10 Lessons Learned in a Year of Dating

I’m 31 and since I was 18, I’ve been in 3 relationships lasting 4 years, 7 months, and 6 years. Which means I never did a lot of casual dating and definitely not in the age of Social Media and dating apps. The two big relationships I had were with men who were extremely wrong for me. I naively believed if I loved them hard enough, I could make it work. All of the these facts culminated to one big challenge, I have a lot to learn regarding dating.

This year, I treated dating as exposure therapy with a “come what may” attitude. I signed up for online dating and accepted dates if the men came across as decent people. What resulted was first dates with 33 men this year. About a third of these men were met organically at events and through friends and in line waiting for tacos, and the rest were from online dating sites and dating apps. My goal was not only to possibly make a lasting connection with someone but also to learn all the things most people learn in their 20s that I didn’t learn. I want to learn what I want, what I need, what I don’t want, what I don’t need.

The whole experience has been fun, scary, exciting, eye-opening, humorous, humbling and surreal. I mean, I had my first first kiss in over six years and then a few more. I trespassed on private property on a second date. I tried dating a friend. I went out with engineers, writers, doctors, comedians, and a puppet maker. I ran into someone I was supposed to have a first date with the next day while giving my number to someone else. Someone asked me out while I was waiting for a date to arrive. I dated younger and older, poorer and richer. I hurt a few people’s feelings and had mine hurt. The range of experience in just a year was wide and varied.

Of course I took detailed notes to try make sense of it all and discover patterns. And here are just ten of the lessons learned.

  1. I learned meeting strangers or acquaintances over coffee or dinner gets easier and easier the more you do it. The first few first dates I’ve gone on, I’d fret about what I’m wearing and was sweaty with nerves up to the point of meeting them. In time, I found my prep before a date is now just reading a book or watching a show right before having to leave.
  2. I learned that the advantage of meeting people already vetted by your friends is you feel safe enough to let them pick you up for a date. Being picked up for a date adds a bit of magic to the date.
  3. I learned that I’m picky and that though I’m cautious and skittish, I’m not completely closed off like I feared. Of the 33 men, I was willing to pursue the possibility of a future with two of them. I had a huge crush on one the first quarter of the year and developed feelings for a second towards the end of the year. I was brave and I let someone in! I’m still standing!
  4. I learned that I’m scared of getting what I want and this manifests itself as nitpicking and making up superficial deal breakers. I have to be aware of any self sabotaging instincts and behaviors.
  5. I learned that I need a mix of intellectual conversation and play time. I want someone whom I can have long meandering conversations with that keep me engaged and someone who is willing to dance like penguins with me in the parking lot of a bowling alley. If you’re not willing to be stupid with me, it sets off alarm bells.
  6. I always try to treat people with care, but dating has really brought into light that though no one likes the sting of rejection, being the person rejecting is hard too. And I had to learn to carefully, honestly, and compassionately choose words when letting someone down. I learned that even if it’s easier to ignore text messages, sometimes there has been enough time spent together to make that uncomfortable conversation kind and needed.
  7. I learn that the people you casually date can also just become friends. I was under the impression that when you’re done, you’re done. I managed to keep some of the men I went on a few dates with as friends. This also hinged on the previous lesson. These friendships were made possible because I didn’t just disappear and forced myself to have those uncomfortable conversations.
  8. I learned being out and open can lead to happy accidents. I had a spontaneous first date with a stranger while reading a book in a coffee shop. He was brave and approached me and I didn’t have anywhere else to be and he seemed normal enough. We ended up having a conversation over coffee for over an hour.

  9. I learned my primary love language is definitely words. You can be attentive and give me gifts and do acts of services, and though I’m very appreciative of these actions, I don’t hear your message behind these kind acts unless they come with words. I very much need to hear or read actual words to register someone’s feelings towards me.
  10. I learned that though my goal is to find someone I can build a life with, I’m comfortable with the idea of living my life without a romantic partner. This feels like power. I can hold out for someone who is the best fit for me and don’t have to settle. I don’t have to settle because if I end up living my life alone, I’m confident I can make it a beautiful and happy one with my pursuits of adventure and with my friendships.

With the dawn of a new year looming, I’ve been reflecting on 2014. It has been a hard and amazing year and dating was a big life change in 2014. I’m curious to see what lessons in dating I’ll experience in the new year and remain hopeful that maybe 2015 is the charmed year when it comes to romance.


Tell me about some of your lessons learned while dating!

November On & Off Instagram

I mentioned October was a force to be reckoned with. It was extremely hard for me emotionally and then there was one final surprise punch the very first few hours of November while I was on a trip to New York. I spent the rest of the month regaining my footing and licking my wounds. Luckily November tends to be great for my soul because of the reunions that start happening around Thanksgiving.

There’s a lie I tell myself often. That I’m unlucky in love but very lucky with friendship. The lie is I’m not unlucky in love and I should stop telling myself that because I will manifest it. When things fall apart for me romantically, as it kind of did with a new person in New York, I am always humbly moved by the depth of love and friendship my support system instantly extends me. Hours after upsetting news even in New York, I was able to spend time with close friends who live there. They offered me warm shelter and a trip to famed bookstore, The Strand, and bowls of noodles two days in a row. How lucky am I to find that kind of comfort and love when I’m in New York? One of my friends even took me to New Jersey so I can cross another state in my 50 states quest, bringing this year’s total to 5 new states. I was only shooting for 4 new states this year!

The week I got back from the trip to New York, I packed up my life in three days and moved from North Austin to South Austin, which cut down my work commute from 2 hours a day to 30 minutes a day. I have a new roommate and marveled that last year I was packing up my life and sobbed the whole way through. In just one year’s time, I moved again and though I wasn’t sobbing, I wept over another man. It amazed me how far one year took me. If you told me last year that in an exactly a year I’ll be crying over someone else, I’d dismiss your general credibility.

I went to the second reading party of my life (hosted by the same person of the first reading party). It’s one of my favorite kinds of parties. I had many coffee dates with friends and was reunited with two of my best friends in Houston for our Annual Day of Magic. This year’s Day of Magic included swinging on swings with children in a park, admiring a field of light, and sneaking up to a rooftop of a skyscraper to take photos. I am newly resolved to hang out on the rooftops of skyscrapers at night more often in 2015. It lit a fire in me!

Not depicted on Instagram, a comped ride to and from the airport from Blacklane. I wasn’t otherwise compensated for trying them out. It was such a welcomed sight to see the driver greeting us with a sign, “Monkeys in Austin.” When you order luxury rides from Blacklane you can customize the greeting sign and it tickled me to surprise my friends with our self-ascribed group nickname of “monkeys.” Also not depicted on Instagram was me fulfilling a bucket list item by riding a mechanical bull. 2014 has been a successful bucket list year for me!

Friend

Moving

Reading Party

Kerbey

Whole Hog

Bobby

Cortados

Swing, Swing

10

Thanksgiving

Go Away

Street Art

Field of Light

Houston Skyscrapers

You can follow me on Instagram @curiousnotions.


Question: What were your best moments from November?

Making Do And Feeling Rich

I’m drinking warm tea from the very first mug I bought myself. I got it from a dollar store and it has a photo of a Golden Retriever wearing glasses. I remember feeling that the mug represented adulthood. I was finally living in an apartment, not my parents’ home that was already stocked with drinking ware or a dorm room where there was no room for dishes. It has survived over 10 moves and now resides in the community cabinet at my workplace. I share it with my coworkers and today it sits on my desk and it makes me smile that it has been a companion to me as I wade deeper into the trenches of adulthood for over a decade. The CEO has told me it’s one of his favorite mugs.

The first couch I owned was originally my parents’. My boyfriend in college tackled me onto the couch and broke one of the legs. It survived two years in my living room with a stack of textbooks as stand-in for the missing leg. It was my couch the first time I lived on my own sans roommates. It was the place I moped and watched a ton of movies. It was the couch I had when I experienced my first heartbreak by the same boyfriend who helped me break it. It was the first couch my younger brother ever experienced. I have photos of myself kissing my new baby brother on that couch. It was a piece of my childhood offering somewhere to rest when I was on my own for the first time.

Today, I’m newly moved into an apartment and we are without a couch. I had sold most of my furniture when I moved in with the ex. Cohabitation with lovers can be very bad for furniture. Living without a couch has made me wistful for that three-legged ugly couch.

I know years from now I will remember coming home to my current apartment. Seeing my friend and new roommate on the floor. Both of us laying on the hardwood floors and exhaling from a long work day. Earlier this week the pizza delivery guy knocked and she got up and I remained motionless, flat on my back in the middle of the floor. The pizza guy peered over Ashley’s shoulder and laughed. “Is she okay?” Laughter. “We just moved.” I will remember our first night together sitting on the floor and watching Youtube videos of romantic proposals. Her eating candy corn, me eating cereal. “Ready to watch other people be happy?”

When we look back at the moments we thought we were just merely making do with what we have, we’ll learn with the rosy tint of hindsight, that we were in fact very rich.

October On & Off Instagram

October was a force to be reckoned with. I am someone who pays attention to anniversaries, even the sad and heartbreaking ones. October contained the one year anniversaries of the deaths of two friends and the anniversary of the breakup of a six year relationship. The first week of October was hard. I nearly missed the anniversary of one of my friends’ passing. Luckily Treavor so sweetly sent me flowers in her memory and reminded me. I nearly missed it because I had a sick puppy and it hit me how alone I am essentially. The last time Bob the Dog was sick, I had a work-from-home boyfriend who could let him out every hour. I went home three times in one day while living an hour north from work to clean up after Bob. I threw myself pity parties and then quickly had to switch gears to celebrate the wedding of one of my close friends in Houston.

I went to Houston twice in October. The second time was to have a weekend with Oprah with my best friend. I’m still riding the motivational wave of Oprah’s The Life You Want Tour. In fact, her opening speech alluded to stars and the Milky Way and I paid homage by dressing up as the Milky Way for Halloween in New York City.

This month I convinced my mom to have a gazing at the world date with me every time I go to Houston.

I flirted with Neal Patrick Harris and bought a signed copy of his new book, Choose Your Own Autobiography. He is so handsome!

My crazy month ended in New York City. I went with a big group of friends and though I mentioned the second half of the trip crushed my spirit, I spent the last day and minutes of October having truly an awesome time in a city I love with great people.

Not depicted on Instagram were a lot of tears.

night in

GeekyHooker

Players

Momma

Pizza

Oprah!

Reading at Oprah

Neal Patrick Harris

Austin

Seafood Risotto

NYC

NYC

Halloween

You can follow me on Instagram @curiousnotions.

Not Faking It Until I Make It

I am back from my New York City trip. It was my sixth visit and also my hardest. Just two days into the trip I experienced a falling out with a friend. I felt blind-sighted, disillusioned, angry, heartbroken. I had previously felt so certain that this person was the safest person with whom to have a friendship. He was just that nice and that good. Unsure about what kind of relationship I wanted with this person, I cried and leaned on a few of my other friends. Sometimes clarity comes with well-intentioned advice that feels wrong. A couple of my friends suggested I “fake it till I make it.” They urged me to just act as if I am fine and not give the person the satisfaction of knowing he had that kind of power. “That would really show him!”

I have a long history of swallowing grievances for the sake of pride and winning. My parents raised me on many of their own mantras, one of which was, “Don’t cry about people who aren’t crying about you.” I was raised by parents who were also taught to never let people see you vulnerable. It wasn’t until a few years ago that I realized in learning to silently and secretly bear trespasses, it kept the perpetrators in my life for much longer than was healthy. A defense mechanism that developed as a byproduct was very high tolerance for pain. Pain is how we know when something isn’t working or isn’t healthy. So consequently, I also developed high tolerance for people who were bad for me.

It wasn’t till my late twenties that I learned the value of pain. Like a lot of people, I’m hedonistic by nature and I lean on the pursuit of pleasure as my most sought out cure for pain. Sweep icky feeling under the rug and go on a trip or eat a whole half gallon of ice cream! But pain is good. Pain tells you when something isn’t working.

Another thing my loving but humanly misguided parents taught me that I had to unlearn was not using my words. They commanded me to always hold my head high and never let anyone suspect that they hurt me. With a lot of practice, I got to be very good at silently suffering until I felt numb. Which enabled a lot of mistreatment. Which toughened me up for more ensuing pain from these toxic people because they learned they can do anything and I wouldn’t speak up.

Terrible cycle.

So when my friends suggested I fake it till I make it with this person who made me crumble on what was supposed to be a fun trip, I felt a very clear resolution rise from my stomach and into my heart.

I am no longer pretending with people who hurt me that they didn’t hurt me.

In deciding that, every superficial conversation initiated by this person felt like an uncomfortable game of charades. I took two more days to steel myself to speak up and when I did, it felt so good to be honest. Not only to him but also to myself. I felt strong. Powerful.

Who would have thought that in admitting feelings of hurt, you can actually feel strong and powerful?

September On & Off Instagram

As I mentioned in my August Instagram recap, I was in Greece the last few days of August and first week of September. In September I was in Santorini and then I ended the trip with a couple of days in Athens. It was surreal to finally cross off a couple of things on my bucket list that I’ve had on my list for almost two decades.

I went to my second Chris Guillebeau book signing with Anita and bought Happiness of Pursuit. Also with Anita, I attended a party where Ethan Hawke was an honored guest at the Arlyn Music Studio and a Texas politics festival where we sat a few feet away from Wendy Davis, candidate for Texas governor.

I attended a beautiful wedding of college friends and celebrated the birthday of my future roommate and the third year adoption anniversary of Bob the dog. One of my closest friends who lives in Miami came and we shared our usual Brazilian meal. We only spent two hours together and I miss her so much already.

Not depicted on Instagram was me spontaneously taking the stage of a comedy show for 90 seconds and dishing out unoriginal jokes and having the crowd and stage full of professional comedians in stitches. I’ve been secretly dreaming of delving into stand-up comedy and that experience gave me a fun glimpse into that dream. I also had drinks with three friends and somehow while buzzed, we hatched a plan to go to New York City for Halloween. A week later, still compelled when sober, we booked our tickets. Since then, our trip of four friends have grown to a seven people group trip!

Parthenon

Gyros

Santorini

Austin Way Launch PartyLove

Bob the Dog

Wendy Davis
sept4

Happiness of Pursuit

Ashley's birthday

Magical Garden

Sao Paulo

You can follow me on Instagram @curiousnotions.


Question: Tell me about your September?

Romantic Santorini

Last month I finally experienced something that has been on my life list since high school, and that is to visit Greece. MJ, Anita, and I spent over a week island hopping around Greece and my favorite island visited was Santorini. I always learn about myself when I travel to new places. In Greece, I learned I can plan a trip around beaches. I assumed I was someone who prefers the metropolitan and urban travel destinations. I thought I’d always pick the Lourve or the Met over sunbathing and reading in sand. The rush of navigating a subway system over wading into a deep blue sea. Greece, and more specifically, Santorini seduced me with its pink and orange sunsets and blue horizons.

Like my trip to the Grand Canyon in March, Greece taught me the beauty and luxury of slowing down. To let moments lap at you. We spent a lot of our time leisurely moving from beach to cafe with a beach view to another restaurant with an amazing view. The beautiful views were so abundant, it felt like an embarrassment of riches. I read four books on this trip and ate my weight in mussels and creamy carbonara. I also skinny-dipped for the first time and was exhilarated I crossed this off my list in the Aegean Sea instead of an apartment complex pool back at home.

I started 2014 in the wake of a break-up of a six-year relationship and since then have been on this journey of self-discovery and rediscovery. I’m so thankful Santorini and other islands of Greece were part of this year’s story.

Santorini

Santorini

Santorini

Santorini

Santorini

Santorini7

Santorini

Santorini

Read about a lunch I had in Mykonos, Greece on my food blog.

August On & Off Instagram

In August, I had a photo-taking meet up with a friend. We chased the light around downtown Austin and snapped photos to hone and practice our skill. It was during this endeavor that I met a unicorn.

I met up with a couple of guy friends. The three of us sat on a balcony, drinking sake and eating chocolate and shared painful stories, punctuated with humorous anecdotes that relieved us of the ache. After I peeled myself from the refuge of the balcony floor, I received a Snapchat photo from another friend captioned “boys’ night”. I responded with a group selfie with the same caption. We made an unlikely trio and our night of being vulnerable with each other is not typical for us. So much so that I doubt we’ll ever do it again and yet this night was the most comforting night I had in August.

August ended with my leaving for my big trip of the year. Anita, MJ, and I left on the 28th to fly to Athens. By the end of August we had started island hopping in Greece. We sunbathed in Mykonos and walked around Santorini. I can’t wait to show you the rest of the photos from Greece in the September recap.

Not depicted on Instagram, I went on a couple of dates with someone I’ve been harboring unrequited feelings for for months. It hasn’t progressed much after that but it remains a highlight of the month. As painful as it is to not see reciprocation, being around him makes me smile. Oh the angst!

Watermelon Popsicles  Unicorn

Boy's Night

Downtown Austin

Odd Duck Brunch

Pay it Forward with Daniel Curtis

Mykonos Street Artist

Ferry to Santorini

Santorini

Mykonos

Santorini

Santorini

You can follow me on Instagram @curiousnotions.

Experimenting with Being Naked

I’ve started dating this year and I’ve been careful with doling out aspects of my personality and history. It’s safer and feels more responsible. I read in one of Brene Brown’s books about how the difference between vulnerability and over-sharing is that one is an act of trust, incrementally arrived to, whereas over-sharing is an act of desperation. Alongside dating, I’ve also started challenging myself with fears. I did it as a 30 Day project in December and called it Fear Factor December. I challenged myself to face a fear every day that month. The spirit of this project has resonated even after December and I’ve found myself being intrigued by my fears and toeing more lines, from dating to rappelling down 38 stories.

A reoccurring fear I keep bumping up against is being naked and exposed and authentic, or being seen for who I am. There’s so much risk in being yourself. Not only is there the general fear of rejection that I think is part of the human condition, but also the fear of being misinterpreted. Someone not accepting me for who I am is scary but if what if they reject me on a misinterpretation? What if they get me all wrong?

The act of letting myself be seen is also an act of consciously letting go. I surrender to the illusion of control. I can never fully protect myself from rejection. Even if I am careful with what part of me I reveal and on what timeline I do it, there is never going to be a guarantee on not being hurt.

So I’ve been literally and metaphorically experimenting with exposing myself. I am self-conscious about a surgical scar that runs down my back. Because of my insecurity, I typically avoid being seen in my bathing suit or tying my hair up when I’m wearing a strapless sundress. I’ve started to go to the pool when it’s nearly deserted and tying my hair up. I force myself to sit there and enjoy my reading until I am not even thinking about how I’m feeling naked and flawed. I went on a date with someone who I consider first a friend, which is terrifying. There is no hiding who I am when we’ve been friends for a while now. Yet there I am standing, hoping that the flawed parts of my personality he is already privy to doesn’t scare him away from me romantically.

As uncomfortable as it is to stand in the light, the reason why I push to overcome this fear is the payout can be so great. How freeing will it be bask in sunlight and not worry about my physical flaws being judged? How deep a love can I experience if I don’t curate what I project? If I can simply be and still be loved for it?

Yes, I must keep toeing this line.

Conversation with Dad

He held me by my shoulders and looked me in the eye. “Baby.”

I braced for impact. He calls me baby to lace his hard words with sweetness.

“You need to slow down. If you don’t slow down, no one can catch you and no one can fall in love with you.”