’re swiping on!

Discouraged

I’m attracted to feminine, fun loving, and physically active women, 5- 7 years younger than me (currently 38).

My ideal match is early-mid 30s, long hair, pretty, with a playful personality, and an active, outdoorsy lifestyle.

Here in Salt Lake City, Utah, where EVERY woman’s profile is photos of epic skiing, hiking, camping, or running adventures, the type I like is plentiful.

I have a lot to choose from.

My first few matches, however, weren’t really what I’m ideally looking for. They were a little older than I’m interested in, late 30s, and not as good looking as I would have liked.

Three days in, I’d only had brief, dry chats, with a handful of forgettable matches.

“…Apps don’t work…”, I rolled my eyes.

I slid my thumb over the icon to delete the app, fully intending to go back into hiding: running, lifting and working, not even thinking about dating.

Before I could remove the app from my device, something surprising happened. I was shocked to see that a tiny red notification circle had appeared.

I had a match!

Brittany

Pleasantly surprised, I clicked to check out the profile of my new love interest.

“Brittany” was mid 30s, athletic, and fit, with long, wavy dark hair, and a warm, inviting smile. Her profile was funny, punchy, and well written. She seemed intelligent, and interesting with a great sense of humor.

She divulged that she was recently divorced, busy in a professional career, dipping her toe into dating apps for the first time.

I read her profile, and fired off an amusing message about Aretha Franklin, one of the artists she said she liked.

Another shock: She responded right away!

Just five minutes later, we were deep into a light hearted discussion of 90s R&B and hip hop music from our college days.

A pretty (FIT) woman was showing a high level of interest in me: I was floored.

While her pictures looked decent, our conversations were so enjoyable; her asking questions, keeping the conversation going, and replying quickly, that I was even more drawn to her personality than her looks.

We messaged for a few more days, chatting about our jobs, hobbies, and families.

At the right moment, I moved decisively: “I would like to meet you… Would like you to get together for a quick cocktail?”

Brittany was gracious, accepting immediately, “That sounds lovely”.

We settled dates and times we were both available.

I named the place. It was a date.

First Date

As I mentioned, we’d been chatting about a mutual love of legendary diva, Aretha Franklin.

On the way home from work, I stopped at a record store, and grabbed a vinyl of an artist Brittany and I had chatted about, as a little gift. This was my first time bringing a gift to a first date.

I wanted to see how that would work, and I thought it was a nice touch.

I’ve tried the Super Stoic Masculine Frame.

It works on some women, but I’ve found that a lot of girls get bored with a guy who shows no personality, and shows no emotion, like a cold, stone statue.

Since I spent a year and a half in therapy, I am much more aware of my own emotions, and much more sensitive to the emotions of others. I’m more open, and I feel more alive. I feel more connected with people.

My initial experiences have been that women are surprised and impressed by a man that can express empathy: “That sounds really challenging. I’m sorry that happened to you…”, instead of just grunting in response when she shares her feelings.

There’s a balance. I’m still calibrating where that is.

On the evening of our date, I piloted my motorcycle downtown to the bar district. I hopped off my bike, and strode into the trendy cocktail lounge, about 20 minutes early.

When I was dating a lot, I had all my first dates at this same spot.

It’s a hipster lounge: strong drinks, dimly lit, a “cool” vibe, and stylish decor. There are comfortable leather couches arranged to face the windows that look out onto the street. It’s the perfect place to talk, people watch, and get to know someone new.

I even take sugar babies there for our first meetings.

(Reverse) Catfished

At 8PM on the dot, a petite woman in heels, tight jeans, and a flowy sleeveless top stepped into the lounge. I looked up from my drink.

When our eyes met, she smiled broadly.

“Brittany!”

I stood up and walked over to greet her with a hug. The woman before me was MUCH smaller, just 5’3, and MUCH prettier than I was expecting. Her pictures hadn’t shown off her tight, fit body, her stylish haircut, and her aura of confidence and sexiness.

Just looking at her, my heart was racing.

She gracefully sat down next to me on the leather couch where I’d been waiting for her.

“Hi! Nice to meet you!”, her soft brown eyes gleamed.

I felt hypnotized.

The woman before me was gorgeous. She had full, supple lips, long eyelashes, and clear, smooth skin.

The conversation flowed easily, just as it had in messaging online. She felt like an old friend.

I haven’t been on a traditional (non-sugar baby) date in YEARS. However, my old techniques: asking questions, holding easy eye contact, and relaxed body language, came back like riding a bicycle.

Brittany was leaning into me, scooting closer, her eyes twinkling as she smiled at me. She was engaged and interested in our conversation. I could tell that she was attracted to me, and enjoying our time together.

The Skilled Seducer

One cocktail turned into two.

Brittany talked, I mostly listened and asked questions.

On dates, a skilled seducer lets the woman do 80–90% of the talking. She talked about her work, our city, and her young daughter. I laughed, alternatively expressed empathy, surprise, and laughter at various points in her stories.

When our drinks were sipped down to ice cubes clinking in the bottom of the glass, I leaned back and gazed at Brittany’s delicate face in the soft light of the lounge.

It was about 9:30pm. We both had work in the morning. I was already feeling buzzed.

“What’s your schedule like for the evening? …Anywhere you need to be?”

Brittany shook her head, “No, I’m free all evening” she answered innocently.

“…I really don’t need another drink…”, I reasoned.

“Could you have some ice cream?”

Brittany’s eyes lit up, “Could I!”, she beamed. Her wide smile and genuine enthusiasm curled my face into a grin.

“Perfect, I know a place just a few blocks away. We can walk over.”

I settled our tab, waving off Brittany’s attempt to pay for our drinks. I held the door for her as we strolled off into the cool spring evening.

In only a sleeveless top, her bare arms looked a little chilly for the mountain air in early May. I peeled off my sweater, “Here put this on.” I offered. She blushed as she pulled the warm layer over her head.

The night was perfect for a short walk through the downtown streets. We chatted about the city, and other areas we’ve lived and traveled.

To our surprise, we had a lot in common: we had both taught English abroad, both played soccer, were avid runners, and had voracious sweet tooths.

The conversation flowed effortlessly.

Brittany was easy to talk to, funny, whip smart, accomplished, and successful, yet humble and down to earth.

On the short walk to our next destination, I felt like the star of a romance blockbuster:

Walking through the moonlit evening, a beautiful woman smiling up at me, hanging on my every word, feeling chemistry and fireworks between us every time our eyes connected.

Dessert

At the ice cream shop, we ordered scoops of frozen dessert, and sat outside at tables arranged on the sidewalk.

When the conversation lulled, I relaxed and let the tension build between us. I would gaze into her eyes softly, then look away, watching other couples stroll by, or look out onto the night sky.

After ice cream, I walked Brittany back to her car, and my motorcycle, parked on the street near the bar where we had just met.

I felt confident, calm, and self assured.

Brittany’s attraction to me was obvious; the way she leaned into me, laughed at my jokes, and the look in here eyes were signs that she liked what she was seeing.