The Absolute Best Date I Have Ever Been On


I feel like I have a reputation when it comes to relationships and romance. As in, I’m not a romantic and I hate the mushy cheesy stuff. Which is honestly, true. Cheesy stuff seems excessive to me and makes me feel awkward.

But that doesn’t mean that I don’t want to fall in love or to date guys (well… right now I’m enjoying this whole focusing on myself thing, but you all know what I mean!). I have been “in love” twice, and I have had my fair share of dates and romances.

And even though I may have only shared the stories of the completely horrific dates on here, like the time a guy followed me twenty blocks, or the time a guy was horrifically racist, it doesn’t mean that all my dates suck and that every man I date is Nick Viall adjacent. I actually go on good dates (sometimes…), and since it is Valentine’s Day and I don’t want you all to think that I’m a total cynic, I have a story for all of you.

I’m going to tell you the story of the best date I have ever been on.

I think when people envision perfect dates, they expect literal fireworks, and a horse drawn carriage, or something of that sort. Some crazy Bachelor-level romantic shit involving helicopters.

I’m not really that type of girl…and this isn’t the case.

I’ve told you guys about the worst dates, now it’s time for the story of the best. Happy Valentine’s Day, guys.

I had met this guy in one of my classes in undergrad, and he was ridiculously handsome. We were friends, and we always sat by each other in class and talked. Although we always talked, we had kept each other at a safe, but comfortable distance even though we were obviously attracted to each other. Slowly but surely, we began texting more and more, and then I added him on Snapchat. I think that was the catalyst for things to happen between us, because we kept Snapchatting, until eventually we made plans to go out for a drink that night.

I had joked that he owed me fries and beer (two of my favorite things on this planet), and he happily obliged. He was at the gym as I was getting ready beforehand. Jojo was doing Microbiology homework as I curled my hair whilst sitting on the bedroom floor. I did my makeup super quickly, and threw a bunch of things into my fringed bucket bag.

That night, I wore my hunter green jeggings, my brown ankle booties, and a crochet crop top. I paired that with a denim jacket and curled my hair in loose, messy curls. And I remember that I wore KVD’s Lolita, because that is my classic date lipstick.

I sent him a Snapchat of me looking super cute, and then he sent one back saying that he was going to shower and get ready after going to the gym. I hung out with Jojo for a bit, and then dragged her to the lobby of our building as I waited for him to pick me up.

I was nervous.

You see, the thing with dates is that I don’t get nervous unless I really like them. And I really liked this guy.

He arrived, and then I headed outside. He picked me up in his Prius, and he asked me where I wanted to go.

Alright, I’m not going to go into specific details of our conversation because I believe it’s private…and also because we talked for a long time during this whole ass date. But I’ll detail the main parts.

I suggested a bar in Wicker Park, as it is my favorite neighborhood in all of Chicago. Seriously…it’s my hood. He asked me if I had gone to any bars in the South Loop, and I said no. We decided to avoid Little Italy, and so he suggested that we go to The Scout. He said that we could catch glimpses of The Cubs playing one of the World Series games, and that The Scout has giant grilled cheeses.

Both of those things sold me.

As we drove, we talked about a bunch of different things, like how I worked with homeless people and how he loved being an EMT when he took a course. We talked about a bunch of different things, and as soon as we pulled up to the bar, he got out of his seat, and went to open the door for me. Which by the way, got him major bonus points. Yes, I can open my own damn door…but I liked it.

He opened the door to the bar, and we sat down. The waitress handed the menus, and he told me that he chose this place because he remembered that I was a vegetarian (at that time!) and wanted to make sure I had something I could eat! He went through the menu and pointed out vegetarian items, which I thought was incredibly sweet.

I ordered a grilled cheese (how could I not? They are HUGE) and he got a turkey burger with tots! He noticed that I forgot to order fries, so he said I could have some of his. Which I thought was extremely considerate and sweet. He ordered some dark ale with a slight coffee taste, and I got a Ruby Redbird. Grapefruit and beer…two of my faves!

We ended up talking in that bar, about everything and anything (I told you guys that I’m a lady! Some stuff is personal). He was so incredibly easy to talk to, and the conversation flowed effortlessly. Sometimes in life, you meet someone who understands you and exactly what you’re saying, even if you can’t word it cohesively. This was one of those moments. He was impeccably funny, and undeniably charming. We talked about literally everything, and I think that with him even talking about gravel would be fun.

We talked for so long that our waitress’ shift ended, and she left. We ended up about thirty minutes past midnight because the parking was about to end (yes, we sat in that bar for hours), and headed back to the car. But because this was the one night that my life was a romantic comedy, the night wasn’t over…as neither of us were tired.

“Do you want to drive down Lake Shore Drive and listen to music and hangout and talk?”

Literally one of my favorite things to do, in the entire world.

Driving down LSD while the city lights twinkled and the lake glitters is by far one of my favorite things to do. We drove around Chicago, as the lights flickered and the wind blew gently. We drove around and talked for hours, about everything and anything under the moon. And what made it even better….he played Childish Gambino and The Weeknd’s Trilogy. I feel like you guys should already understand how crucial that was, and how obvious it is that I am impressed by his music choice.

Once again, the perfect conversation and excitement continued. We kept talking about everything and the conversation was amazing. I think out of all the people that I’ve met, he’s one of the easiest people for me to be around.

“Do you know what the best view of the city is?” He asked me, after the two hours of driving around came to a close.


“On the top of the Maxwell Street parking garage. You wanna go?”

I nodded, as he turned on Halsted. We got to the parking garage, headed up the elevator, and turned to face the skyline.

“Why’d you bring me up here?” I asked, looking at him expectantly.

He looked at me, and smiled.

“Are you going to push me off this parking garage or something?” Don’t ever tell Jojo and Lauren that I said that foolish nonsense.

“You see…our Public Health class is on a curve, and you’re doing better than me…”

I laughed. Obviously I laughed. He was incredibly funny and charming, how could I not?


“Just wanted to show you the view.”

And no, he didn’t kiss me on the top of that parking garage, as the skyline illuminated behind us.

We got back in his Prius, and he drove me home.

Just kidding.

We drove back to his place, and….we watched The Princess Bride. I’m not lying to you guys. This wasn’t some Netflix and Chill nonsense. We literally watched The Princess Bride, and he knew every single line. We hung out, and continued to have more amazing conversation. Things with him were just like that, he was incredibly easy to talk to and even easier to be around.

And ladies don’t kiss and tell.

And that, you guys, is the story of the best date I have ever been on. Beer, amazing conversations, grilled cheese, fries, Lakeshore Drive, Childish Gambino, The Weeknd, The Chicago Skyline, and The Princess Bride. No helicopters, literal fireworks, roses, horse drawn carriages or extravagance. Just real, genuine chemistry and connection. And it’s one of the most unforgettable and best nights of my life.

So, as you can all see, my heart isn’t completely made of stone.

You see, the unforgettable times don’t need the bells and whistles to make them special, it just needs that one person that will make things memorable. And I think that’s what makes things the best. Not that cheesy romantic shit.

And I know you guys are going to ask if we still talk, and we don’t. And yes, we did see each other again after that date. I think people are under the false impression that all good times have to be associated with good people.

But the truth is this, even if someone isn’t in your life forever (or they change), doesn’t mean that the memories you have with them do.

You can have amazing memories with people who aren’t that amazing, or who aren’t around anymore. It doesn’t make the memories less unforgettable.

And I don’t think us not talking to each other anymore makes this date less amazing or my story less good, I think it’s a real ending to a real story. People come and go, and it’s a part of life.

Happy Valentine’s Day, guys!

What’s your dream date?




7 thoughts on “The Absolute Best Date I Have Ever Been On


    Liked by 1 person

    1. Wow! What a personal question. Luckily for you, I don’t shy away from those.

      Well, primarily it’s because of the fact that I’m twenty one years old and I just graduated college and am really focused on establishing a great career and my achievements, rather than just being someone’s wife. I think it also has a lot to with the fact that I’m self-fulfilled and don’t need a guy to make me feel validated or happy. A lot of people need validation from others, or a significant other to make them happy. I’m not one of those people.

      I actually have said on this blog before that I’m focusing on myself and following my destiny, as I feel like now is the proper time to do so. Which is unfortunate for the Stanford educated lawyer, the med student, the bio-engineer, and others knocking on my door. Because I’m perfectly happy writing my heart out and working on my career. But someday I’ll be married.

      Marriage is actually the absolute last thing on my mind, but thank you so much for asking!

      Liked by 2 people

      1. Haha oh doll. It was just a joking question to that ADORABLE date story. I got you on the not married thing 😂


  2. Awww Chrissey I love this!!! You painted such a beautiful picture here of a perfect and real and perfectly real date. This reminds me so much of me and my husband’s first date! We seriously just walked around the city and got donuts and played video games. It was so chill and so perfect. ❤

    Liked by 1 person

    1. I’m glad you enjoyed it Charlotte!! I think genuine and real dates are the absolute best! It isn’t necessary to have all the bells and whistles as long as you’re having fun with someone cool! And that date sounds suuuper cute and chill, and obviously unforgettable! You guys are the cutest couple, I swear.


  3. That sounds like an awesome date! I don’t think I’m really one for cheesy gestures either, mainly because to me doing the ‘traditional’ date stuff shows you don’t know the person that well…

    Julia // The Sunday Mode


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