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  • Ryan and Skylar

December Dates #1

If you missed Ryan and Skylar's introductions, you can read them HERE! Find out about Ryan's budding stand-up comedy career and what Skylar's looking for!


Key Takeaways: Nazis are the reason meth is such a big problem & I need to do some soul searching


Name: Owen, because his voice was like Melissa Villasenor doing an Owen Wilson impersonation on Saturday Night Live.

Length of date: 1 hour and 48 minutes

How the date was obtained: Grindr

Where: The Grove and Pan Pacific Park at Night

I'll admit, I was surprised when Owen asked me on a date. We'd barely chatted. I knew next to nothing about him except he had a nice 'stache and some great hiking photos (hiking photos do it for me--I'm the whole demographic). In fact, we hadn't even exchanged numbers when he asked if I wanted to get together for coffee in the park. When the time came to meet, my head wasn't in the game. I'd just had a short conversation with my ex, I'd worked eleven hours and this was about to be my first date with anyone new in over a year. But, I was determined to make it happen. I downed a Celsius Energy and listened to some Missy Elliot to get my mood up.

When I first saw Owen, it was a pleasant surprise. He was even cuter in person than those sexy, sexy shirt-on hike pics would have suggested. But ohh boy could he talk. At first I thought he was nervous, but eventually, I realized he's just like that. He told me about friends from his high school days and somehow that got him to the intersection between Nazis and meth (to be fair, I googled this later and it is crazy interesting). I mostly just said "yeah" and "cool." We walked for about an hour, going from the Grove and into Pan Pacific Park. I told him a few things about myself when he'd take a long breath. We weren't clicking.

Somehow, someway, we found a moment of silence. He mentioned being incredibly lonely during Covid. He'd lost touch with his people. This was the first interaction he'd had in weeks outside of work. This was a totally different Owen. He was just starved for people caring about him. I told him a few more vulnerable things about myself and coming out and he returned the favor. The conversation was lively, fun, and honest. Too honest. Because then I told him that I wasn't always a big fan of Grindr. He asked me why and I told him that I was not a fan of the way people just expect sex immediately. It felt like a transaction. And he told me that was why he'd asked me to meet up--he was interested mainly in the transaction but wanted to be sure I wasn't a psycho.

So I should have vetted that. Whoops.

The good news is we had talked long enough that we'd struck up a weird sorta-friendship. We chatted for another half-hour, enjoying each other's company. He gave me his number and told me if I decided to be "transactional" to hit him up.

I said "maybe" but most likely meant "no." And we've texted jokes back and forth a couple of times since.

Overall Experience:


The future for us… Owen and I most definitely aren't gonna "date." I like him as a person, though. Crazy enough, I could see us being friends who make transactions if that's what I was wanting.

Next Week: I take a cutie to the grocery store at 11pm and we call it romance (because it kinda might be).


Key Takeaways: I respect a man bold enough to order my boba for me


Name: Jack because "all work and no play makes Jack a great LinkedIn connection" (that's the saying, right?)

Length of date: 1.5 hrs

How the date was obtained: I asked him out over Hinge because he correctly identified the best boba shop in LA. This quality is definitely among the top three things I am looking for. (Not seriously but . . . kind of).

Where: Bon Bon Tea House off of Reseda

Full disclosure: I definitely have a lot of dating anxiety and I knew I was going to have to do something drastic to put my mind at ease before going on this first date. “Something drastic” ended up being obsessively cleaning my room and listening to the Mama Mia soundtrack. I’m not quite sure why, but this combo really settled me. I swear if I continue going on dates, I’m going to be able to eat off my floor! Unfortunately, the 25-minute drive was just enough time to get me back in my own head, and when I got to Bon Bon Tea House, I was strongly considering not getting out of my car and driving right back to the comforts of my home. And by strongly considering, I mean I literally had a “can’t make it” message locked, loaded, and ready go. I was going to send it, change my name, and then probably flee the country. But instead, I turned off my phone, took a deep breath, and reminded myself not to get in my own way.

I sure was glad I didn’t bail because Jack had already ordered drinks for both of us. Typically, I feel like ordering for your date is a VERY bold move. However, we had previously talked about how my friends and I liked guessing the flavors of surprise drinks. I was right on time, so Jack must’ve gotten there extra early for this surprise. It was super sweet and thoughtful! Also, he chose thai tea, so I immediately knew he was a man of refined taste.

Now, I hadn’t actually talked to Jack that much prior to suggesting we meet up. I had already wasted time talking to a guy that really wanted to drive in my car with me and by the time I got around to talking to Jack, I honestly just wanted to set up a date. We had one nice, albeit short, conversation before I suggested we talk more in person. At least that meant there were practically unlimited topics for conversation! I’d known he was coming to our date from work so my first question was about his day. He’s in the medical field and also taking some classes in hopes of one day becoming a physician. Exciting! Maybe he would have some interesting stories.

Tragically, his job and future as a physician became the only thing Jack seemed to want to talk about. He gave me his entire education and professional history and then asked me about my “work experience.” Yes, that was the phrasing he used. I quickly started to feel like I was in an interview. I half expected him to ask me about my greatest strength and weakness. Once we started down this path it was difficult to move to a different vein of conversation. Get it? Because he’s in the medical field? (That one’s for you, Jack). I tried a couple times to switch the conversation away from work, but his response was basically that he didn’t really have much time for anything else. I do admire that Jack seems very driven and I'm happy that he has so much passion for his career path, but after nearly an hour on the same topic, I was ready to go. I definitely love my job too, but at a certain point, I felt like I was only getting to know Jack as an employee and not so much as a person.

Overall Experience:


The future for us… While my date with Jack was generally pleasant, it did have a weirdly professional overtone, and I don't think either of us really felt any kind of romantic spark. Maybe if I ever decide to switch over to human medicine I will network with him!

Next Week: Did you know that sea turtles eat jellyfish to get high? And that's why the turtles in Finding Nemo are total stoners! Neither did I before matching with a guy who is just full of fun animal facts. We have scheduled a video date and I'm definitely looking forward to some lighthearted, goofy conversation. This will be my first video date so let's all hope that my screen doesn't freeze and expose any extra chins. Fingers crossed!


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