top of page
  • Christine and Ryan

October: Dates #2

RYAN'S DATE #2 (+ #3)

Key Takaways: If you shoot your shot enough, you’ll accidentally schedule two dates for the same night


Name: Date #1 of the night - 50 Cent, because I felt like I was in the song “21 Questions”. Date #2 of the night - Gabriella, because her favorite movie is High School Musical

Length of Date: 50 Cent - 1.5 hours, Gabriella - 3.5 hours

How the date was obtained: 50 Cent - set up by a mutual friend, Gabriella - a second date (same girl as last week's blog)

Where: 50 Cent - HiHo Cheeseburger in Beverly Hills at 5pm, Gabriella - Bodega Wine Bar in Santa Monica at 7pm

This was a week of highs and lows. At first, I was feeling confident, with a date set for Thursday night with a professional dancer who was making me feel all types of ways from her pictures. "Wow, this Date A Week thing is EASY," I thought to myself as I looked down at my phone to see her cancel just hours before our date. "No worries, how about tomorrow instead?" I texted back casually. As the hours passed by, and no response came, I became worried that she had been kidnapped, or eaten by a group of professional-dancer-eating-piranhas. When I checked Instagram and saw her posting about how much fun she was having out with her friends, I realized something even worse had happened - I was being ghosted. "Not a problem," I lied to myself as I cried to some emotional Drake music. I had been putting in the work on Hinge and had plenty of options for the rest of the week."

I proceeded to be denied by 5 consecutive girls: one had a friend in town, one wasn't feeling too well, one had left her refrigerator running. I heard every excuse in the book. By Saturday morning, I had to face the harsh truth - I was simply ugly.

With morale low, and the blog deadline being 16 hours away, my friend suggested her bestie from home who was visiting Santa Monica for the weekend (we're calling her 50 Cent). As soon as I confirmed a 5pm dinner with 50 Cent, my phone buzzed with an extremely delayed text response from Gabriella of last week's blog, who was free for 7pm drinks in Santa Monica. All of a sudden, I had transformed from Ugly Betty to the most desirable bachelor in all of Southern California.

When I picked up 50 Cent, my initial impression of her was mixed. She was very nice and personable, with conversation coming easily during our car ride together. Maybe the word "ferociously" is more accurate than "easily", as I noticed that 50 Cent LOVED asking me questions. Any time there was a lull in the conversation (and by "lull" I mean a 3-second pause), she would come up with a brand new, unrelated topic. I appreciated her energy and genuine interest, but also felt our time together wasn't as relaxed or natural as I was hoping for.

Unfortunately, I also didn't feel a physical attraction towards 50 Cent, and quickly realized that this wouldn't be something I would want to pursue beyond a first date. With that in mind, I made it my goal to get to know her better as a person, and had a fun time discussing her upbringing, hobbies, and passions. I came to appreciate learning more about her and could see myself being friends with her, even though a relationship wouldn't be in our future.

Date #2 of the night with Gabriella started right where we left off last week, with Gabriella much more open and willing to share funny stories about herself (including how she met Shaq at her local gym and once saved her high school class president while he was blacked out). As we worked our way through a bottle of wine together, I could also feel Gabriella starting to flirt with me more and more, to the point that I even started to forgive her for hating Star Wars.

Although we still seemed not to have much in common, our conversation felt extremely natural and fun, way beyond what I had expected on a second date. Fueled by red wine and the past week of denial, I boldly asked her if she wanted to watch a movie at my place, even suggesting a Zac Efron film of her choice (that's how you know I'm in Simp Mode). She turned me down in the nicest way possible (which my fragile ego appreciated), suggesting we save that for next time and go for a late-night walk on the beach instead. However, what I thought was going to be an innocent walk on the beach turned into some late-night naughtiness, as we started getting freaky in a lifeguard stand. Just as I was starting to worry about sand in uncomfortable places, we noticed a homeless man watching us 3 feet away, which is not exactly nature's best aphrodisiac. That effectively cut our night short, but we agreed that we should get drinks and watch a movie together next weekend. I was really surprised by the growth I felt between Gabriella and me after a slow start to our first date, and am looking forward to potentially hanging out with her more soon. 

Overall Experience:

50 Cent - ⭐️⭐️⭐️

Gabriella - ⭐️⭐️⭐️⭐️.5

Future for us:

50 Cent - a question-filled friendship Gabriella - possibly a threesome with a homeless man

Next Week: Hopefully I don't get turned down 6 more times!


Key Takeaways: All in all, I learned I don’t like FaceTime dates and I wish him luck in his future.


Name: Rick because it seems like he should be named Rick, he seems like a Rick

Length of date: 1 hour

How the date was obtained: Bumble

Where: Over Facetime

Well, Rick started out late to the date. We were supposed to talk at 7:00 PM and he didn’t get back to me until 7:15 to begin our FaceTime, which I didn’t really dig (he had dog issues so I get it, but ya know, I like punctuality). Then we couldn’t get the FaceTime to work within Bumble so we had to exchange numbers and then do FaceTime through our phones. So by the time we actually talked, it was around 7:20…

The technology stuff was kind of awkward and he was making dinner, which was fine but it also made him distracted, and therefore it was hard to connect to him. I just didn’t feel like he was really invested in listening to me.

I was turned off from the beginning so I just resorted to asking him a ton of questions and getting him to talk about himself so I didn’t need to talk. I was really just biding my time for an hour since I felt like that was the respectful thing to do, but I knew from the beginning that we probably weren’t a match. He seems like a nice guy but just not a guy for me. He talked about drinking a lot and since I’m sober that was a turn-off. He's also dog-sitting a really big, hairy dog, and since I’m allergic to dogs that was also a turn-off. Most importantly, he didn’t ask me any deep or personal questions which made me feel even more like he wasn’t invested in learning about me - another turnoff.

Overall Experience:


The future for us… I’m cool if we never meet again

Next Week: I sent a note through bumble wishing him the best of luck and he sent a nice, similar note back. The end.


bottom of page