
Restaurant Rating: 🦀🦀🦀 out of 5. I’m not gonna lie. I really dislike this new menu of Rough Rider. Which sucks because it used to be in my top 5. The drinks aren’t great anymore (they’re just weird) and the food isn’t exciting. The crab dip though, is divine, a saving grace. Service is still good! We will await the menu refresh.
Date Rating: 🔥🔥 out of 5. I’m not sure what compelled me to start dating again. It could be the romance novels. It could also be that the men hitting on me in public are terrifying and I deserve better than that. I just feel crazy affectionate and need an outlet. I set up a bunch of dates and I was looking like the old HB.
Calvin was up first. He’s 16 years older than me, has a gorgeous head of salt and pepper hair, and he golfs. I’m imagining how great we’d look in Tulum together this summer. He invites me out on a date immediately and I’m feeling the initiative. We don’t text much or call the days leading up to the date and maybe that was my first mistake because BOY, was this date awkward. And I’m blown because I typically have great first dates!
Calvin shows up after me and I scoot out of the booth to give him a hug because I look amazing and he was kind of quiet. We spend a few minutes looking at the menu in silence which didn’t exactly help because the menu sucked and we weren’t particularly excited about anything on it. We wanted the same drink but he said we both couldn’t get it so he ordered one that was super strong.
We have small talk about our families and what we do for work. It’s petty but a pink flag of mine is when you’re dating a transplant and he doesn’t have any friends. Most likely he’s using a dating app for them and he’s going to be boring. When I hear Calvin just moved from Utah and not only has a 9-5 but bartends AND drives Uber to meet people and keep busy, I knew this probably wasn’t going to work. He’s simply just not going to have the time for me. Plus, what are you running from that you want to be that busy?

I ask the dreaded question about how dating has been going and what he’s looking for. I find out he’s divorced but our dating outlooks are really similar. No pressure, just assess all opportunities as you experience them. He says he’s a hopeless romantic but doesn’t want to force anything. Sweet. He makes sure to tell me he asked me out because he was attracted to me and it’s in this moment I realize he hasn’t really asked me anything about myself and he probably doesn’t have any intention to. My thing is, why are you going to date this much younger if you’re not here to ball out? Even if hooking up is what you’re looking for, why not create a more entertaining environment to elicit that from me? They’re honestly so boring.
The conversation lags a bunch and it’s not in a companionable way. My back is ACHING because wow, I’m really gonna have to charm and work my way through this. I do not miss this. I start talking about travel and hear fabulous stories of him in Turks & Caicos, Scandinavia, and Chile. He’s been all over the world and has an impressive bucket list. He mentioned that he lived in Texas so I tell him I want to go to Austin since my friends made it look so fun. When Calvin says “Don’t get me wrong, I love Austin but the city has gone downhill since they’ve defunded the police. There’s a lot of homelessness lately.” I’m actually extremely proud of my lack of reaction. I just like people to be well-read. It’s not asking for much but it seems to continually evade me.
I get all of his travel recommendations and I give him some restaurant ones and he laments that he doesn’t necessarily explore Phoenix alone. I tell him it’s one of my favorite things to do by myself and he noncommittally tells me he’s going to try.

When we stared at each other in uninterrupted silence for 15 seconds, I wanted to dissolve. He wasn’t going to say SHIT and my mind had gone blank. The crab dip was spoiling in my stomach. Luckily, I remembered he had a dog and closed out the date with me asking about him. His face lit up.
I may not be looking for a boyfriend intentionally but I at least want to have fun! Where’s the laughter, the sweet casual touches, the flirting? God, I miss flirting terribly. I can take responsibility for this because we should have talked more before the date, maybe I wouldn’t have gone on it. At the same time, I’m grateful because clearly I’m rusty. We needed to dust off a bit before we got started. If we get started. Let’s see how date #2 for the week goes!