First Dates, Lost Friends, And Lessons In Connection

By June 25, 2019 August 3rd, 2019 No Comments

I used to think dating was easy. 

What’s really to it? You meet people, you pick the ones you like and go on a date. From there, you pick the one (or few in some cases) that you still like, and you keep seeing them. 

Easy. Right? 


Only recently did I learn that there is so much more to dating than just the act itself. Anyone and everyone can go on dates – that part really is as easy as it sounds. But we aren’t in search of dates, we’re in search of connection. And connection ain’t easy. 

Finding real connection is hard. 

Real connections are few and far between. And there is so much more to it than being able to talk to someone or finding them physically attractive.

Some people can meet your standards of who the ideal person is and still, the connection isn’t there. Others come out of left field and take you for a loop because they’re not your type yet you find yourself looking at them starry-eyed and smitten. 

Sometimes, connection exists where you wish it didn’t. Those, I think, are the hardest to deal with. 

It took entering the dating world again for me to realize any of this. 

To be fair, I met my boyfriend at the ripe old age of 21. In a couple of months, we celebrate 11 years together! I was lucky to find him easily and early on so this means that real dating – the kind where you have to kiss a couple of frogs – is something I never had to go through. 

Sure, I had a couple of boyfriends and flings in high school and college but nothing I ever took too seriously so do those even count? I kind of skipped the dating line so my ideas around it were built from the outside looking in. 

My first experiences showed me how severely misguided I was. 

I had a best friend who was knee deep in the dating scene. 

I don’t mean that in a negative way at all. We were at the age where so many of us were pairing off and settling down – she wanted that too. She wanted to find her partner in life and settle like the rest of us so she took to the dating apps and put in the work to find someone. This meant lots of dates. Who could blame her, that’s how this dating thing goes. 

She’d meet someone on a dating app, chat with them for a while and feel like she’d make a good connection with him. We’d get really excited for the first dates. 

But more often than not, she’d end the date and send me the same response. “It didn’t work out. I just didn’t feel it.” 

I’d hear this from her, scoff and roll my eyes. 

I know. That’s not the kind of thing a supportive friend does and I’m mildly embarrassed to admit I reacted that way. I just wanted her to find someone and finally feel happy, genuinely happy.  I couldn’t understand how, in a single one-hour date, she was able to determine there was no spark.. no chemistry.. no connection. 

I’d ask, “Are you sure? You were so excited about him. Maybe you should go on a second or third date just to be certain.” I wanted my friend to find her match almost as badly as she wanted to. I thought that maybe she had her hopes and standards set too high – maybe she wasn’t giving some of these guys a fair chance. Surely you can’t know in one date if you like someone or not. Right? 

Wrong again. 

I had my first date with a woman after connecting on a dating app. 

If you read my blog about my relationship, then you know we’re trying out non-monogamy. When we decided to give this alternative relationship a try, I signed up for OKCupid. Apparently, in today’s dating culture, you have to have an app to meet anyone and OKCupid was the only one that allowed me to indicate I was in a non-monogamous relationship. 

It took me a few weeks to run across someone I was actually interested in. 

I didn’t really like the idea of swiping on people like they were disposable but damn was I swiping left on a shit ton. I was beginning to think I wasn’t really bi after all. Then I saw her profile. For the sake of privacy, I won’t name names here. I’ll just use pronouns. 

Obviously, her picture caught my eye. She was incredibly fit and had the world’s most perfect smile. I clicked on her profile to see more. She had pictures of her dog – ugly little thing. I had a dog that was so-ugly-he’s-cute too! 

She had pictures of her in a bikini from her fitness competitions. She was knockout gorgeous, and while I’m a tad bit shallow, I’m not that shallow so I read her profile. I don’t know if you know this about OKCupid but it allows you to have insanely long profiles – I read every word on hers. The more I read, the more I liked her. 

She was really into health and fitness. Me too. She loved furry creatures. Me too. She was very spiritual and practiced mindfulness and meditation. Me too. She was in a relationship with a man but was also dating women. Me too. She was in medical school to become a doctor. NOT me too but whoa! 

As I read about her, I started to think someone sifted through my head to create this perfect match. I swiped right on her profile but I didn’t have much hope she’d do the same on mine. 

We did match, though. 

We chatted for a week getting to know each other a bit more. The more we talked, the more we both felt like the other could be a really great match. Had I found someone outside of my primary relationship to actually connect with? 

‘Nervous’ doesn’t even begin to describe how I felt for our first date.  

It was a Thursday so I had to work. My boss and I were pretty close and he knew I was about to go on a first date. He laughed at me when he saw how nervous I was. He was shocked to see how much effort I put in to look like a mildly attractive person. I think he only ever saw me in jeans and a t-shirt with frizzy hair. 

We met at Uchi, a swanky little sushi spot in North Austin. I showed up 20 minutes early because when I’m nervous, I like to get settled into a situation before anyone else arrives. 

As I sat there, the negative self-talk set in. What if she sees me and thinks I look prettier in pictures? What if she thinks I’m boring and we have nothing to talk about? 

I was so nervous my breaths were uneven, my palms were sweaty and my racing heart felt like it was going to drop right from my chest straight out my butt. Can you blame me, though? It was my first first-date in 9 years and my first ever date with a woman. I didn’t know what the hell I was doing. 

She showed up right on time. 

She walked into the restaurant and looked around. She was in a fitting black dress with her hair down. When she looked over at me, she smiled. And in that moment, I knew, “I just didn’t feel it”. 

I’m not sure how I knew it. I don’t know how I knew, within seconds, that she just wasn’t going to be the connection I was looking for. It’s not that she wasn’t attractive. She was stunning. It’s not that she didn’t seem friendly. Her smile was warm and damn near perfect. Something about that moment just let me know that she’d be an amazing person, but not a new partner for me. 

All the nerves faded away.

Though I knew there would be no romantic connection, the date still lasted 3 hours. 

We talked about family, friends, shared our coming out stories, talked about what lead us on our spiritual path and why we’d want this kind of relationship. She was really great. Smart, funny, pretty, into fitness. She was everything I could want. And yet, she wasn’t. 

I felt awful too. She told me she really liked me, hoped to see me again and Invited herself to an outing with my friends which she acknowledged was presumptuous of her. I cowardly mimicked her feelings though they weren’t true for me. I said that I’d be open to seeing her again. I was too scared to flat out say that I wasn’t feeling it. I also wanted really bad to “feel it”–  to feel something that made me think a real connection would come of this. 

I thought about ending the night by walking her to her car and kissing her.. 

Maybe that would ignite a spark or show me that there was a possibility of a connection. But I just couldn’t bring myself to do that. After a lifetime of going against myself, I didn’t want to do that again. Instead, I gave her a hug, thanked her for a good first date and said I’d reach out.

I went to my car and sat there for a while as I stewed in what had just happened. I was kind of sad and disappointed, to be honest. Not in her or the date. I was disappointed in myself. 

I had waited all this time to finally be out, to live openly as who I always felt I was. I was on my first date with someone who, on paper, seemed perfect. She checked off all the things on my mental checklist but I just didn’t feel it. 

Here I was, not straight enough to live a fully heteronormative life, not gay enough to say I’m a lesbian and now, I’m not even doing bisexual very well. Turns out my identity crisis wasn’t over yet. 

I went home to my boyfriend, to the arms that felt like home. 

I told him about everything. “You spent 3 hours with her but in the first 30 seconds you knew there was nothing there?” He didn’t get it. Just like I didn’t get it before with my best friend. But I got it now.. 

It was an interesting first experience and while I felt a little confused by it, I was finally out and living my life the way I had always wanted to so I couldn’t let it stop me. 

I shook off the disappointment and decided to try again. 

It took a couple of months before I made a connection with someone else.

I got a long message on OKC one day from a girl that was pretty but not someone I think I would have typically been drawn to. While her message could have been a copy and paste template, it was hilarious and sounded like something I would have sent. “First off, I don’t know how to do this.” Girl, preach.  🙌

We seemed to really connect. She was easy to chat with and had a good sense of humor. She was traveling so we spent a month or so texting before we met. I could have totally been getting catfished and wouldn’t have known. 

Eventually, we made plans for a first date. 

It was the beginning of December and cold that day. I put in about half the amount of effort getting ready for that first date as I did for the previous one. After my first first-date, I didn’t have high hopes. Damn, I get jaded fast. 

I wasn’t really that nervous but I still showed up to the Driskill first. I sat reading a book as I waited for her. I tired and ready to go home. Then I heard a “Hey girl” to my right and saw her. Her smile lit up the room and she herself seemed vibrant and bubbly. I even liked her voice and the way she greeted me like we had known each other for a while.

I liked her and it took .5 seconds to realize it. 

The nerves rushed in.

We spent a few hours talking. Or rather, she was talking and I was stumbling all over my words. I was certain I sounded like a babbling idiot and she’d probably want to end the date soon. At about 9 I asked if she was ready to go. She said yes but asked if I wanted to go someplace else. I was shocked that she’d want to spend any more time with me than she already had to. 

We went to a rooftop bar and sat by a fire for the rest of the night. 

That first date lasted 5 and a half hours. At one point she called me out. “You’re smitten over me. I can tell.”  I was. 

At 11 I decided to head home. Out of respect for my boyfriend, I didn’t want to be out past midnight so I walked her to her uber. I thanked her for a good night, we hugged goodbye and she asked if she could kiss me. 

Things were really fun and exciting for a few months. 

It was fun to hang out with and get to know this new person. It was also really nice to get to know this new me. I’d still get really uncomfortable being close to her in public settings, but I was learning to let that go. The fear of other people’s judgment faded a little, and the tolerance of other people gawking at us increased a little too. I felt like I was growing more comfortable in my own skin.

My boyfriend was really happy for me but he was also a little nervous at the idea of meeting her one day. We all were – it was new terrain for all of us.

My best friend was supportive but concerned. She was worried this new girl would steal me away. I assured her that could never happen.

My new world was taking shape nicely….

But then, life got bumpy. 

I’d been struggling with my job for a few months by that point. I was totally unsure of what I wanted to do with my life but building out Salesforce wasn’t it. I grew increasingly unhappy there. 

Later, my relationship with my best friend fell apart. 

It wasn’t big and ugly. It was subtle and surprising.

Losing her hurt me more than I let on. I was confused, angry and in quite a bit of pain – it took nearly all of my energy to put a smile on my face and accept the fact that she chose to walk out of my life. 

My relationship with my boyfriend, though, that was better and stronger than ever. Thank goodness because I leaned on him heavily during that time. 

Between work, my relationship and losing my best friend, I was depleted. 

What little energy and emotional capacity I had left needed to go to my boyfriend. It didn’t seem fair to try to hold on to this second relationship when it was starting to feel so wrong. 

Over text one day, I told her I couldn’t see her anymore. I know that sounds shitty and maybe even cowardly, but I didn’t have it in me to cut things off in person. I also wanted it to be done as soon as possible. 

She was really receptive of it, actually. And that was the end of that. 

Once the dust settled, I went on a few more dates. 

Each time, I just didn’t feel it. I’d either become strictly friends with that person or I’d never talk to them again. I started to realize that there wasn’t going to be anyone that would make me feel like I was connected to them again – not anytime soon at least. 

I was going on dates because I was trying to fill a void. 

None of these dates, not even the woman I dated for a few months, was the person I wanted them to be. 

My heart was set on two people. One I had in my life already – our relationship was strong and rewarding. The other had just walked out of my life and I had to learn to let her go. The connections I had were the connections I wanted and no amount of dating new people were going to fill those spaces in my heart. 

With the realization that dating is more than just seeing ppl, liking them and seeing them over again, I deleted the app off my phone. I disabled my account and decided to just focus on me, my boyfriend, my work and my writing for a while. 

And here we are. 

I learned a lot through dating again.

It made me realize how off the mark I was when I thought about the subject. It made me eat the words I had once told my best friend. 

Dating is easy but that’s not the part in question here. Dating and making a connection on the other hand – now that is hard. 

Sometimes you can want to make a connection with someone so badly because they mark off everything on your proverbial checklist yet, the connection just isn’t there. 

Some connections build over time. They start out great and grow to be something more wonderful than you could have ever imagined. Those are my favorite!

And then there are other connections – ones you wish didn’t exist. They only complicate things and make the waters murky. You’d like to erase it but you can’t so you settle for pretending like nothing is there at all. 

You can’t force a connection and you can’t delete it either. It exists or it doesn’t. More often than not, your heart knows this before you even have time to think about it. 

Yes, connection is complicated.

But I swear, it’s also really beautiful. There is no amount of pain or sadness, disappointment or wishful thinking that will make me change my mind about that. I have enjoyed every single up and down I’ve experienced while exploring this subject and I will continue to do so.  

I hope you’re also getting the chance to explore this subject more. I hope the connections you have are rewarding, or at the very least, teaching you lessons. I hope you see the beauty in the pain, miracles in love and excitement for all that exists in your life! 

Here’s to good first dates and creating connections!

Like this story? Let me know! Curious to know more? Reach out! Have a story of your own? Share it with me! None of these apply to you? That’s OK, still love you!


Author roryruedas

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