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  • Ryan and Skylar

December Dates #3


Key Takeaways: It’s unfair to compare. And DO NOT ask questions about family right at the beginning


Name: Macaulay: they are a former child actor. Like Macaulay Culkin from The Pagemaster (and other cinematic classics)

Length of date: 1 1/2 hours

How the date was obtained: Grindr

Where: The neighborhood surrounding Barnes and Noble in Sherman Oaks

In the words of every Love Island-er: we had good chat. Through the phone, at least. Now is the time when I should explain that I do not consider myself gay. “Gay” can be a fairly restrictive term. I use it mostly for the benefit of straight people understanding the broad strokes of who I fall in love with. I have not been in love with a woman and I have not been sexually attracted to a woman, but I would be totally fine if one day that happened. I have, however, been very into non-binary and gender-fluid people. These are terms I could take the time to define, but they are completely Google-able and I feel I’m already in the weeds of a Gender 101 course. Suffice it to say, there’s a lot of middle ground when it comes to male and female. This week’s date was with someone non-binary. This was not the first time I’ve gone on a date with a nonbinary person and I doubt it will be the last. I will be using the pronouns they/them/their to describe the date. We texted a LOT leading up to our meeting. It was the best kind of texting, with constant jokes about books. We decided our first meeting should be walking around a Barnes and Noble. So, we agreed to meet at the open one near us. One problem: when we arrived, the Barnes and Noble was not actually open. We agreed to just walk around the neighborhood. Macaulay was incredibly attractive and very sweet. We grabbed some coffee and disappeared into a beautiful suburban neighborhood nearby. Pretty quickly we got into some tough topics. It felt like we stumbled into a sadness minefield with heavy metal boots. Both of us asked all the wrong questions. It was clear we appreciated each other, but we just couldn’t find the right questions to ask. After some truly Herculean effort from both of us, we found a few safe topics. They talked about the type of house they would build with a little money (mine is a woodland log cabin, theirs is modern and upscale). We found a fun rhythm, tossing jokes back and forth. The only problem is that the texting was so good, the conversation could only be a little bit of a let-down. It was still fun, though, and we made quite a few laps around the neighborhood. My date with a friend from the week prior was SO natural and fun, that I found myself wishing I was hanging out with him. And my recent ex is SUCH a deep thinker and feeler, that I found myself comparing Macaulay’s perspective to his. It wasn’t fair to them, but I couldn’t help but compare time with Macaulay to two people I‘ve already gotten to know. It was clear Macaulay wanted to hang out again, but I knew it wouldn’t lead that far because I was too hung up on other people. I felt bad, but I sorta knew goodbye was probably final.

Overall Experience:


The future for us… We texted a bit, but it ultimately fizzled. Macaulay’s so smart, cute, and sweet that I feel like a jerk for where my brain was on the date

Next Week: I’ll let you know when I figure it out.


Key Takeaways: Our differences are what make us interesting to each other.


Name: Jake because he's an insurance agent, although not from State Farm. Thankfully he did not show up wearing khakis.

Length of date: 1 hour 45 minutes

How the date was obtained: Bumble

Where: Bon Bon Tea House (the Canoga Park location), my home away from home, my true love

Jake and I were pretty much on the same page from the moment we started talking. Both trying to find our feet in a solid career path, both looking to get out of our dating comfort zones, and, most importantly, both animal lovers. Texting him was super easy, so I had no reservations about our in-person conversation being just as natural. Plus, he's a quick responder, which is good since nothing makes me lose motivation quite like consistent 4 hours later responses. We even arrived at Bon Bon at the same time. He sped through the yellow light that I stopped at, but that is pretty much where our differences ended. I don't think we disagreed or had differing opinions on a single thing we talked about. It was like we already knew each other.

Theoretically, we actually could have already met since his early childhood was spent in my hometown of Las Vegas. After a good amount of time spent sifting through every school, soccer field, and children's birthday party location we had ever been to, we decided we probably had never met each other. Although my sister's best friend did work at the same Pei Wei as his cousin so . . . who really knows. But in all seriousness, we were similar. Very similar.

In a way, our many similarities were comforting, and it was nice to take nostalgic trip through my childhood memories. Our shared social and religious views, as well as our general views on life, made me feel like we could be very content with each other. Ultimately, it felt like catching up with a friend that I probably won't see for another 10 years.

Overall Experience:


The future for us… As much as I genuinely connected with Jake, I don't feel particularly inspired to plan a time to see him again. It's difficult to explain, but I just felt that maybe something was missing, although that is a big judgment for only two hours of time. That doesn't mean I wouldn't find this elusive "something" on a second date though, so I'm definitely open to it.

Next Week: I don't have a date lined up yet, but I am driving home for Christmas. If there is anyone out there who has carried a torch for me since my Las Vegas days, reach out. Please. Maybe I can go on a date with someone I actually did grow up with!


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